Spring Sale: up to 50% on selected models

The Transformation of Teddy Roosevelt

How willpower turned a sickly kid into the President of the United States.
The Transformation of Teddy Roosevelt
The Transformation of Teddy Roosevelt

Some men loom larger in history than others. The four faces on Mount Rushmore represent some of the greatest leaders in the history of the United States. They earned their place there through character—and using the pressures of their circumstances to refine themselves into the icons they would become.

Washington, whose long, bloody fight in the Revolutionary war gave him the resolve to lead a nation at its birth. Jefferson, who in the heat of the struggle for independence, forged some of the most famous words in the world—the Declaration of Independence—and grew the country he helped to make free. Lincoln, whose humble log cabin beginnings gave him the grit that made him one of America’s most tenacious presidents, fighting to keep the country together at a time when it was nearly torn apart.

And then there is Theodore Roosevelt, 25th president of the United States. A man whose life was a study in contrasts. Part politician and part cowboy, he was dedicated to strenuous physicality and wrote 35 books. He fought in the Spanish-American war and won the Nobel Peace Prize for arranging the end of the Russo-Japanese war.


Earning His Place in History

Roosevelt's fame did not come from the same historical moments as the others. There was no Revolution or Civil War to secure his place in history. He wasn’t even elected to be President. But the greatness of his spirit earned him his place there. His dedication to overcoming obstacles transformed him from a sickly, home-schooled boy into the iconic, rough-riding figure that history knows today.

It was a transformation driven by nothing but Roosevelt’s own desire. There were many reasons why many would have chosen an easier path, from the luxury he was born into to the physical weakness he was born with. But when life handed Theodore Roosevelt a challenge, he used it as an opportunity to shape himself into something greater—and, just like the mountains he later climbed in life, every childhood obstacle was an opportunity to grow stronger and better.

I wish to preach the doctrine of the strenuous life, the life of toil and effort, of labor and strife; to preach that highest form of success which comes, not to the man who desires mere easy peace, but to the man who does not shrink from danger, from hardship, or from bitter toil, and who out of these wins the splendid ultimate triumph.-Teddy Roosevelt

The Choice for Self-Improvement

Born on Oct. 27, 1858, Theodore Roosevelt Jr. was the second of four children in a wealthy family. He came into the world as the son of a socialite mother and businessman and philanthropist father, with family wealth that enabled him to grow up more privileged than most. At least on the surface.

As a boy, he was schooled at home by his parents and private tutors and mid-way through college he inherited a fortune that meant he would never have to work again. But he was not so lucky in all aspects of his life. 

As a child, Roosevelt was sickly. He was nearsighted and not allowed to roughhouse with other boys, suffering from asthma that at at the time could be a death sentence. There was no cure from doctors, and that made every night a battle with fear for young Roosevelt, who was forced to sleep sitting up and struggle against the feeling of being suffocated. But inside was a bright and curious boy. And it was a challenge from his father one day that would spark the change that would lead him to bring what he had to offer to the world. 

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. I am giving you the tools, but it is up to you to make your body. -Teddy Roosevelt Sr.

When Roosevelt heard those words from his father he responded, “I will make my body.” It was the first sign of the self-made man he would become. With his sights fixed on strength, he and his father set about building a gym where Roosevelt could build a body as strong as his mind. It marked the beginning of Roosevelt’s dedication to what he later called, “The strenuous life.” A life of vigor and physical exercise that fueled his energetic approach to governing—and whatever other adventures he threw himself into.


Learning to Love the Struggle

As Roosevelt pushed himself to hike, box and lift weights, the physical weakness of his childhood fell away. When he left home and attended Harvard, he boxed, rowed and ran and, although he competed well, in the words of a contemporary, he “never took a championship.” Roosevelt was never the greatest in any of these things, but for him that was never the point. Each was about a chance to push himself to be better, believing that greatness lay on the other side of struggle. 

I have never in my life envied a human being who led an easy life; I have envied a great many people who led difficult lives and led them well.-Teddy Roosevelt

While Roosevelt was at Harvard, his father passed away and left him an inheritance of $125,000, making him the equivalent of a multi-millionaire in his time. But rather than choose a life of ease, Roosevelt push himself onward and went to Colombia to study law. It was there that the beginnings of his political life started.

A Rocky Start in Politics

Roosevelt began attending meetings of his local Republican Association, following a path that few people of his class would choose at that time. He soon ran for State Assemblyman in New York and beat the incumbent candidate and, upon winning, dropped out of law school and shifted his sights on political life, saying later on that he “intended to be one of the governing class.”

For several years, thing seemed to be going smoothly. Roosevelt began to make his mark in politics, serving in the New York State Assembly for several years, until 1884 when he would face the hardest day of his life. On Feb. 12, Roosevelt’s wife died two days after giving birth to their daughter—tragedy made only worse by the fact that his mother had died in the same house just hours earlier. 

His family gone, Roosevelt was facing a year of political struggle as well. His first steps onto the national political stage at the Republican convention were unsteady and ended poorly. He backed a candidate who lost and then lost the support of his own party when he switched allegiances. Without them, he was politically stranded.

Reinventing Himself in the West

So Roosevelt abandoned politics and did what he had his entire life in the face of struggle: Threw himself into the physical world. He struck westward with a dream of becoming a cattle rancher, building a ranch named Elkhorn. It was there where his reputation as a cowboy began, forever shaping his political image. He learned to ride and drive cattle, earning some respect from the local cowboys but—much as it was in his college days—never being the greatest; only dedicating himself to the effort, and his belief in the value of the righteousness of the struggle.

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood-Teddy Roosevelt

But hardship knew how to find Roosevelt in the West as well. In 1886, a bad winter wiped out his herd of cattle, along with a huge sum of his investment in the ranch. He returned to New York but found his luck wasn't much better there. When asked by Republican leaders to run for mayor, he came in third in the election and thought his political career was over.

Then, in 1986, Roosevelt began a political relationship with someone who would change the course of his life forever: William McKinley. Roosevelt had stumped for McKinley and was appointed Assistant Secretary of the Navy in 1897—a role most would be happy to have, but which Roosevelt resigned when the Spanish American War broke out. He wanted to fight and pursued it in spite of the objections of others.

Becoming a Legend

Roosevelt helped to form the First United States Volunteer Cavalry Regiment, later known as the Rough Riders. It was a group of men as diverse and unexpected as Roosevelt himself, made up of Ivy Leaguers and athletes, miners and hunters. Together they fought in Cuba and became famous for a charge on Kettle Hill in 1898, which Roosevelt called “the great day of my life.” 

After the war, Roosevelt was asked to run for office again—this time for Governor of New York—and finally his political luck started to change. He won. By the end of his term, people were talking about him as a possible presidential candidate, but Roosevelt had no desire to run against 
William McKinley, who would become the party's nominee. Then tragedy struck again—twice—but Roosevelt was finally on the right side of it.

In 1899, Vice Presidential candidate Garret Hobart died of a heart attack, and Roosevelt reluctantly accepted a nomination at his party's convention. He was one heartbeat away from the presidency when McKinley won election, and after serving a quiet six months as Vice President, on Sept. 6, 1901 President McKinley was shot. And six days later, he died.


The Unexpected President

Suddenly, the weak boy who sat up at night fighting for breath, too sick to play with others, became the most powerful man in the country. And once he had the power, the vigor Roosevelt had spent his life developing was set loose. He broke up railroad monopolies, ensured the construction of the Panama Canal and added huge tracts of lands to the national parks system out of his abiding love for nature. Even once out of office, he never stopped striving, attempting several more runs at the presidency in his later years.

Roosevelt refused to let anything stop him in life. When the stars aligned, that determination made great things possible, but his approach never changed while waiting for the winds to turn his way.

Nothing could sum that up better than when he was shot in the chest before giving a speech at a campaign rally in Milwaukee in 1912. Rather than being rushed to the hospital, Roosevelt took to the stage and delivered the speech anyway. He spoke for an hour and a half with the bullet still in his chest. His aides were nervous, but he never was. In his own words, “It takes more than that to kill a bull moose.”