The Rise of Theodore Roosevelt

by Edmund Morris

Troy Shu
Troy Shu
Updated at: May 01, 2024
The Rise of Theodore Roosevelt
The Rise of Theodore Roosevelt

Discover Theodore Roosevelt's remarkable life story and leadership legacy. This summary covers his resilience, intellectual curiosity, connection to nature, and innovative reforms. Explore how this visionary President's legacy endures.

What are the big ideas?

Rugged Individualism and Resilience

Theodore Roosevelt's childhood and early adulthood were marked by overcoming significant health challenges. His determination and resilience in the face of adversity, as well as his intellectual curiosity, shaped his character and laid the foundation for his later success in politics and environmental preservation.

Intellectual Curiosity Fuels Political Leadership

From an early age, Roosevelt's insatiable curiosity about the natural world and dedication to self-improvement through reading and exploration became central themes in his life. This intellectual rigor not only equipped him with knowledge but also provided the foundation for his later political ideologies and decisions.

Roosevelt's Father's Influence

The complex relationship between Roosevelt and his father, Theodore Roosevelt Sr., profoundly influenced his development. His father's blend of compassion and strict discipline shaped Roosevelt into a person who valued both kindness and high standards, impacting his approach to both personal challenges and public service.

Intimate Connection with Nature

Roosevelt's deep connection with nature was not only a source of personal solace but also an impetus for his later conservation efforts. His experiences in the Badlands and his passion for hunting and outdoor life deepened his understanding and appreciation for environmental preservation, influencing his presidential conservation policies.

Political Innovation and Reform

Throughout his political career, from the New York State Assembly to his time as President, Roosevelt consistently pushed for reforms and challenged existing political norms. His efforts in civil service reform, police reform in New York City, and his approach to handling both allies and adversaries illustrate his innovative approach to governance and politics.

Strategic and Pragmatic Leadership

Roosevelt's leadership style was marked by a unique blend of charisma, strategic thinking, and pragmatism. He was adept at reading political situations and making decisions that, while sometimes controversial, were calculated to advance his agendas in conservation, military preparedness, and national politics.

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Rugged Individualism and Resilience

Theodore Roosevelt overcame significant health challenges in his youth, forging a character of rugged individualism and resilience. Despite his physical frailty, he possessed an insatiable intellectual curiosity and boundless energy. This determination to push past his limitations would later propel him to great success in politics and environmental preservation.

As a sickly child, Roosevelt refused to be defined by his ailments. He embraced physical activity with fervor, from long walks to vigorous sports. This resilience in the face of adversity shaped his worldview - one that valued self-reliance, grit, and an unyielding spirit.

Roosevelt's intellectual pursuits also revealed an unwavering drive. Even as a young man, he tackled ambitious writing projects, meticulously researching and documenting every detail. This rugged individualism - the ability to set ambitious goals and see them through - foreshadowed his later achievements in shaping the American political landscape and conservation movement.

Here are specific examples from the context that support the key insight about Theodore Roosevelt's rugged individualism and resilience:

  • As a child, Roosevelt was described as having "superabundant" energy that worried his father, who feared it "may get the better of him." This suggests Roosevelt's boundless vitality and determination even from a young age.

  • At Harvard, Roosevelt was known for his "uncontrolled enthusiasms" and "spluttery" manner, yet his peers found him "fascinating" despite his "peculiarity." This demonstrates his resilience in the face of not fitting in with the social norms of the time.

  • When settling into his dorm room at Harvard, Roosevelt expressed delight at the cozy and comfortable space, showing his ability to make the best of his circumstances. He wrote, "I do not think there will be a room in College more handsome."

  • Despite being assigned to a less desirable ground-floor dormitory as a freshman, Roosevelt took a room on the second floor, demonstrating his independence and refusal to accept the traditional freshman assignment.

  • In a letter home, Roosevelt expressed deep gratitude for his happy upbringing, saying he had "literally never spent an unhappy day, unless by my own fault." This positive outlook and appreciation for his circumstances exemplifies his resilience.

The context highlights how Roosevelt's determination, intellectual curiosity, and ability to thrive in the face of adversity shaped his character from a young age, laying the foundation for his later success and impact.

Intellectual Curiosity Fuels Political Leadership

Roosevelt's intellectual curiosity and thirst for knowledge were the driving forces behind his rise to political leadership. From a young age, he immersed himself in wide-ranging subjects - from natural history to literature to political philosophy. This voracious learning not only expanded his understanding of the world, but also shaped his core beliefs and ideologies that would guide his decisions as a statesman.

Roosevelt's passion for exploration and self-improvement through reading equipped him with a diverse knowledge base. He did not simply accumulate facts, but rather synthesized this information into a coherent worldview. This intellectual rigor formed the foundation for his political philosophies, such as his views on the role of government, social reform, and America's place in the world.

Roosevelt's curiosity-fueled intellect was a key driver of his leadership. His ability to draw insights from a wide range of disciplines allowed him to tackle complex problems from multiple angles. This interdisciplinary approach enabled him to develop innovative solutions and make informed, principled decisions as a public servant. Ultimately, Roosevelt's lifelong dedication to learning and self-improvement was instrumental in shaping his transformative political legacy.

Unfortunately, the provided context does not contain any specific anecdotes, stories, or examples that directly support the key insight about Roosevelt's intellectual curiosity fueling his political leadership. The context is focused on Roosevelt's political activities and relationships, and does not delve into details about his intellectual development or how it shaped his political views and decisions. Without relevant examples from the given text, I cannot provide a satisfactory response to support the stated key insight. The context simply does not contain the necessary information to illustrate that point.

Roosevelt's Father's Influence

Theodore Roosevelt's father, Theodore Roosevelt Sr., had a profound influence on his development. The elder Roosevelt embodied a blend of compassion and strict discipline that shaped his son into a person who valued both kindness and high standards. This impacted how Roosevelt approached both his personal challenges and his public service.

Roosevelt's father instilled in him the importance of caring for others, while also demanding that he meet lofty expectations. This dual approach molded Roosevelt into a leader who could empathize with people's struggles, yet also push them to achieve their full potential. His father's influence imbued him with a unique combination of empathy and determination that would guide Roosevelt throughout his life.

The lessons learned from his father's example equipped Roosevelt to navigate both his personal trials and his public duties with a steadfast commitment to excellence and service. This well-rounded upbringing allowed Roosevelt to become a transformative figure who could connect with the common person while also driving ambitious reforms. His father's impact was fundamental in shaping the man who would leave an indelible mark on American history.

Unfortunately, the provided context does not contain any information about Theodore Roosevelt's relationship with his father or how it influenced his development. The context focuses on Roosevelt's intellectual activities and political career in the 1890s, and does not mention anything about his father or their relationship. Without relevant details from the context, I cannot provide any specific anecdotes, stories, or examples to support the given key insight. The context simply does not contain the necessary information to address this query.

Intimate Connection with Nature

Roosevelt's profound connection with nature was a driving force behind his later conservation efforts. His experiences in the Badlands, including his passion for hunting and outdoor life, deepened his understanding and appreciation for environmental preservation. This directly influenced his presidential conservation policies aimed at protecting America's natural resources.

Roosevelt's time in the Badlands opened his eyes to the rapid destruction of the local flora and fauna. He witnessed firsthand how unchecked development and hunting were devastating the once-thriving wilderness. This realization prompted him to take action to preserve the great game animals and other wildlife from extinction.

After returning east, Roosevelt quickly assembled a group of influential animal-lovers to discuss ways to address this pressing issue. This led to the founding of the Boone & Crockett Club, which became a prime motivational force behind major conservation efforts during Roosevelt's presidency. His deep reverence for nature, forged in the Badlands, was a key driver of his landmark policies to protect America's natural heritage.

Here are examples from the context that support the key insight about Roosevelt's intimate connection with nature:

  • Roosevelt had a profound, almost Indian veneration for trees, particularly the giant conifers he had encountered in the Rockies. Walking silently through the "luminous nave of pines, listening to invisible choirs of birds, he came close to religious rapture."

  • When Roosevelt visited the Badlands, he was sickened by the environmental damage he witnessed, including the dwindling populations of big game animals, the destruction of the beaver dams and ponds, the erosion of the grasslands, and the overall degradation of the once "teeming natural paradise." This realization prompted him to take action to preserve the native American wildlife.

  • Roosevelt's early conservationist instincts dated back to his childhood, when at age 9 he was "sorry the trees have been cut down." His passion for taxidermy as a teenager was a "passionate sort of preservation" of the natural world.

  • Roosevelt's love for the animals he killed is evident, as he professed that a certain amount of hunting by responsible sportsmen was necessary to maintain the balance of nature, rather than allowing unchecked destruction by "swinish game-butchers."

  • Roosevelt's solitary time in the Badlands during his 1887 trip, when his companions left early, allowed him to fully experience the devastation and prompted him to take action to preserve the environment upon his return.

Political Innovation and Reform

Theodore Roosevelt was a political innovator who consistently challenged the status quo throughout his career. He pushed for bold reforms to transform outdated systems and address pressing societal issues.

As a New York state legislator, Roosevelt championed civil service reform, working to professionalize the civil service and reduce political patronage. Later, as New York City police commissioner, he implemented innovative police reforms to root out corruption and improve public safety.

Roosevelt's approach to governance was marked by a willingness to take on entrenched interests and challenge the traditional ways of doing things. He was not afraid to clash with allies or adversaries if he believed it was necessary to advance his reform agenda. This innovative mindset allowed Roosevelt to drive meaningful change and leave a lasting impact, even in the face of staunch opposition.

Roosevelt's commitment to political innovation and reform was a defining characteristic of his career. He recognized the need for bold action to address the problems facing the country, and he was unafraid to disrupt the established order to achieve his goals. This willingness to challenge the status quo made Roosevelt a transformative figure in American politics.

Here are specific examples from the context that illustrate Roosevelt's innovative approach to politics and reform:

  • Civil Service Reform: The context notes that Roosevelt's first speech in the New York State Assembly was on the importance of civil service reform, where he advised against interfering in the Democratic party's internal deadlock, as "the voters of the State will worry along through without it." This shows his willingness to challenge political norms and avoid partisan maneuvering.

  • Police Reform in New York City: As Governor of New York, Roosevelt "geared the police force to ensure a rigorously honest election" during the 1900 presidential campaign. This demonstrates his commitment to reform and his innovative approach to governance, using the power of the executive to ensure the integrity of the electoral process.

  • Handling Allies and Adversaries: The context describes how Roosevelt navigated his relationship with Senator Platt, the Republican party boss. Despite their initial tensions, Roosevelt was able to establish a "cordial" working partnership, illustrating his ability to work constructively with political adversaries to achieve his reform agenda.

  • Publicity and Transparency: The context highlights Roosevelt's innovative use of the media, noting that his "15-minute talks with reporters, morning and afternoon" were "the happiest moments of the Governor's administration." This shows his commitment to transparency and using public communication to advance his political goals.

Overall, the examples from the context demonstrate how Roosevelt consistently challenged existing political norms and pushed for reform throughout his career, using a range of innovative approaches to governance and coalition-building.

Strategic and Pragmatic Leadership

Roosevelt was a strategic and pragmatic leader. He skillfully navigated political landscapes, making bold decisions to drive his ambitious agendas in areas like conservation and military preparedness.

Roosevelt possessed a unique blend of charisma and strategic thinking. He could read situations shrewdly and take calculated actions, even if they were controversial at times. His leadership was marked by a determination to advance his visions for the country.

For example, Roosevelt worked tirelessly to build up the U.S. Navy, warning against "peace at any price" and arguing that military strength was essential for promoting true peace. He maneuvered adeptly, using his position as Assistant Secretary of the Navy to lay the groundwork for naval expansion, even as the cautious President McKinley resisted war.

Roosevelt's pragmatism allowed him to make tough choices and take decisive action when needed. He was willing to challenge the status quo and push boundaries to achieve his goals, whether championing conservation efforts or preparing the nation for potential conflicts. This strategic leadership style made Roosevelt a formidable and influential figure in American politics.

Here are some examples from the context that illustrate Roosevelt's strategic and pragmatic leadership style:

  • Roosevelt used his position as Assistant Secretary of the Navy to advance his agenda of military preparedness. He gave a speech at the Naval War College in 1897 calling for a rapid buildup of the American Navy, dismissing concerns that this would tempt the U.S. into unnecessary war. Instead, he argued that military strength would "promote peace" by keeping foreign navies out of the Western Hemisphere.

  • Roosevelt cultivated relationships with influential figures like Captain Alfred Thayer Mahan and Commodore George Dewey to further his expansionist goals. The context notes that he "used" them "to advance his own interest, while also advancing their own."

  • Roosevelt surrounded himself with a network of "expansionists" in government, the military, and the media who shared his vision of making America a "world power." This "lobby" included Senators, naval officers, philosophers, and journalists who looked to Roosevelt for "inspiration" as he worked quietly behind the scenes.

  • Despite his bellicose rhetoric about the virtues of war, the context suggests Roosevelt was a pragmatic leader who recognized the need to balance military strength with diplomatic finesse. He warned against "too much 'doctrinaire' thinking" and the dangers of "educated men in whom education merely serves to soften the fiber."

The key terms illustrated here are strategic, referring to Roosevelt's ability to carefully position himself and his allies to achieve his objectives, and pragmatic, indicating his willingness to make practical, sometimes controversial decisions in service of those objectives, rather than adhering rigidly to ideology.


Let's take a look at some key quotes from "The Rise of Theodore Roosevelt" that resonated with readers.

In the tired hand of a dying man, Theodore Senior had written: "The 'Machine politicians' have shown their colors... I feel sorry for the country however as it shows the power of partisan politicians who think of nothing higher than their own interests, and I feel for your future. We cannot stand so corrupt a government for any great length of time.

A dying father's worried words convey his disappointment in the corrupt government, where selfish politicians prioritize their own interests over the nation's well-being. He fears for the country's future, foreseeing a collapse under such corrupt leadership. His sorrow is palpable as he warns of the dangers of prioritizing personal gain over the greater good.

It is not often that a man can make opportunities for himself. But he can put himself in such shape that when or if the opportunities come he is ready to take advantage of them.

To capitalize on opportunities, one must prepare themselves in advance. This involves developing the necessary skills, knowledge, and mindset to seize chances as they arise. By being proactive and putting in the effort, individuals can position themselves to take advantage of opportunities when they come along. In this way, they can turn luck into success.

Take care of your morals first, your health next, and finally your studies.

Prioritize your character and well-being before focusing on academic pursuits. A strong moral foundation and good health are essential for a successful and fulfilling life, while education is merely a means to achieve it. By putting first things first, you'll be better equipped to tackle challenges and make the most of your learning opportunities.

Comprehension Questions

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How well do you understand the key insights in "The Rise of Theodore Roosevelt"? Find out by answering the questions below. Try to answer the question yourself before revealing the answer! Mark the questions as done once you've answered them.

1. What personal trait is characterized by setting ambitious goals and seeing them through, often without much reliance on others?
2. How does embracing physical activity despite health challenges demonstrate a particular personality attribute?
3. What does an uncontrolled enthusiasm in academic and social settings suggest about a person's character?
4. What does finding contentment in less than ideal circumstances indicate about a person's outlook on life?
5. How does intellectual curiosity contribute to effective leadership?
6. What role does a wide knowledge base play in shaping political ideologies?
7. How can mastering a variety of disciplines assist a leader in problem-solving?
8. How does a blend of compassion and strict discipline influence a person's development?
9. What impact does embodying empathy and determination have on one's leadership style?
10. How can lessons of excellence and service from a familial influence affect an individual's approach to challenges?
11. How did personal experiences in natural environments influence conservation policies?
12. What effect did witnessing the destruction of natural habitats have on advocacy for environmental preservation?
13. What roles did a passion for the outdoors play in shaping conservation movements?
14. Why is it important to protect game animals and other wildlife from extinction?
15. How can experiencing natural settings lead to a heightened sense of responsibility towards environmental preservation?
16. What role did political innovation play in the transformation of outdated systems?
17. How can introducing reforms in the civil service impact the functioning of government?
18. What is the significance of using public communication in political governance?
19. What does it mean to be a strategic leader in the context of advancing an agenda?
20. How does pragmatic leadership differ from ideological leadership?
21. What is the role of forming alliances and networks in achieving leadership goals?
22. Can you explain the concept of using controversy as a strategic tool in leadership?

Action Questions

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"Knowledge without application is useless," Bruce Lee said. Answer the questions below to practice applying the key insights from "The Rise of Theodore Roosevelt". Mark the questions as done once you've answered them.

1. How can you foster resilience in your everyday life by embracing challenges that strengthen your self-reliance and grit?
2. What daily habits can you develop to enhance your intellectual curiosity and independent thinking?
3. How can fostering intellectual curiosity enhance your problem-solving abilities in your professional or personal life?
4. In what ways can a multidisciplinary approach to learning influence your decision-making processes?
5. How can you use the values of empathy and determination to improve your leadership skills in your current role?
6. In what ways can you balance compassion with discipline in your personal and professional relationships to foster growth and mutual respect?
7. What steps can you take to develop a closer relationship with your local environment, and how might this influence your actions towards its preservation?
8. How can you implement innovative approaches in your own community or workplace to challenge outdated systems or practices?
9. What can you do to foster a collaborative environment that encourages taking on challenging reforms, even when facing opposition?
10. How can you adopt a strategic approach to personal or professional challenges, using a blend of foresight and adaptability?

Chapter Notes

1: The Very Small Person

  • Theodore Roosevelt's Childhood: The chapter provides a detailed account of Theodore Roosevelt's childhood, from his birth in 1858 to his return from the Roosevelt family's Grand Tour of Europe in 1870. It highlights his early life, family background, health issues, and intellectual development.

  • Family Background: Theodore Roosevelt came from a well-established, wealthy Dutch-American family with a history of civic engagement and philanthropy. His father, Theodore Roosevelt Sr., was a prominent businessman and social reformer, while his mother, Mittie, was a Southern belle from a prominent Georgia family.

  • Health Challenges: From a young age, Theodore Roosevelt faced numerous health issues, including asthma, nervous diarrhea, and other ailments that often confined him to bed. These health challenges shaped his childhood experiences and influenced his later life and career.

  • Intellectual Curiosity: Even as a young child, Theodore Roosevelt exhibited an insatiable intellectual curiosity, particularly in the natural sciences. He kept detailed diaries, wrote "natural histories," and amassed a collection of specimens, earning him the nickname "the Roosevelt Museum of Natural History."

  • Relationship with Father: Theodore Roosevelt had a close, yet complex, relationship with his father. While he admired his father's physical vitality, philanthropic work, and strong discipline, he was also somewhat "afraid" of him, as his father's high standards and quick temper could be intimidating.

  • The Roosevelt Grand Tour: In 1869, the Roosevelt family embarked on an extensive Grand Tour of Europe, which lasted for over a year. This experience exposed the young Theodore to a wide range of cultural and historical sights, further fueling his intellectual interests and sense of adventure.

  • Homesickness and Illness: During the Grand Tour, Theodore Roosevelt struggled with severe homesickness and recurring health issues, including asthma attacks and gastrointestinal problems. These challenges tested his resilience and shaped his character.

  • Emerging Personality: The chapter hints at the emergence of Theodore Roosevelt's distinctive personality, including his patriotism, reverence for authority, and budding romantic interests, even at a young age.

2: The Mind, But Not the Body

  • Teedie's Physical Transformation: Teedie, a sickly and frail boy, underwent a rigorous physical transformation through exercise and bodybuilding under the guidance of his father. This was crucial in preparing him for the challenges he would face in the future.

  • Teedie's Intellectual Pursuits: Teedie was an avid reader and scholar, with a particular passion for natural history and science. He spent hours studying, collecting specimens, and engaging in taxidermy, much to the consternation of his family at times.

  • Teedie's Travels and Experiences: Teedie had the opportunity to travel extensively throughout Europe, North Africa, and the Middle East with his family. These experiences exposed him to diverse cultures, art, and architecture, and shaped his worldview and interests.

  • Teedie's Relationship with his Father: Teedie had a close and influential relationship with his father, Theodore Senior, who was a determined and ambitious man. Theodore Senior played a crucial role in guiding and challenging Teedie to develop both physically and intellectually.

  • Teedie's Adolescent Struggles: Despite his intellectual and physical progress, Teedie continued to struggle with health issues, particularly asthma and other respiratory problems. These challenges tested his resilience and determination.

  • Teedie's Social Relationships: Teedie developed close relationships with his siblings and extended family, as well as with his childhood friend, Edith Carow. These relationships provided him with a supportive social network during his formative years.

  • Teedie's Preparation for Harvard: Teedie's intense academic focus and physical training were driven by his goal of gaining admission to Harvard University, which he saw as a crucial step in his personal and professional development.

3: The Man with the Morning in His Face

  • Theodore Roosevelt's Arrival at Harvard: Theodore Roosevelt arrived at Harvard in 1876 as a passionate, energetic, and eccentric freshman. He was known for his intense interests, physical vigor, and occasional outbursts of temper. Despite initial skepticism from his peers, he gradually gained acceptance and popularity within the Harvard social circles.

  • Academics and Intellectual Pursuits: While not considered an exceptional student initially, Theodore Roosevelt proved to be a diligent and hardworking scholar. He excelled in his courses, particularly in natural history and the sciences, and published his first scientific works on the birds of the Adirondacks and Oyster Bay.

  • Social Life and Relationships: Theodore Roosevelt immersed himself in the social life of Harvard, joining exclusive clubs and cultivating relationships with the Boston elite, including the Saltonstall and Lee families. He also maintained a close relationship with his childhood friend, Edith Carow, and developed an interest in other young women in the Boston social circles.

  • Grief and Transition: The sudden death of Theodore's father, Theodore Roosevelt Sr., in 1878 had a profound impact on the young man. He struggled with intense grief and self-doubt, but ultimately channeled his energy into his studies and physical activities, determined to honor his father's memory and live up to his expectations.

  • Outdoor Pursuits and Mentorship: During the summer following his father's death, Theodore sought solace and guidance in the wilderness of Maine, where he met the rugged backwoodsman, Bill Sewall. Sewall's influence and the time spent in the outdoors helped shape Theodore's character and worldview, instilling in him a deep appreciation for nature and the "men of toil."

  • Emerging Sense of Identity and Purpose: As Theodore entered his junior year at Harvard, he continued to excel academically and socially, but also grappled with uncertainty about his future career path. His experiences with Sewall and the Saltonstall-Lee families helped him develop a stronger sense of identity and purpose, setting the stage for his future as a renowned naturalist, politician, and statesman.

4: The Swell in the Dog-Cart

Here are the key takeaways from the chapter:

  • Alice Lee's Beauty and Charm: Alice Lee is described as an exquisitely beautiful, graceful, and charming young woman who captivated Theodore Roosevelt when he first met her. She is portrayed as a "star of heaven" and a "pure flower" who bedazzled everyone around her with her "singular loveliness" and "unfailing sunny temperament."

  • Theodore's Ardent Courtship: Theodore fell deeply in love with Alice and pursued her with intense passion and determination, despite her initial reluctance and tendency to flirt and tease him. He made Alice the sole focus of his attention and affection, even to the point of neglecting his studies and other activities.

  • Obstacles and Setbacks in the Courtship: Theodore faced several challenges and setbacks in his courtship of Alice, including her initial rejection of his proposal, his own bouts of depression and insecurity, and concerns about his health and physical limitations.

  • Theodore's Transition to Politics: As Theodore's relationship with Alice progressed, he began to shift his focus from natural history to politics, recognizing that a career in government would be more practical and fulfilling than one in science.

  • Theodore's Engagement and Wedding Plans: After a prolonged and tumultuous courtship, Theodore and Alice finally became engaged, much to the delight of their families. They made plans for a fall wedding, despite some initial resistance from Alice's parents.

  • Theodore's Declining Health: Unbeknownst to most, Theodore was informed by a doctor that his heart was in poor condition and that he should avoid strenuous physical activity. However, Theodore defiantly rejected this advice, determined to live life to the fullest.

  • Theodore's Final Bachelor Adventures: In the months leading up to his wedding, Theodore embarked on a series of vigorous outdoor activities and a hunting trip to the American West, seemingly in an effort to prove his physical capabilities and enjoy his last days of freedom.

5: The Political Hack

Here are the key takeaways from the chapter:

  • Theodore Roosevelt's Political Beginnings: After his marriage to Alice Lee, Theodore Roosevelt began to immerse himself in New York City politics, despite his family's disapproval. He joined the Twenty-first District Republican Association, a group of "rough" politicians, and worked his way up within the party machine, even though this was seen as beneath his social status.

  • The Naval War of 1812: During this time, Theodore also worked diligently on his first major book, "The Naval War of 1812", which was a scholarly and impartial account of the war. The book was well-received and became a standard text on the subject, establishing Theodore as a serious writer and historian.

  • Balancing Politics and Writing: Theodore struggled to balance his political ambitions with his literary pursuits, spending long hours working on his book while also attending to his duties as a budding politician. He was elected to the New York State Assembly, despite his family's misgivings, and saw this as an opportunity to gain political power and influence.

  • Navigating the Political Machine: Theodore's entry into the political machine was facilitated by Joe Murray, a ward heeler who recognized Theodore's potential as a candidate who could appeal to both the "swells" and the working-class voters. Murray helped secure Theodore's nomination, despite the opposition of the party boss, Jake Hess.

  • Theodore's Independent Streak: Even as a young politician, Theodore demonstrated a willingness to challenge the party establishment and pursue his own agenda. He opposed the renomination of the incumbent Assemblyman, Trimble, and ran on a platform of being "strong Republican on State matters, but independent on local and municipal affairs."

  • Foreshadowing of Theodore's Future: The chapter suggests that Theodore's early political experiences and his ability to balance his literary and political pursuits foreshadowed his later success as a politician and writer, as well as his independent and reformist tendencies that would shape his career.

6: The Cyclone Assemblyman

  • Theodore Roosevelt's Arrival in Albany: Roosevelt arrived in Albany in January 1882 to take his seat in the New York State Assembly. He was the youngest member of the legislature, known for his flamboyant style and Harvard-influenced mannerisms, which earned him the nickname "Oscar Wilde."

  • The Legislative Deadlock: The Assembly was deadlocked for several weeks as the Democrats and Tammany Hall members refused to vote for a Republican Speaker, leaving the legislature unable to conduct business. Roosevelt saw this as politically advantageous for the Republicans, as it allowed them to avoid taking responsibility for any unpopular legislation.

  • Corruption in the Assembly: Roosevelt quickly became aware of the widespread corruption in the New York State legislature, with a third of the members being "venal." He encountered examples of "strike" bills, where legislators would introduce legislation with the intent of being bribed not to pass it.

  • The Westbrook Resolution: Roosevelt introduced a resolution calling for an investigation into the conduct of Attorney General Hamilton Ward and State Supreme Court Justice T.R. Westbrook, whom he accused of colluding with the wealthy financier Jay Gould to manipulate the legal system for personal gain. This resolution sparked a major political battle.

  • Roosevelt's Confrontational Style: Roosevelt's behavior in the Assembly was described as that of a "perfect nuisance," with his colleagues often having to restrain his impulsive and confrontational approach. He would yell at the Speaker, pound his desk, and fire back "with all the venom imaginary" when attacked.

  • Roosevelt's Political Triumph: Despite the efforts of the "black horse cavalry" to block his resolution, Roosevelt's persistence and the public outcry over the Westbrook-Ward scandal ultimately led to the Assembly voting to investigate the matter, cementing Roosevelt's reputation as a crusading reformer.

  • Roosevelt's Legislative Record: While Roosevelt gained fame as a crusader, he was less successful in passing his own legislative agenda, with the "Aldermanic Bill" being the only one of his bills to become law. He also took a conservative stance on some social legislation, opposing measures to raise wages for municipal workers and ban tenement cigar factories.

  • Roosevelt's Personal Growth: The experience of the legislative session had a profound impact on the young Roosevelt, who emerged from it with a newfound sense of purpose and energy. His family members, including his wife Alice, were drawn to his "glowing youth" and "superabundance of animal life."

7: The Fighting Cock

Here are the key takeaways from the chapter:

  • Theodore Roosevelt's Political Ascent: At the start of 1883, Theodore Roosevelt was nominated and approved as the Republican choice for Speaker of the New York State Assembly, despite being the youngest member. This rapid political rise was noted by political commentators across the country, who saw him as a rising star destined for higher office.

  • Clash with Grover Cleveland over the "Five-Cent Bill": Roosevelt initially supported a bill to reduce the Manhattan Elevated Railroad fare from 10 cents to 5 cents, but later reversed his position after Governor Grover Cleveland vetoed the bill on constitutional grounds. This reversal led to significant criticism of Roosevelt, but he ultimately defended his decision, showing courage and integrity.

  • Roosevelt's Role in Civil Service Reform: Roosevelt worked closely with Governor Cleveland to pass civil service reform legislation in New York, despite being a member of the opposing Republican party. This bipartisan cooperation helped advance the reform movement and contributed to Cleveland's later election as President.

  • Roosevelt's Combative Style and Tendency Towards Piety: The chapter highlights Roosevelt's combative and aggressive style in the Assembly, including his use of harsh language and personal attacks on opponents. It also notes his tendency towards piety and oversimplification of political issues, which sometimes made him seem ridiculous.

  • Preparations for the Badlands Trip: As the legislative session ended, Roosevelt began planning a trip to the Badlands of Dakota Territory to go buffalo hunting, spurred by a chance meeting with Commander Gorringe. This trip would mark a significant turning point in Roosevelt's life, as he sought adventure and respite from the stresses of political life.

  • Concerns from Alice Roosevelt: Roosevelt's wife Alice was apprehensive about his trip to the Badlands, given his recent bouts of illness and the remote, dangerous nature of the location. Her concerns highlight the personal sacrifices and anxieties that accompanied Roosevelt's political ambitions.

8: The Dude from New York

  • Roosevelt's Enthusiasm for the Badlands: The chapter describes Roosevelt's deep fascination and enthusiasm for the rugged, beautiful landscape of the Badlands. He is captivated by the vast, untamed wilderness, finding it a stark contrast to the crowded, noisy rooms he is used to in New York. The Badlands represent a sense of freedom and connection to nature that deeply appeals to Roosevelt.

  • Roosevelt's Impulsive Investment in Cattle Ranching: Despite his lack of business acumen, Roosevelt impulsively decides to invest a significant portion of his inheritance (one-third of $40,000) in a cattle ranching operation in the Badlands. This decision is driven more by his romantic vision of the West than by careful financial planning.

  • The Marquis de Morès and the Conflict in the Little Missouri Valley: The chapter introduces the Marquis de Morès, a French aristocrat who has arrived in the Badlands with grandiose plans to build a massive slaughterhouse and cattle empire. His ambitions clash with the interests of local frontiersmen, leading to a violent confrontation that results in the death of one of the men.

  • The Hardships of Buffalo Hunting: Roosevelt's attempts to hunt buffalo in the Badlands are fraught with difficulties, including inclement weather, treacherous terrain, and the scarcity of the animals themselves. Despite these challenges, Roosevelt remains undaunted and enthusiastic, even finding joy in the privations of the experience.

  • The Influence of Gregor Lang and Lincoln Lang: Gregor Lang, a Scottish rancher, and his son Lincoln, have a profound impact on Roosevelt during his time in the Badlands. Gregor provides valuable insights into the cattle business, while Lincoln is captivated by Roosevelt's energy and intellect, seeing him as a remarkable and influential figure.

  • Roosevelt's Emerging Vision for the West: Through his interactions with the Langs and his experiences in the Badlands, Roosevelt begins to develop a broader vision for the development and conservation of the West's natural resources. This vision reflects his belief in the importance of cooperation, responsible stewardship, and the balanced pursuit of economic and environmental interests.

9: The Honorable Gentleman

  • Theodore Roosevelt's Speakership Bid: Roosevelt was a candidate for Speaker of the New York State Assembly in 1883, but was ultimately defeated by Titus Sheard, who was backed by the Republican party machine. However, Roosevelt's defeat actually strengthened his political position, as he was able to secure key committee assignments and exert significant influence in the Assembly.

  • Roosevelt's Municipal Reform Agenda: As chairman of the Committee on Cities, Roosevelt introduced several bills aimed at breaking the power of political machines in New York City, including measures to increase liquor license fees, limit the city's borrowing, and centralize power in the mayor's office. His "Roosevelt Bill" to empower the mayor was a major legislative victory.

  • Roosevelt's Investigative Committee: Roosevelt chaired a special committee to investigate corruption in the New York City government. While the investigation faced significant obstruction from entrenched political interests, it laid the groundwork for future reform efforts.

  • The Tragic Death of Alice and Mittie: Just as Roosevelt was experiencing political success, he suffered a devastating personal tragedy when his wife, Alice, and his mother, Mittie, both died suddenly on the same day. This event had a profound and lasting impact on Roosevelt, leading him to suppress his memories of Alice and avoid discussing her in the future.

  • Roosevelt's Transformation: The loss of his wife and mother marked a turning point in Roosevelt's life, as he emerged from the experience a more hardened and cynical individual, having shed his "lingering naïveté." The chapter suggests that Alice's early death may have been a "kind" fate, as she may have been ill-suited to Roosevelt's complex personality in the long run.

10: The Delegate-at-Large

Here are the key takeaways from the chapter:

  • Aftermath of the Tragedy: After the deaths of Alice and Mittie, the Roosevelt family had to sell their mansion, and Theodore Roosevelt returned to work in Albany, throwing himself into his legislative duties as a way to cope with his grief.

  • Confrontation with Governor Cleveland: Roosevelt was shocked when Governor Grover Cleveland threatened to veto some of his city reform bills, leading to a confrontation between the two men with vastly different personalities and approaches.

  • Delegate-at-Large at the Republican Convention: Roosevelt was elected as a delegate-at-large to the 1884 Republican National Convention, where he and Henry Cabot Lodge led the Independent faction supporting George F. Edmunds, in an attempt to prevent the nomination of James G. Blaine.

  • Political Maneuvering at the Convention: Roosevelt and Lodge engaged in complex political maneuvering at the convention, trying to delay the nomination of Blaine and potentially swing the nomination to Edmunds or another reform candidate. However, their efforts ultimately failed, and Blaine was nominated.

  • Relationship with Henry Cabot Lodge: Roosevelt and Lodge formed a close friendship and political alliance at the convention, recognizing each other's talents and ambitions, and laying the foundation for a long-lasting partnership.

  • Disillusionment and Desire for Solitude: After the convention, Roosevelt was exhausted and disillusioned with the political process, and expressed a desire to retreat to the Badlands of Dakota to find solace and escape the "roar of Chicago."

11: The Cowboy of the Present

  • Solitude and Isolation in the Badlands: Roosevelt sought solitude and isolation in the Badlands, finding the "vastness and loneliness and their melancholy monotony" of the landscape to have a "strong fascination" for him. He built a ranch house in a remote location to escape the interruptions and noise of the Maltese Cross Ranch.

  • Transition from Naturalist to Cowboy: After abandoning his natural history studies for his late wife Alice, Roosevelt rediscovered his "precocious sensitivity to nature" in the Badlands. He embraced the cowboy lifestyle, dressing in buckskin and chaparajos, and spending his days riding across the prairie.

  • Confrontation with the Marquis de Morès: The Marquis de Morès, a powerful local figure, claimed ownership of the land where Roosevelt was building his ranch house. This led to a confrontation, with the Marquis threatening Roosevelt, who responded by directly challenging the Marquis's claims.

  • Hunting Expedition in the Big Horn Mountains: Roosevelt embarked on a lengthy hunting expedition in the Big Horn Mountains, where he killed a large number of animals, including several grizzly bears. This expedition helped him cope with the grief over his wife's death.

  • Political Turmoil and Disillusionment: Roosevelt's support for the Republican presidential candidate, James G. Blaine, despite his earlier misgivings, led to a backlash from the reform-minded Independents. This political turmoil and his subsequent defeat left Roosevelt disillusioned with politics, leading him to embrace the "cowboy of the present" over the "Statesman (?) of the past."

  • Harsh Winter in the Badlands: The extreme winter weather in the Badlands, with temperatures plummeting to 50 degrees below zero, posed a significant challenge for Roosevelt and his ranch hands. The harsh conditions and their impact on the landscape and cattle became a source of both fascination and depression for Roosevelt.

  • Symbolic Relationship between the Landscape and Roosevelt's Emotional State: Roosevelt perceived a deep connection between the "iron" and desolate qualities of the Badlands landscape and the "iron" in his own soul, as he grappled with the grief and disillusionment following his wife's death and his political setbacks.

12: The Four-Eyed Maverick

  • Hunting Trips of a Ranchman: Roosevelt's first published work, which was well-received and became a standard textbook on big-game hunting in the United States. The book shows signs of being hastily written, with repeated anecdotes and inaccurate zoological details, but it also demonstrates Roosevelt's love for and identity with all living things.

  • Physical and Emotional Transformation: During the arduous spring roundup, Roosevelt underwent a remarkable physical and spiritual transformation, becoming "rugged, bronzed, and in the prime of health." This change was accompanied by a newfound confidence and energy, as evidenced by his ability to outperform the seasoned cowboys.

  • Sagamore Hill: The name Roosevelt gave to his recently completed house in Oyster Bay, which he saw as a symbol of his roots and a place he would eventually return to and die. The house, though initially raw and angular, became a source of proprietary emotion and a representation of the enduring strength of his family.

  • Relationship with the Marquis de Morès: Despite some business disagreements, Roosevelt and the Marquis had a generally cordial relationship. However, a misunderstanding led the Marquis to believe that Roosevelt was plotting against him, resulting in a tense exchange of letters that nearly escalated into a duel. The confrontation ultimately fizzled out, and Roosevelt's reputation as a fair and honest man was further solidified.

  • Engagement to Edith Carow: After years of avoiding Edith, Roosevelt suddenly found himself drawn to her again, and the two became secretly engaged. The engagement was kept secret due to concerns about the propriety of Roosevelt remarrying so soon after the death of his first wife, Alice Lee.

  • Hunting to Hounds: Roosevelt enthusiastically took up the sport of hunting to hounds, which he saw as a way to engage in a "stern and manly" pursuit. Despite sustaining a serious injury during a hunt, he continued to participate with the same energy and determination that he had shown in his Western adventures.

13: The Long Arm of the Law

  • Roosevelt's Relationship with Edith Carow: Despite their efforts to keep their engagement secret, rumors about Roosevelt and Edith Carow's relationship began to spread. Roosevelt was conflicted about remarrying, as he still felt guilty about the memory of his first wife, Alice Lee. However, he ultimately decided to marry Edith, planning a quiet wedding in London in the winter.

  • Capture of the Horse Thieves: As a deputy sheriff, Roosevelt felt compelled to pursue and capture a group of horse thieves who had stolen his boat from the Elkhorn Ranch. This led to an eight-day boat chase down the icy Little Missouri River, culminating in the arrest of the thieves and their subsequent conviction.

  • Completion of the Benton Biography: Roosevelt worked diligently to complete his biography of Senator Thomas Hart Benton, despite the distractions of ranch life and his other responsibilities. The book was well-received, though Roosevelt had some doubts about its literary merit.

  • Increasing Domestic Responsibilities at Elkhorn: As Sewall and Dow's families grew with the birth of their children, Roosevelt began to feel like an outsider in his own ranch, as if it were no longer his own domain. This contributed to his growing sense of restlessness and desire to return East.

  • Concerns about the Badlands Cattle Industry: Roosevelt grew increasingly concerned about the long-term viability of the cattle industry in the Badlands, as the region experienced a severe drought and overgrazing of the range. This led him to consider ending his ranching venture and focusing his efforts elsewhere.

  • Shifting Political Ambitions: While in the Badlands, Roosevelt continued to contemplate his political future, including the possibility of accepting a position on the New York Board of Health. He also expressed a desire to raise a regiment of cowboys to fight in a potential war with Mexico, though this opportunity did not materialize.

  • Ominous Signs in the Badlands: As Roosevelt prepared to leave the Elkhorn Ranch, he observed various natural phenomena, such as the strange haze in the air and the early migration of birds and animals, which suggested that the region was bracing for a harsh winter. This foreshadowed the challenges that would face the ranch in his absence.

14: The Next Mayor of New York

  • Theodore Roosevelt's Unexpected Nomination for Mayor of New York: Despite initially believing the mayoral race was a "perfectly hopeless contest", Roosevelt was unexpectedly nominated as the Republican candidate for Mayor of New York. This nomination came as a surprise to Roosevelt, who had planned to travel to Europe for his honeymoon with Edith.

  • Roosevelt's Vigorous Campaign: Once nominated, Roosevelt ran an extremely active and energetic campaign, addressing multiple meetings and events each night across the city. He was determined to meet every issue head-on, even controversial topics like labor versus capital.

  • Henry George's Formidable Challenge: The Labor party candidate Henry George, known for his book "Progress and Poverty", proved to be a much stronger challenger than expected. George's platform resonated with many working-class voters, and he was able to attract a large and enthusiastic following.

  • The Mayoral Campaign as a High-Quality Debate: The 1886 mayoral campaign was widely praised as one of the finest in New York's history, with the three candidates - Roosevelt, George, and Hewitt - engaging in a substantive debate on important issues facing the city.

  • Roosevelt's Surprising Defeat: Despite his vigorous campaign, Roosevelt was ultimately defeated in the election, finishing a distant third behind Hewitt and George. This defeat was a significant blow to Roosevelt, who rarely discussed the campaign in later years.

  • Roosevelt's Honeymoon in London: Following his defeat, Roosevelt traveled to London for his wedding and honeymoon with Edith. During this time, he was warmly welcomed into British high society and had the opportunity to meet with various intellectual and political figures.

Interlude: Winter of the Blue Snow, 1886–1887

  • Severe Blizzard and Snowfall: The chapter describes a severe winter in the Badlands region in 1886-1887, with heavy snowfall, blizzards, and subzero temperatures. The snow was so fine and powdery that it hovered in the air, making it difficult for cattle to breathe. The snow drifts reached up to 100 feet deep, burying ranches and thousands of cattle alive.

  • Cattle Starvation and Desperation: The harsh winter conditions led to a severe shortage of food for the cattle. The cattle were forced to eat frozen, sandy roots, bitter sagebrush, and even the bark and twigs of trees. Some cattle became so desperate that they invaded the streets of Medora, trying to eat tar paper from the buildings.

  • Massive Cattle Mortality: The extreme cold, blizzards, and lack of food resulted in the deaths of thousands of cattle. Younger and weaker cattle, such as Texas dogies and Iowa yearlings, perished almost entirely. Even older, hardier range steers succumbed to the conditions, with their carcasses piling up in vacant lots.

  • Flood of Cattle Carcasses: As the snow finally began to melt in March, a massive flood of cattle carcasses was unleashed, with the bodies of tens of thousands of cattle being swept down the river, rolling and jostling in the current. This "river of death" roared on for days, haunting those who witnessed it.

  • Aftermath and Bone Picking: After the flood, cowboys went out to survey the devastation, with one reporting that he "never saw a live animal" on the first day. In the wake of the cowboys came wagons of "bone pickers" employed by fertilizer companies, who began the grim task of sorting and stacking the skeletons of the cattle that had perished in the Winter of the Blue Snow.

15: The Literary Feller

Here are the key takeaways from the chapter:

  • Roosevelt's Return from Europe: After a 15-week tour of Europe, Roosevelt returned to the U.S. in March 1887 with his wife Edith. He was in good health, but Edith was feeling unwell, likely due to an early pregnancy.

  • Bamie's Custody Battle: There was a dispute over the custody of Bamie's foster daughter Alice, with Edith insisting the child live at Sagamore Hill. This caused tension between Bamie and Edith.

  • Devastating Blizzards in the Badlands: The severe winter of 1886-87 devastated Roosevelt's cattle ranching business in the Badlands, with estimates of 65-85% of his herd perishing.

  • Founding of the Boone and Crockett Club: Disturbed by the destruction of wildlife in the West, Roosevelt founded the Boone and Crockett Club in 1888 to promote conservation and preservation of big game animals and their habitats.

  • Writing "Gouverneur Morris": Roosevelt worked on a biography of Gouverneur Morris in 1887, which received mixed reviews but demonstrated his skills as a biographer.

  • Conception of "The Winning of the West": In early 1888, Roosevelt conceived the idea for his magnum opus, a multi-volume history of the westward expansion of the United States, which he titled "The Winning of the West."

  • Prolific Writing Output: In addition to "The Winning of the West," Roosevelt produced a large volume of other writing in 1888, including essays, articles, and a book on ranch life.

  • Appointment as Civil Service Commissioner: Despite his political frustrations, Roosevelt was appointed as a Civil Service Commissioner by President Harrison in 1889, a position he accepted despite its low pay and potential unpopularity.

16: The Silver-Plated Reform Commissioner

Here are the key takeaways from the chapter:

  • Washington, D.C. in 1889: The city was a delightful place for the wealthy, with a thriving social scene and a leisurely pace of life for senior government officials. However, the working class and poor faced high costs of living and limited opportunities.

  • Theodore Roosevelt's Appointment as Civil Service Commissioner: Roosevelt was appointed to the Civil Service Commission by President Harrison, despite concerns from his Republican allies that it would damage his political future. Roosevelt was determined to actively enforce the civil service laws.

  • Civil Service Reform Movement: The civil service reform movement was a passionate cause that sought to restore principles of equal opportunity, merit-based appointments, and job security for federal employees. Roosevelt was a sincere believer in these principles.

  • Roosevelt's Aggressive Approach as Commissioner: Roosevelt immediately took an active and confrontational approach as Commissioner, investigating cases of corruption and political patronage, and dramatically publicizing his findings. This put him at odds with political spoilsmen like Postmaster General Wanamaker.

  • The House Investigation: A House committee investigation was launched into allegations of misconduct by the Civil Service Commission. Roosevelt dominated the hearings, defending his actions and emerging with his reputation enhanced, despite some criticism over his handling of the Shidy case.

  • Roosevelt's Ambition and Influence: While opposing a single-headed Civil Service Commission, Roosevelt was already eyeing the presidency, with observers predicting he would one day occupy the White House. His growing influence in Washington society and intellectual circles further demonstrated his rising stature.

  • The Influence of Mahan's "The Influence of Sea Power upon History": Roosevelt's reading of this book over a single weekend profoundly shaped his strategic vision, leading him to advocate for a major naval buildup and an assertive global role for the United States.

17: The Dear Old Beloved Brother

Here are the key takeaways from the chapter:

  • Elliott Roosevelt's Alcoholism and Scandal: Elliott Roosevelt, Theodore's brother, was struggling with alcoholism and had an affair with a servant girl named Katy Mann, which threatened to become a public scandal. Theodore tried to handle the situation discreetly, including attempting to pay Katy Mann to keep quiet, but Elliott's erratic behavior made it difficult.

  • Theodore Roosevelt's Investigation of Political Assessments in Baltimore: As Civil Service Commissioner, Theodore Roosevelt conducted an investigation into federal employees in Baltimore who were soliciting political contributions from their subordinates, which was illegal under the Civil Service Code. His report found evidence of widespread wrongdoing, but Postmaster General John Wanamaker refused to take action, leading to a public confrontation.

  • Conflict with Postmaster General Wanamaker: Roosevelt's confrontation with Wanamaker over the Baltimore investigation escalated into a public dispute, with Wanamaker attempting to discredit Roosevelt's findings. This led to a Congressional investigation that ultimately vindicated Roosevelt and exposed Wanamaker's attempts to cover up the wrongdoing.

  • Roosevelt's Advocacy for Civil Service Reform: Throughout his tenure as Civil Service Commissioner, Roosevelt was a tireless advocate for civil service reform, seeking to root out the spoils system and political patronage in government. His investigations and confrontations with political figures like Wanamaker were part of this broader effort.

  • Roosevelt's Changing Attitudes Towards Native Americans: During a tour of Indian reservations, Roosevelt was deeply disturbed by the poor conditions and the exploitation of Native Americans by the spoils system. This experience led him to develop a more compassionate and reformist attitude towards Native American issues.

  • Roosevelt's Disappointment with the 1892 Election: Roosevelt was disappointed when the Republican Party lost the 1892 presidential election to Grover Cleveland, as he had hoped to continue his work as Civil Service Commissioner under the Harrison administration. However, he took pride in knowing that he had not "flinched" from enforcing the law during his tenure.

18: The Universe Spinner

Here are the key takeaways from the chapter:

  • Americanism and the Frontier: Roosevelt saw the American identity and character as being forged in the frontier experience of the American West. He saw the expansion of Anglo-Saxon civilization across the continent as the "crowning and greatest achievement" of a grand racial saga. Turner's frontier thesis, which emphasized the role of the frontier environment in shaping the American character, was influential on Roosevelt's thinking.

  • Racial Imperialism: Roosevelt believed in the right and duty of the "higher races" to conquer and civilize the "lower races". He justified the violent displacement of Native Americans as a necessary step in the advancement of civilization, and foresaw a future where European colonial powers would be supplanted by the rising power of the Anglo-Saxon and Russian peoples.

  • Defining Americanism: Roosevelt was prolific in his efforts to define and promote his vision of "Americanism", which emphasized values like strength, individualism, and a restless energy. However, his writings on the subject were often repetitive and characterized by a combative, negative tone focused on attacking "un-American" elements rather than praising positive American virtues.

  • Personal and Political Ambition: Roosevelt was driven by a strong personal and political ambition, which manifested in his desire to take on high-profile roles like the New York City mayorship. His frustration at being unable to pursue these ambitions due to financial and family constraints is evident in the chapter.

  • Expansionism and the Spanish-American War: Roosevelt was eager to involve the United States in the Cuban revolution against Spain, seeing it as an opportunity to assert American power and influence on the world stage. This foreshadowed his later role in precipitating the Spanish-American War.

  • Intellectual Influences: Roosevelt's thinking was shaped by a wide range of intellectual influences, from the historian Frederick Jackson Turner to the writer Rudyard Kipling. He engaged actively with these thinkers, both praising and critiquing their ideas.

19: The Biggest Man in New York

Here are the key takeaways from the chapter:

  • Roosevelt's Appointment as Police Commissioner: Theodore Roosevelt was appointed as the president of the New York City Police Board in May 1895, along with three other commissioners. He was determined to root out corruption in the police force and enforce the law impartially, regardless of political or social status.

  • Corruption in the Police Department: The New York City Police Department was deeply corrupt, with widespread bribery, graft, and collusion between the police, politicians, and criminal elements. Saloons, brothels, and gambling houses paid regular "protection" money to police captains and inspectors.

  • Enforcement of the Sunday Excise Law: Roosevelt ordered the strict enforcement of the Sunday Excise Law, which prohibited the sale of alcohol on Sundays. This led to a major confrontation with the powerful saloon and liquor lobby, as well as the German-American community, who saw the law as discriminatory.

  • Roosevelt's Publicity Tactics: Roosevelt used dramatic tactics, such as midnight patrols and public trials of delinquent officers, to draw attention to his reform efforts and build public support. He actively courted the press and used his personal charisma to gain national attention.

  • Political Backlash and Consequences: Roosevelt's uncompromising enforcement of the Excise Law led to a political backlash, with the Republican Party and German-American voters turning against him. This threatened his political future and strained his relationships with his fellow commissioners.

  • Roosevelt's Ambition and Restraint: Despite his growing national reputation, Roosevelt was wary of being seen as overly ambitious for higher office, such as the presidency. He actively discouraged his friends from speculating about his political future, fearing that it would undermine his ability to focus on his current duties.

  • Exhaustion and Uncertainty: The intense pace of Roosevelt's work and the political opposition he faced took a toll on his health and emotional well-being. He expressed uncertainty about the long-term viability of his reform efforts and the impact on his political career.

20: The Snake in the Grass

Here are the key takeaways from the chapter:

  • Thomas Collier Platt's rise to power: Platt, an experienced Republican politician, had become the undisputed manager of the New York State Republican party by the mid-1890s. He was determined to use his political machine to control the newly consolidated city of Greater New York, which would double his powers of patronage.

  • Conflict between Roosevelt and Platt: Roosevelt, as Police Commissioner, clashed with Platt over the latter's attempts to use the police force for political purposes. Platt tried to pass legislation to remove Roosevelt from office, but Roosevelt was able to rally public support and block Platt's efforts.

  • Deadlock on the Police Board: Commissioner Andrew D. Parker, an ally of Platt, obstructed Roosevelt's efforts to reform the police force by refusing to approve promotions and other administrative actions. This created a deadlock on the Police Board that paralyzed the department.

  • Roosevelt's frustrations and ambitions: Roosevelt grew increasingly frustrated with the "grimy" work of municipal reform and the obstacles he faced on the Police Board. He began to see his future in national politics, particularly in the area of naval affairs, and sought to position himself for a position in the incoming McKinley administration.

  • The Republican National Convention of 1896: Roosevelt's political loyalties shifted during the convention, as he initially favored Thomas B. Reed for the presidential nomination but ultimately supported the eventual nominee, William McKinley. This reflected Roosevelt's pragmatic approach to politics and his desire to align himself with the winning candidate.

  • Roosevelt's desire to leave the Police Department: By the summer of 1896, Roosevelt had become disillusioned with his work as Police Commissioner and was looking for a way to move on to a new position, potentially as Assistant Secretary of the Navy under the incoming McKinley administration.

21: The Glorious Retreat

  • Roosevelt's Relationship with Mrs. Bellamy Storer: Roosevelt had known Mrs. Storer since his early Washington days, and she was a wealthy and formidable matron who had political influence. She treated Roosevelt in a motherly way and was fond of him, and Roosevelt tried to leverage her connections to secure a high-level post in Washington.

  • Roosevelt's Interactions with Mark Hanna: Hanna was the Republican Party Chairman and a powerful political boss. Roosevelt met with Hanna several times, and Hanna was initially hesitant to support Roosevelt's appointment as Assistant Secretary of the Navy due to concerns about Roosevelt's combative nature.

  • Bryan's Nomination and the Democratic Campaign: William Jennings Bryan's nomination as the Democratic presidential candidate caused alarm among Republicans, as he ran on a radical platform of free silver and populism. Roosevelt campaigned extensively against Bryan, portraying him as a demagogue and a threat to the established order.

  • Roosevelt's Efforts to Resolve the Police Department Deadlock: As Police Commissioner, Roosevelt was embroiled in a bitter feud with Commissioner Andrew D. Parker, who obstructed Roosevelt's efforts to promote his preferred candidates. Despite Roosevelt's attempts to resolve the deadlock, the situation remained unresolved when he left the position.

  • Roosevelt's Appointment as Assistant Secretary of the Navy: After a lengthy negotiation process involving various political figures, including Senator Thomas Platt, Roosevelt was ultimately appointed as Assistant Secretary of the Navy, a position he had long desired. However, McKinley was initially hesitant to appoint him due to concerns about Roosevelt's combative nature.

  • Roosevelt's Achievements as Police Commissioner: During his tenure as Police Commissioner, Roosevelt made significant improvements to the New York City Police Department, including depoliticizing and deethnicizing the force, improving discipline and morale, and reducing crime and corruption. However, his departure was seen as a "glorious retreat" by his adversary, Commissioner Parker.

22: The Hot Weather Secretary

Here are the key takeaways from the chapter:

  • Roosevelt's Nostalgia for his Boyhood: Theodore Roosevelt had a strong sense of nostalgia for his childhood and youth, which often surfaced during moments of personal fulfillment, such as when he became Assistant Secretary of the Navy. This nostalgia was shaped by his memories of his revered uncle James Bulloch, who built the Confederate warship Alabama, and his mother, who had instilled in him a fascination with ships and naval warfare.

  • Roosevelt's Relationship with Mahan: While Alfred Thayer Mahan's work on the influence of sea power is often credited with shaping Roosevelt's naval philosophy, the evidence suggests that Roosevelt's views on the importance of a strong navy predated Mahan's writings. In fact, Roosevelt had already written extensively on naval history and the need for American naval expansion before Mahan became a prominent figure.

  • Roosevelt's Expansionist Agenda: As Assistant Secretary of the Navy, Roosevelt worked quietly but diligently to advance an expansionist agenda, seeking to increase the size and power of the U.S. Navy and to position the United States as a global naval power. He cultivated a circle of influential expansionists, including Senators, naval officers, and intellectuals, who shared his vision of American imperialism.

  • Relationship with Secretary Long: Roosevelt's relationship with Secretary of the Navy John D. Long was complex. While Long was initially skeptical of Roosevelt's aggressive approach, he came to appreciate Roosevelt's energy and expertise, and gave him significant latitude to shape naval policy during his absence.

  • Appointment of Dewey to the Asiatic Squadron: One of Roosevelt's most significant achievements was maneuvering to have Commodore George Dewey appointed as commander of the Asiatic Squadron, despite Secretary Long's initial preference for a different officer. This appointment would prove crucial in the upcoming Spanish-American War.

  • Roosevelt's Influence and Popularity: By the end of 1897, Roosevelt had established himself as one of the most influential and well-known figures in the U.S. government, with a growing reputation for his energy, intellect, and expansionist views. However, some expressed concern that his aggressive approach and "national insomnia" could be detrimental to the country.

23: The Lieutenant Colonel

Here are the key takeaways from the chapter:

  • Theodore Roosevelt's Aggressive Preparations for War: As Assistant Secretary of the Navy, Roosevelt took aggressive steps to prepare the U.S. Navy for a potential war with Spain, including ordering ships to strategic locations, stockpiling ammunition and coal, and authorizing the purchase of merchant ships for conversion to warships. This was done without the full knowledge or approval of his superior, Secretary of the Navy John D. Long.

  • Roosevelt's Desire to Serve in the War: Despite his important role in the Navy Department, Roosevelt was determined to serve in the war effort on the front lines. He repeatedly sought a commission in the Army, eventually securing a position as Lieutenant Colonel in the First U.S. Volunteer Cavalry, known as the "Rough Riders."

  • The Sinking of the USS Maine and the Push for War: The mysterious sinking of the USS Maine in Havana Harbor in February 1898 heightened tensions between the U.S. and Spain, with Roosevelt firmly believing that Spain was responsible. This, combined with growing public outrage over Spain's treatment of Cuba, put increasing pressure on President McKinley to declare war.

  • McKinley's Attempts to Avoid War: President McKinley, despite the growing clamor for war, tried to find diplomatic solutions to the Cuban crisis, including proposing to buy the island from Spain and seeking a negotiated armistice. However, he was ultimately unable to prevent the U.S. from entering the war, as public and Congressional sentiment had turned strongly in favor of military action.

  • The Importance of Dewey's Victory in the Philippines: The decisive victory of Commodore George Dewey's Asiatic Squadron over the Spanish fleet in the Philippines was a major early success for the U.S. in the war, and was in part due to the preparatory work done by Roosevelt in the Navy Department.

  • Roosevelt's Resignation from the Navy Department: Despite pleas from his friends and colleagues to remain in the Navy Department, where his expertise was seen as invaluable, Roosevelt resigned his position to take up his commission with the Rough Riders, driven by a desire to prove his commitment to his principles and to experience the glory of combat.

24: The Rough Rider

Here are the key takeaways from the chapter:

  • Composition of the Rough Riders Regiment: The Rough Riders regiment was composed of a diverse group of men, including Ivy League students, cowboys, and high-profile athletes. Roosevelt specifically recruited these "gentleman rankers" to give the regiment a sense of "tone" and prestige.

  • Training and Discipline in Camp Wood: The Rough Riders underwent rigorous training at Camp Wood, including daily mounted drills, skirmish practice, and other military exercises. Roosevelt was in charge of much of the training, while Colonel Wood handled administrative duties. There were some challenges with discipline and drill, as the individualistic recruits struggled to adapt to military life.

  • Rivalry between Roosevelt and Wood: Although Wood was the official commander of the regiment, it became clear within a week that Roosevelt was the de facto leader. The men respected Roosevelt's drive and ambition, and Wood recognized that Roosevelt would likely replace him if the campaign lasted.

  • Journey to Tampa: The Rough Riders' journey from San Antonio to Tampa was a chaotic and uncomfortable experience, with the men crammed into trains for four days. Roosevelt worked to maintain discipline and provide for the men's needs during the trip.

  • Logistical Challenges in Tampa: The Rough Riders faced significant logistical challenges in Tampa, as the Army struggled to embark the troops and supplies onto the transport ships. Roosevelt and Wood had to fight to secure a spot on the ship Yucatán for their regiment.

  • Delays in Departure: The departure of the invasion force from Tampa was repeatedly delayed due to concerns about Spanish naval activity in the Gulf of Mexico. The Rough Riders were forced to wait on the ships for nearly a week, enduring poor conditions and growing increasingly impatient to get to Cuba.

25: The Wolf Rising in the Heart

  • The Rough Riders' Landing in Cuba: The Rough Riders, led by Theodore Roosevelt, landed at Daiquirí, Cuba, on June 22nd, 1898, as part of the U.S. invasion force. The landing was difficult, with soldiers having to jump from boats into the choppy surf, and horses being pushed into the water to swim to shore.

  • The Battle of Las Guásimas: On June 24th, the Rough Riders, along with other cavalry units, engaged Spanish forces at Las Guásimas. Despite heavy fire from Spanish snipers, the Americans were able to drive the Spanish back, with Roosevelt leading a charge that exposed the Spanish flank to crossfire.

  • The Assault on San Juan Heights: On July 1st, the Rough Riders and other units attacked the heavily fortified San Juan Heights, which guarded the approach to Santiago. After a long delay, Roosevelt led a charge up Kettle Hill, capturing it and then providing covering fire for the assault on San Juan Hill itself.

  • Roosevelt's Leadership and Heroism: Throughout the campaign, Roosevelt displayed exceptional leadership and personal bravery, often leading charges and exposing himself to enemy fire. His actions earned him widespread praise and the respect of his men, as well as a potential nomination for Governor of New York.

  • The Aftermath and Evacuation: After the capture of San Juan Heights, the U.S. forces faced a difficult siege of Santiago, with disease and lack of supplies taking a heavy toll. Roosevelt eventually wrote a "round-robin" letter criticizing the army's leadership, which led to the evacuation of the troops from Cuba.

  • The Significance of the Rough Riders' Achievements: The Rough Riders' actions, particularly Roosevelt's leadership during the assault on San Juan Heights, were seen as a major triumph and helped cement Roosevelt's reputation as a war hero. Their success in storming a heavily fortified position was considered a remarkable military achievement.

26: The Most Famous Man in America

  • Roosevelt's Homecoming: When the Rough Riders returned from Cuba, Roosevelt was greeted as a hero by a large crowd at Montauk Point. The crowd cheered for "Teddy and the Rough Riders," showcasing Roosevelt's newfound fame and popularity.

  • Political Maneuvering: Despite his reluctance to discuss politics, Roosevelt authorized two secret nomination campaigns for the governorship of New York, one by the Republican machine led by Senator Platt, and another by the Independent party led by John Jay Chapman. This demonstrated Roosevelt's political savvy and ambition.

  • Residency Controversy: Roosevelt faced a potential disqualification from the gubernatorial race due to questions about his legal residency in New York. However, the Republican party, led by Elihu Root and Platt, worked to find a legal justification for his candidacy, highlighting the party's willingness to support Roosevelt's political aspirations.

  • Rough Rider Campaign: Roosevelt embarked on an extensive campaign tour, traveling across New York state and using his Rough Rider veterans as a visual symbol to connect with voters. His dynamic speeches and charismatic presence captivated audiences, contributing to his eventual victory.

  • Attack on Tammany Hall: Roosevelt made the corruption of the Tammany Hall political machine, led by Richard Croker, a central issue in his campaign. This allowed him to position himself as a reformer and champion of good government, further boosting his popularity.

  • Narrow Victory: Despite the odds and challenges, Roosevelt won the gubernatorial election by a narrow margin of 17,794 votes. This victory was seen as a triumph of his personality and campaign strategy over the discouraging political conditions.

  • Newfound Wealth and Influence: With his election as governor, Roosevelt gained a significant increase in income, including a state salary, lecture fees, and book royalties. This newfound wealth and influence further solidified his position as a rising political star.

27: The Boy Governor

  • Roosevelt's Relationship with Platt: Roosevelt was determined to maintain his independence as Governor while also working with Senator Platt, the "Easy Boss" of the Republican machine in New York. He sought to balance idealism and efficiency by publicly announcing his meetings with Platt and other organization leaders, ensuring transparency.

  • Franchise Tax Bill: Roosevelt clashed with Platt over the Ford Franchise Tax Bill, which aimed to tax corporations holding public franchises. After initially deferring to Platt's request for a study committee, Roosevelt ultimately forced the bill's passage through the legislature by issuing a special emergency message.

  • Roosevelt's Gubernatorial Accomplishments: Despite the tension with Platt, Roosevelt was able to achieve several progressive reforms during his first year as Governor, including passing a strong civil service law, labor legislation, and initiating an investigation into the Erie Canal scandal.

  • Publicity and the Press: Roosevelt's frequent, informal press conferences with reporters were unprecedented for a New York Governor at the time. He used these interactions to raise public awareness of the growing influence of corporations in politics, which he saw as a major threat.

  • Vice-Presidential Ambitions: As Roosevelt's popularity grew, there was speculation that he might be a candidate for Vice President in 1900. However, Roosevelt was initially reluctant to pursue this path, preferring to focus on his work as Governor and potentially run for reelection.

  • Cromwell Biography: During a brief summer vacation, Roosevelt completed a biography of Oliver Cromwell, drawing parallels between Cromwell's leadership and his own political approach as Governor.

  • Dewey's Homecoming Parade: Roosevelt played a prominent role in the grand parade celebrating Admiral Dewey's return from the Spanish-American War, cementing his status as a rising political figure.

28: The Man of Destiny

  • The Assassination Attempt: On October 14, 1912, while campaigning in Milwaukee, Theodore Roosevelt was shot in the chest by a deranged man named John Schrank. Despite being wounded, Roosevelt insisted on delivering his scheduled speech, which had been perforated by the bullet. He spoke for over 80 minutes before finally agreeing to seek medical attention.

  • Roosevelt's Resilience: Even after being shot, Roosevelt displayed remarkable resilience and determination, refusing to cancel his speech and instead delivering it despite his injury. This incident further cemented his reputation as a tough, indomitable figure.

  • Schrank's Motivations: Schrank's attack was motivated by a delusional belief that the ghost of William McKinley had called on him to assassinate Roosevelt to prevent him from serving a third term as president. Schrank left behind a note expressing this belief and his willingness to die for his country.

  • The Bullet's Trajectory: The bullet that struck Roosevelt had a remarkable trajectory, passing through several layers of clothing and other objects before lodging against his fourth right rib, just inches from his heart. Experts marveled at how the various impediments likely saved Roosevelt's life.

  • Edith Roosevelt's Reaction: Upon hearing of the assassination attempt, Edith Roosevelt immediately left the theater where she was watching a performance and rushed to be with her husband, demonstrating the deep bond between the two.

  • Roosevelt's Continued Campaigning: Despite the severity of his injury, Roosevelt insisted on continuing his campaign schedule, underscoring his tireless work ethic and commitment to his political goals.

Key Terms:

  • Assassination Attempt: The act of trying to kill a prominent public figure, in this case Theodore Roosevelt.
  • Resilience: The ability to withstand or recover quickly from difficult conditions or challenges.
  • Delusional: A belief or impression that is not in accord with reality and is not explained by a person's cultural context.
  • Trajectory: The path followed by a projectile, such as a bullet, through the air.
  • Impediment: Something that interferes with or delays progress.


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