Teddy Roosevelt: The All-American Man

Meet America's most charismatic cowboy president.

Nov 09, 2023

Early life

Roosevelt was born on East 20th Street in New York City on October 27, 1858. The second of four children, Teddy was named after his father, who was a rich glass importer. Ted’s father was a profound influence on his life. He deeply admired his dad, and tried desperately to imitate, and perhaps even outcompete, him. Ted’s mother was Martha Bulloch, a Southern belle from Roswell, Georgia. She may have inspired the character Scarlett O’Hara in the famous book Gone with the Wind. Funny, articulate, and well-read, mother Roosevelt hosted a cultivated salon. She imbued her son with the love of words. Ted was a sickly child, and suffered from severe bouts of asthma. This kept him isolated from his peers. Because of this, he developed a combative, life-affirming personality even from a young age. His father encouraged him to exercise in the gym and overcome his ailments. This fostered Theodore’s lifelong love of the outdoors, which later influenced his pro-environment policies as president. Young Ted was enthralled by the beauty of nature. He loved to watch the birds. This was the beginning of his interest in natural history. He became an amateur taxidermist, and memorized the Latin names of the birds and animals by heart. He kept diaries, and saved his specimens in the family ice box. Going into adulthood, Roosevelt had ambitions to become a naturalist, although fate would have other plans.

College years

Theodore’s college years were very successful. He excelled in his academic studies, and eagerly enjoyed rowing and boxing. He was smitten by one beautiful woman, named Alice Hathaway Lee. She had countless suitors, and Teddy feared he would not be one of them. He did not always exude the masculine bravado that we know and love him for today. To capture her affections, the dashing young Theodore made connections with her family. For example, he chatted politics with her uncle. He purchased little Indian presents for her brother. Slowly but surely, Roosevelt managed to charm the young girl’s family. He finally won her hand in marriage shortly after graduating from Harvard in 1880. At this time, the flames of Roosevelt’s love for politics were kindled. Politics was a forbidden field for men of his social class. Despite these norms for New York gentlemen, Ted pursued his ambitions to become a professional politician.

New York reformer

In 1881, at the age of 23, Roosevelt ran as a Republican for the state legislature, and succeeded. Although he entered the office with conservative leanings, Teddy grew increasingly pro-labor after witnessing the appalling conditions of laborers in New York. This was his introduction to progressive politics, and he began to crusade in favor of the working man against Big Business. Tragedy struck on February 14, 1884, when Roosevelt’s mother and wife died on the same day. Teddy was devastated. “When my heart’s dearest died, the light from my life went forever,” he wrote mournfully. He never spoke of Alice Lee again. The pain was too much. Roosevelt abandoned his fledgling political career to find peace of mind out in the Western frontier.

Dakota territory

Ted left his young daughter Alice in the care of his sister, and went out West to become a rancher in Dakota territory. “This is where the romance of my life began,” he said. Roosevelt was deeply impressed by what he saw out West. Everyone worked hard, and no one asked for any favors. They were self-reliant, independent, free-spirited pioneers. It was the true spirit of American democracy. And Roosevelt loved it. It was his first taste of something outside the Northeast. It also forged his personal image as a rough-and-ready cowboy. He dressed in a buckskin for a famous photoshoot, although no one actually wore that. But it reinforced this tough-guy persona. Roosevelt’s time out West helped him to conquer many of his self-doubts, as he worked to ingratiate himself to the gruff cowboy lifestyle. “It taught a man self-reliance, hardiness, and the value of instant decision,” he later reflected of life on the cattle ranch.

Commissioner roles

Roosevelt returned to New York in 1886 to resume his political career and his former life. Although he lost the election, he won the heart of the ravishing Edith Kermit Carow, a childhood friend. She treated him like a mother, and, although he balked at this, he secretly appreciated it. She took care of the practical side of his life. Roosevelt had realistic expectations about success in life. “Do what you can, with what you have, where you are,” he loved to say. And Teddy himself did a lot with what he had. He became an instant success in politics. Roosevelt’s rise began when he received a role as commissioner, first of the Civil Service, and then for the New York City Police. During his tenure as a civil servant, from 1889 to 1895, the reform-minded Roosevelt cleaned out the corruption of the spoils system, which had previously favored partisanship over merit. As Police Commissioner, from 1895 to 1897, Roosevelt introduced modern technology to police work. This was just the first taste of the modernization of America that Roosevelt’s reign would oversee.

Spanish-American War

Roosevelt received yet another prestigious role when he was appointed Assistant Secretary of the Navy by President McKinley in 1897. A year later, the Maine, an American armored cruiser, blew up off the coast of Havana during Cuba’s war of independence against the Spanish Empire. Yellow journalism seized the opportunity to stoke the public’s hatred of the Spanish colonizers. This led to America’s war against Spain, what Teddy’s friend John Hay described as “a splendid little war.” Roosevelt was a leading advocate of America’s intervention on behalf of the Cubans seeking freedom. He resigned from the Navy, and formed the first-ever volunteer cavalry regiment. They were known as the Rough Riders. Few of them came from the educated East Coast, but most of these brave Americans came from the Southwest. They were tough as nails, and were a formidable threat to the Spanish. On July 1, 1898, Colonel Roosevelt and his Rough Riders became legends when they charged up San Juan Hill. It was a very important battle that led to the capture of Santiago, which ultimately ended the war. The Riders suffered the highest casualties of anyone else in the war, with nearly 20% killed or wounded. Ted himself was wounded slightly by shrapnel in his arm. Roosevelt described San Juan as “the great day of my life.” It solidified his status in the public imagination as a fearless, virile leader who would risk it all for a just cause. The memory of this battle contributed directly to Roosevelt’s ascendancy in US politics.

White House

He soon became governor of New York in 1898. Roosevelt’s governorship of the state was a microcosm for his later presidency. He supported taxes on the franchise of public utility corporations. He regulated workers’ hours. He implemented conservationist programs. He was so progressive that he alienated much of the Republican establishment. So they sidelined him, and Ted begrudgingly ran for vice president with William McKinley in 1900. Teddy mesmerized audiences with his off-the-cuff stump speaking. His speaking style was one of raw action and powerful motions. It was impossible not to watch. He once said that a political speech was like a circus poster: you need broad brush strokes and bright colors to capture people’s attention. Perhaps a shock to many modern listeners, Roosevelt spoke with a high-pitched, screeching voice on the few recordings that exist. Ultimately, the key to Roosevelt’s appeal was his personal embodiment of American greatness. McKinley and his running mate won in a crushing landslide. Republican Party bosses were not able to restrain Roosevelt’s irresistible charisma. On September 14, 1901, President McKinley was assassinated by an anarchist while attending the Pan-American Exposition in Buffalo, New York. The president died several days later, leaving Theodore as America’s new leader. He was mocked by McKinley’s political advisor, Mark Hanna, as “that damn cowboy.” Roosevelt introduced a new governing philosophy to the American presidency. After the Civil War, most American presidents were undistinguished, unremarkable figures who were subordinate to Congress. But Teddy imbued the role of chief executive with a bombastic grandiosity. He articulated what he called the “stewardship theory” of the presidency. He felt that, as president, he was the steward of the American people. He felt he had the right to enact the popular will, except when explicitly forbidden by law or the Constitution. “I did not usurp power,” Roosevelt insisted. “But I did greatly broaden the use of executive power.”

Trustbuster

President Roosevelt took a robust stance in the Northern Securities case. He intervened to break up a large railroad conglomerate, organized by E.H. Harriman and J.P. Morgan. They dominated the railroad industry in the West, but Teddy was not willing to accept this state of affairs. He set out to break up a monopoly. Roosevelt’s attitude toward trustbusting was an innovation in American political life. He introduced the idea that the federal government had a responsibility to ensure the public good by breaking up monopolies. Teddy denounced the Gilded Age titans of industry as “malefactors of great wealth.” He aggressively regulated them, earning the nickname Trustbuster. His administration filed 45 lawsuits against some of America’s largest corporations, including Standard Oil and American Tobacco. Most of them were successful.

Big Stick

Teddy’s boldness was not confined to domestic affairs. He believed strongly in American military interventions. On foreign policy, he issued his Roosevelt Corollary, which reserved the right of the United States to be the policeman of the Western Hemisphere. The essence of Roosevelt’s foreign policy was summarized by the following phrase: “Speak softy, and carry a big stick, and you will go far.” That was a West African proverb that he popularized. It was a perfect combination of diplomacy and force. The colloquial “Stick” he spoke of was America’s Navy. He sent it into the Caribbean to prevent the British and other European empires from interfering with those island nations, and maintaining order when revolutions broke out.

Panama Canal

A revolution broke out in the Colombian-owned colony of Panama in 1902. The US was interested in constructing a Panama Canal, which would be built across the isthmus of Central America. It was designed as a way of connecting the two coasts of the continental United States. This was done with America’s commercial interests in mind. Roosevelt wanted Panama to win its independence from Colombia. He felt that the country’s new-found freedom could provide an opportunity to assist America’s business interests. So he sent in battleships, and supported Panama’s revolution. Teddy’s forceful use of executive power in this regard was controversial. It was not clear that the commander-in-chief possessed the Constitutional authority to make such orders. Ted became the first American president to actually leave the country while in office. He personally inspected the Panama Canal, and sat on a steam shovel to throw dirt on his own. The Canal’s construction was an industrial miracle. It was built sooner than expected, and all under budget. The Canal began in 1904, and was completed at a cost of $380 million. It was the largest civil construction project ever undertaken by modern people. Although the Panama Canal opened after Roosevelt left office, Teddy considered it the jewel crown of his entire presidency. The Panama Canal was a paradigm shift in modern commerce and military defense. It changed how the two oceans interacted. Its significance can hardly be overstated.

Square Deal

In 1904, Ted was re-elected by 2.5 million votes, the largest up to that time. For his wife Edith and their six kids, it meant four more years in the White House. Roosevelt presented an ambitious domestic agenda, which he called the Square Deal. It sought to serve the public good, rather than special interests. “It is better for the government to help a poor man to make a living for his family, than it is for a rich man to make a profit for his company,” Ted declared. He pursued pro-labor policies. He helped the cause of black rights. Most notably, he supported conservation. “I recognize the right and duty of this generation to develop and use the natural resources of our land,” Teddy acknowledged. “But I do not recognize the right to waste them, or to rob them by wasteful use, the generations that come after us.” Under Roosevelt, the number of national parks doubled. He designated 125 million acres as national forests. He placed major reserves of natural resources under federal control. This was all based on Teddy’s elastic interpretation of his presidential powers. The saving of Pelican Island in Florida was one such example. Bird lovers asked him to save the swamp land. As a result, he made it the first of his 51 bird reserves. This was the genesis of the modern Fish and Wildlife Service.

Great White Fleet

In foreign affairs, President Roosevelt abided by his Big Stick ideology. And it worked marvelously. His first-rate diplomacy in the Russo-Japanese War made him the first American to win the Nobel Peace Prize. The strong-willed Teddy projected power on the international stage through America’s modernized Navy, known as the Great White Fleet. The Great White Fleet served many functions. It was a homage to America’s technological achievement, by showcasing the ability of the nation to reach any part of the world at will. It marked the United States’ glorious entry into global affairs. More specifically, because the US owned Hawaii and the Philippines as overseas colonies, it was also a way of projecting power against Japan in the Pacific. And it worked.

African expedition

In 1908, Roosevelt finished out his second term. His hand-picked successor, William Howard Taft, took office in 1909. After the White House, the adrenaline-surging Teddy traveled to Africa to collect specimens for the Smithsonian. He also wanted to hunt some big game. He wrote all about his jungle adventures in his books. Teddy clashed with Africa’s enormous wild animals. With rifle in hand, he loved the bold freedom of being a hunter. On one occasion, Teddy’s associates tied down a giant black bear to a tree. They urged Roosevelt to shoot, but he saw this as unsportsmanlike. He resolutely refused to shoot the animal. This scene was lampooned by a political cartoonist, which became the inspiration behind the Teddy Bear toy.

Bull Moose Party

Ted returned to the US just in time for the election of 1912. Roosevelt was deeply disappointed by William Howard Taft, who had proved more conservative than progressive. He was especially outraged by Taft’s reversal of his environmental policies. Teddy challenged Taft for the Republican nomination. Despite winning 75% of the primaries, the party establishment still supported their incumbent. So the larger-than-life Teddy Roosevelt decided to found his own political party: the National Progressives. It was the most progressive platform until Franklin D. Roosevelt’s New Deal in 1936. It provided for women’s suffrage, deregulation of trusts, employment compensation, and a modified health program. When a reporter asked him how he felt, Teddy boldly replied, “I feel as strong as bull moose.” That was the origin of the party’s famous nickname. On October 14, 1912, at the height of the Bull Moose campaign in Milwaukee, Wisconsin, Theodore Roosevelt was literally shot in the middle of a speech. He was standing up in a convertible. The bullet passed through his coat and through a glasses case, which was metal rimmed. It also ran through his thick pages of speech, which slowed down the trajectory of the bullet. When he coughed, there was no blood, so he figured his lungs were okay. Undaunted, the powerful masculine Teddy Roosevelt proceeded to the hall to make his speech. After an hour and a half, he went to the hospital. Teddy’s showmanship and bravery made him enormously popular. “I do not care a rap for being shot,” he defiantly declared. “It is a trade risk, which every prominent public man ought to accept as a matter of course.” Ted ultimately lost the election to Democrat Woodrow Wilson. But he still managed to get 27% of the popular vote, the highest of any third party in American history.

Brazil expedition

After losing election in 1912, the 55-year-old Roosevelt went on his last great adventure. He traveled to Brazil in search of an uncharted body of water, the River of Doubt. He nearly died on this expedition, but Roosevelt managed to actually find the water. The Brazilians named it Rio Roosevelt in his honor. However, the expedition left Teddy in poor health for the rest of his life. He lost 55 pounds, but he didn’t care about risks. He was smitten by the joy of life.

Death and legacy

By this time, Theodore’s strenuous life had taken its toll. He had many operations done because of complications from jungle fever. He lost hearing in his left ear, and had been blind in the left eye since 1908, the result of a boxing injury. He spent his final years at his colorful home in Sagamore Hill. The 60-year-old Roosevelt passed from this life on January 6, 1919. The cause of death was a blood clot in the heart. He was buried in Young’s Memorial Cemetery on Oyster Bay Long Island. Under Roosevelt’s unrivaled leadership, the United States cast the 20th century in its own image. It was the beginning of the American Century. The US first emerged as a global power, while the presidency and federal government were reshaped to deal with the new complexities of modern life. Teddy was not necessarily a perfect man, but, from his perspective, it was always the effort that counts. That was the message Roosevelt declared in his famous speech titled “The Strenuous Life”:

“It is not the critic who counts. Not the man who points out how the strong man stumbles, or where the doer of good deeds could have done them better. That credit belongs to the man in the arena, whose face is marred by dust, and sweat, and blood, who strives valiantly, who errs and comes short again and again, because there is no effort without error and shortcoming. But who does actually strive to do the deeds, who knows the great enthusiasms, the great devotions, who spends himself in a worthy cause, who at best knows in the end that triumph of high achievement, and who at worst, if he fails, at least fails daring great. So that his place shall never be with those cold and timid souls who know neither victory or defeat.”