I’ve read biographies about great men. I’d even call a few of them a “Giga-Chad” or a “Bull Moose”. But without a doubt, one man outclasses them all: Theodore Roosevelt. Now there is a man who seized life by the horns.
This post is all about Theodore, as well as the qualities that made him great. See below for a high-level table of contents. We’ll cover everything from Teddy’s childhood, his cattle ranching days in North Dakota, his brilliant but non-linear career path, and his post-presidency expeditions in Africa and the Amazon.
- The Rise of Theodore Roosevelt
- The Presidency and Prime of His Life
- Theodore’s Final Adventures
- 2 Key Takeaways
The Rise of the Bull Moose
Overcoming Childhood Adversity
In 1858, just prior to the Civl War, Theodore “Teddy” Roosevelt Jr. was born into a wealthy family on East 20th Street in Manhattan.
As a child, Theodore struggled with poor health. In fact, he could barely breathe because of severe asthma attacks.
Even though Theodore lacked physical strength, he showed intellectual curiosity. In particular, Theodore developed a fascination for nature. Not only did Theodore teach himself taxidermy, he also collected a “mini-museum” of animal specimens.
Theodore also loved reading. For example, he read hundreds of books about heroes going on adventures. He also read scientific books (i.e. Charles Darwin).
Roosevelt was too sick to attend school. As a result, his family hired private tutors. Theodore excelled in biology, history, French and German. Roosevelt also traveled extensively with his family on tours of Europe and Egypt.
Without a doubt, Teddy worshipped his father. Theodore Roosevelt Sr. was a prominent businessman. He founded the Museum of National History, and he frequently donated to city orphanages. He encouraged his son to dream big and live a strenuous life.
“Theodore, you have the mind, but you have not the body, and without the help of the body the mind cannot go as far as it should. You must make your body.”
Theodore Roosevelt Sr.
Despite his frail frame, Theodore took his father’s advice to heart. Theodore learned how to box. He also hit the weight room. Furthermore, Theodore built up endurance by hanging from gymnastic rings and parallel bars.
Bull Moose at Harvard University
In 1876, Theodore enrolled at Harvard University, where he studied natural history. The intellectual rigor, social networking, and self-discipline Theodore developed at Harvard were instrumental in shaping his career.
Although he didn’t achieve top grades, he became well-known for his breadth of interests. Theodore boxed, rowed, and lifted weights. Plus, he joined the Porcellian Club and the Alpha Delta Phi fraternity to expand his social connections.
However, Theodore’s stint at Harvard wasn’t without tragedy. His father sadly died in sophomore year. In his senior year, Roosevelt met his first wife, Alice Hathaway Lee. Shortly after graduating in 1880, they married and had a daughter.
The New York State Assembly
Theodore then attended Columbia Law School. Yet he quickly figured out that a law career wasn’t right for him. So he spent most of his time at Columbia writing his first book about naval strategy in the War of 1812. The theories in his book would later lead to the modernization of the U.S. Navy.
In 1882, Theodore got his first big break in politics. At just 23 years old, he won an election to serve as a representative in the New York State assembly.
Theodore focused on progressive issues like government reform, labor protections, and social welfare. He unquestionably ruffled a lot of feathers by challenging political machines (like Tammany Hall) and patronage systems. Peers in the Republican Party saw Roosevelt as a rising star with charisma and talent.
Roosevelt’s final year in the Assembly was marked by tragedy. Not only did his mother pass away from typhoid fever on Valentine’s Day 1884, his wife also died later that day from childbirth complications. This devastated Theodore so much that he abandoned New York and relocated to the Dakota Territory.
Bull Moose in Dakota: The Cattle Ranching Years (1884-1888)
Roosevelt first fell in love with the Dakota territory during a bison hunting trip in 1883. He was so enamored by the beautiful frontier that he decided to invest $14,000 ($438,000 in today’s dollars) into the booming cattle industry.
As mentioned above, the death of his wife and his mother drove Roosevelt to seek a fresh start out in the Dakota territory. He invested in a ranch (Elkhorn Ranch), and embraced the rancher’s life with enthusiasm. Roosevelt herded cattle, hunted for food, and lived an active life outdoors.
At first, the locals chuckled. They couldn’t believe a city slicker like Theodore Roosevelt could survive in the Badlands. But he gradually won them over through grit and perseverance.
It’s impossible to understate how much of an impact these years had on Theodore. Undoubtedly it was Dakota that shaped his conservation policies and solidified his commitment to protecting America’s national parks.
By the late 1880s, brutal winters and overgrazing destroyed Theodore’s ranching business. In fact, he lost half of his cattle during the winter of 1886-1887. Roosevelt decided to shutter his ranch so that he could revive his dormant political career.
2nd Marriage and the Civil Service Commission (1889-1895)
Roosevelt found love again. He married his childhood friend Edith Carow in 1886, with whom he had 5 children. They settled in Oyster Bay, Long Island.
After a failed run for New York City mayor in 1886, Theodore feared his political career was over. He retreated into his library to write his acclaimed book “Winning of the West”.
But actually Theodore’s political career was just getting started. Another favorable break came when President Benjamin Harrison appointed Roosevelt to the Civil Service Commission in 1889.
As a member of the Commission, Roosevelt was a vigorous advocate for the Pendleton Civil Service Act. In summary, he sought to ensure that U.S. government jobs were being filled based on merit instead of nepotism.
Theodore used his position to raise growing awareness about corruption in the government. This put him at odds with members of his own political party, but it also won him admiration from the public.
Bull Moose Cop: New York City Police Commissioner (1895-1897)
In 1895, Theodore made another unlikely career pivot. He was appointed the President of the New York City Police Commission.
In this new role, Theodore set out to reform the police department. Some of his accomplishments include:
- Walked cops’ routes at night
- Reformed the Police Academy
- Punished corrupt officers
- Promoted officers based on merit
- Standardized use of firearms
- Adopted bicycles and telephones
- Enforced laws that were often ignored (i.e. Sunday alcohol laws)
It was during this period that Roosevelt also met Jacob Riis, the famous journalist who documented the trials of impoverished immigrants living in tenements. This encounter would later influence Roosevelt “Square Deal” policy.
Bull Moose in War: The Navy and the Rough Riders (1897-1899)
Roosevelt’s upward ascent continued. The U.S. government appointed Theodore as Assistant Secretary of the Navy in 1897. Despite the “assistant” title, Theodore’s boss was in poor health. Therefore, Roosevelt wielded significant authority.
In 1898, the U.S. declared war against Spain. This was driven by Cuban independence and the explosion of the USS Maine in Havana. Roosevelt had always dreamed of glory in battle, and so he made another unorthodox career move. Shockingly, Roosevelt resigned from his post in the Navy to enlist in the Army.
Roosevelt eventually assumed command of the Rough Riders cavalry regiment. The regiment included a diverse group of volunteers across social castes. Soldiers included (i) Ivy Leaguers, (ii) frontiersmen, (iii) Native Americans, (iv) sheriffs, (v) miners, (vi) hunters, and (vii) New England aristocrats.
They fought their first battle at Las Guasimas. Shortly thereafter, they helped the Americans seize the stronghold of Santiago by bravely charging up San Juan Hill.
Straightaway, the Rough Riders became an overnight sensation in the press. Citizens everywhere celebrated the Rough Riders’ heroism. To that end, Colonel Roosevelt’s leadership during the war greatly boosted his national reputation.
The Bull Moose Presidency
Governorship and Vice Presidency (1899-1901)
In 1899, Roosevelt became governor of New York State. He focused on service reform and labor laws. Theodore learned a lot about corporate monopolies as well. However, Theodore’s reformist agenda pitted him against members of his own party, including NY state Republican Party boss Thomas C. Platt.
Republican Party leaders were desperate to neutralize Roosevelt’s progressive agenda in New York State. Therefore, they proposed that Roosevelt join President McKinley’s ticket as Vice President in the 1900 election.
And in a landslide election, President McKinley won a second term with Roosevelt as his running mate. However, the Vice President role, primarily ceremonial in nature, didn’t suit Roosevelt’s active personality. He had only been VP for ~6 months when a twist of fate suddenly changed Roosevelt’s life forever.
On September 6th 1901, an anarchist named Leon Czolgosz shot President McKinley point-blank in Buffalo. When Roosevelt heard the news of McKinley’s death, he was on vacation in Vermont. Roosevelt raced to Buffalo so that he could take the oath of office as the 26th President of the United States of America.
President of the United States (1901-1909)
From Elkhorn Ranch to the Oval Office, Roosevelt had truly come a long way. At just 42 years old, Theodore became the youngest person ever elected to the Presidency. Here are some of his major accomplishments in office:
Square Deal
- Argued that the American people deserved “a Square Deal” in political, industrial and social matters
- Advocated for the “3 C’s”: Control of Corporations, Consumer Protection, and Conservation of Natural Resources
- Broke up anticompetitive monopolies such as the Northern Securities Railroad
“Big Stick” Diplomacy
- Promoted imperialism, stating: “Speak Softly, and Carry a Big Stick”
- Modernized the U.S. Navy (the “Great White Fleet”)
- Asserted the right for the US to intervene in Latin American affairs
- Secured the rights to build the Panama Canal, a strategic waterway and shipping route that connected the Pacific and Atlantic Oceans
Russo-Japanese War (1906)
- Won the Nobel Peace Prize for negotiating the Treaty of Portsmouth, which ended the Russo-Japanese War of 1906
- Japan won a decisive victory that changed the balance of power in East Asia
Environmental Conservation
- Established numerous national parks, forests, and bird reserves
- The 1906 Antiquities Act proclaimed 18 new U.S. National Monuments
- His efforts laid the groundwork for the modern conservation movement
Bull Moose Adventures
The Smithsonian-Roosevelt African Expedition
After 7 stressful years in the Oval Office, many Presidents retreated to a quiet, simple existence. But not Theodore. True to his nature, Theodore embarked on his biggest adventure yet: a scientific expedition of East Africa.
The experienced crew launched their yearlong safari in the savannah of Kenya. Then, they traveled through the jungles and swamps of the Belgian Congo (now DR Congo). Lastly, they went up the Nile River to Sudan. Roosevelt and his team hunted over 11,000 animals, many of which were brought back to the United States for zoological study and display at the Museum of Natural History.
Yes, the expedition resulted in the mass murder of thousands of exotic African animals. However, it paradoxically contributed to conservation awareness following the release of Theodore’s book “African Game Trails”. I don’t agree with the indiscriminate hunting of 11,000 animals, but I am glad that the expedition paved the way to a golden age of conservation for endangered species.
European Tour and the Bull Moose Party
Theodore then embarked on a grand tour of Europe. He hobnobbed with heads of state such as King George V of the UK, Kaiser Wilhelm of Germany, and King Victor Emmanuel III of Italy. Theodore’s diplomatic charm impressed the Europeans, and also delighted the American public.
Theodore drew massive crowds in Europe. Additionally, in Oslo Norway he became the first American to receive the Nobel Peace Prize. He earned the award for his efforts to negotiate a peace treaty during the Russo-Japanese War.
President William Howard Taft, Roosevelt’s handpicked successor, pursued a conservative agenda. This angered Roosevelt, who decided to run for President again in 1912 under a new 3rd party (the Progressive Party). Theodore trail-blazed across the country, preaching a platform of (i) women’s right to vote, (ii) more regulation of monopolies, and (iii) social welfare programs.
Legend of the Bull Moose: The Assassination Attempt
On October 14, 1912, a deranged man named John Flammang Schrank tried to assassinate Roosevelt during one of his campaign speeches. Schrank shot Roosevelt in the chest, but the bullet was slowed by (i) the steel eyeglass case and (ii) the 50-page speech tucked in Roosevelt’s breast pocket. Like an absolute maniac, Theodore proceeded to give a rousing 90-min speech to the crowd before going to the hospital. The bullet remained in his chest for the rest of his life.
“Ladies and gentlemen, I don’t know whether you fully understand that I have just been shot; but it takes more than that to kill a Bull Moose.”
Theodore Roosevelt Jr.
The Progressive Party turned into the “Bull Moose” party. But the stars did not align. Theodore Roosevelt ultimately lost the election to Democrat Woodrow Wilson. That being said, Roosevelt’s Progressive Party (27% of votes) beat the Republican Party.
The Roosevelt-Rondon Amazon Expedition
After his defeat in the 1912 presidential election, Theodore Roosevelt longed for a new adventure. As luck would have it, the Brazilian government invited Teddy to explore the River of Doubt in the Amazon. Along with his son Kermit, Theodore formed an expedition crew that included Brazilian explorer Cândido Rondon.
The expedition faced incredible hardships, such as: (i) treacherous rapids, (ii) scarce food supplies, and (iii) nerve-wracking encounters with indigenous tribes. Roosevelt came down with tropical fever after a wound in his leg got infected. He got so sick that he almost committed suicide so that he wouldn’t hold up the expedition.
Overall, the expedition was successful because the crew discovered many new species. On the other hand, Theodore lamented that the expedition took 10 years off his life because the trip caused his childhood health problems to re-emerge.
World War I
Roosevelt raged against President Woodrow Wilson because the latter maintained a neutral stance during the early stages of World War I. Teddy firmly believed that the U.S. needed to protect democracy by fighting alongside Britain and France.
In 2024, we are sick of seeing politicians call for intervention in foreign wars “for the sake of democracy”. However, Roosevelt backed up his beliefs by trying to enlist in the U.S. army (he was denied due to old age). Even more impressive was that all four of Roosevelt’s sons actually served in World War I. This is a stark contrast to many modern politicians who send other people’s children to fight instead.
Theodore’s youngest son, Quentin, was a talented pilot in the US Army Air Service. In July 1918, Germans soldiers killed Quentin by shooting down his plane. Quentin’s death permanently broke Theodore’s heart.
Death of the Bull Moose
Teddy Roosevelt believed that war could bring out the best in men. However, Roosevelt couldn’t have imagined the destructive new technologies that emerged after his death: planes, tanks, missiles, machine guns, mustard gas, atom bombs…
Teddy’s health continued to deteriorate after his son died. Roosevelt passed away in his sleep in 1919 at the age of 60. A life cut short; and yet, it was a life filled with wild adventure, courageous exploits, and triumphant victories.
Become a Bull Moose
If you’re interested in learning more about Teddy Roosevelt’s life, check out Edmund Morris’ biography. You can buy the complete 3-book set on Amazon.
The two main things I learned from Theodore Roosevelt are the importance of (i) talent-stacking and (ii) living a strenuous life.
1. Talent-Stacking
Teddy trailblazed an unconventional, non-linear career. He held a variety of titles: politician, cattle rancher, police commissioner, war colonel, naturalist, and explorer. Teddy was America’s renaissance man; a classic talent-stacker. I believe these diverse experiences helped propel Teddy’s ascent to the Presidency.
It’s OK if your career path is not a straight shot up. You’re going to encounter setbacks. If you’re just getting started, then you should take some strategic risks in your career. Find your calling, and don’t settle. Keep moving forward, keep learning, and progress will follow.
You might note that Teddy came from a privileged background. Therefore, he wouldn’t have been able to achieve these accomplishments without wealth. There is some truth to this, but we can still copy his growth mindset. It can’t be disputed that Teddy invested his 20’s and early 30’s into learning new skills, pursuing his passions, and striving for greatness. You can do the same!
2. Strenuous Life
Teddy struggled with debilitating illness as a child. He knew that a sharp mind requires a strong body. So he lifted heavy weights and boxed in the ring. He (allegedly) wrestled bears in the Mountain West, and he led far-flung expeditions.
Teddy lived a strenuous, vigorous life. He was a romantic who pursued the great ideals and the great truths. You’d be hard pressed to find a modern-day politician or businessman who did the same.
The typical white collar office worker in 2024 isn’t living to their peak human potential. Cubicle work would have crushed Teddy’s soul. We can’t all move to a cattle ranch in North Dakota, but I urge you to step into the arena. Get active. Start searching for opportunities to break out of this corporate-induced malaise. The world belongs to those who are both physically (and mentally) strong.
Thanks for Reading About the Bull Moose
Thanks for reading. I hope you walk away from this deep-dive with a renewed appetite for adventure and self-improvement. If you enjoyed this post, please subscribe to my blog here!
Don’t Flinch, Don’t Fold, and Hit the Line Hard!
– Pertinax