The Rise—and Fall—of Theodore Roosevelt
The most interesting man to ever be president is also a cautionary tale
Because I value my free time less than others, I just finished reading a three-part biography of Theodore Roosevelt by Edmund Morris. The first volume, The Rise of Theodore Roosevelt, won both the Pulitzer Prize for Biography and the National Book Award in Biography in 1980. The series is a monumental achievement of history and biography that chronicles the life of a man who was probably the most interesting man to ever become president of the U.S.
Roosevelt was born to a wealthy family in Manhattan just before the Civil War. One of his first memories was viewing the funeral procession of Abraham Lincoln pass below his balcony. Roosevelt was a sickly boy who suffered regular bouts of illness and debilitating asthma. But unlike other chronically ill people, he never succumbed to depression over the state of his body. Instead, he pushed himself hard as a child to overcome disease and to develop himself into a strong young man. Roosevelt was equally determined to learn anything he could about the world around him. To that end, he spent hours reading in his family library and exploring the outdoors. Poor vision helped him develop an acute sense of hearing, which he used to great effect to listen to and catalog the bird sounds he heard whenever he ventured into the woods.
His upbringing was both unusual and loving. Because his father was so wealthy, Roosevelt was able to travel extensively in Europe with his family. As a result, by the time Roosevelt became president, he had already been overseas something like three or four times, often spending long stretches of time in Europe. He was also partially educated in Germany by a family who appreciated his talents and pushed him to develop as a mature young thinker and writer. By all accounts, that education helped: Roosevelt studied for and passed the Harvard entrance examinations, despite receiving no formal education.
Toward the end of his years at Harvard, Roosevelt married one Alice Lee, and moved with her back to Manhattan, where he began attending classes at Columbia Law School. After class, Roosevelt walked across town to the library to research his first professional book, The Naval War of 1812. (Roosevelt had previously written a shorter, more amateurish book on birds.) The end result of this labor was a book that was considered to be the definitive history of the naval war in 1812 for the next century.
But despite having an aptitude for law, that profession was not in his future. He became interested in politics during his time at Columbia and developed a passion for civil service reform and good governance. Roosevelt detested the spoils system in which political bosses appointed friends or campaign donors to prestigious, cushy government jobs. He began speaking out about the issue and raised his profile to the point where he was elected New York Assemblyman for his district in Manhattan. During his second term in Albany, Roosevelt became the youngest-ever minority leader, which was the result of his adroit leadership of the Republican Party. Tragically, Roosevelt wasn’t able to celebrate for too long: His mother and wife both died on the same day after his wife gave birth to his daughter. Roosevelt didn’t deal well with grief. Instead of mourning her publicly, Roosevelt suppressed his feelings. The name “Alice Roosevelt,” according to Morris, was never uttered by Theodore again. It always pained him that his daughter was named after his wife, to the point where he often left her with his sister for long stretches of time and called her “Baby Lee” because he couldn’t bear to say the name Alice.
After a few terms in the New York State Assembly, Roosevelt grew tired of politics. He bought a ranch in the Dakota territory and spent months there at a time. But while other city slickers would have felt out of place in the West, Roosevelt fit right in. The only difference was his respect for the rule of law as opposed to good, old-fashioned frontier justice. In one memorable story, some men stole a canoe from Roosevelt’s property and paddled it downriver. After building a new canoe with his associates, Roosevelt pursued the men and eventually caught them. But instead of executing them on the spot, as most other cowboys might have done, Theodore brought his captors back to the closest town, which was miles away by foot. The sheriff was flummoxed.
Eventually, Roosevelt felt the call of public service—and matrimony—once more. After a failed run for mayor of New York in 1886, he was appointed by then-President Benjamin Harrison to the Civil Service Commission, where he fought the spoils system that he hated so much. Roosevelt later became New York City Police Commissioner, where he patrolled the streets and called out corrupt and inept cops. He then became Assistant Secretary of the Navy under William McKinley, where he pushed the U.S. toward greater naval preparedness and had a hand in launching the Spanish-American war in the face of Spanish aggression in the Philippines and Cuba. Roosevelt resigned from the Navy Department to enlist in the military. He became a decorated colonel, commanding a cavalry unit called the Rough Riders because it was made up of ranchers and other Westerners. Roosevelt was then elected governor of New York, where his crackdown on corruption and on corporations made Republican bosses wary. To get him out of the governor’s mansion in Albany, party bosses lobbied to get him appointed as William McKinley’s Vice President.
McKinley was assassinated shortly into his second term. Roosevelt took over as president and continued his crusades against corruption, the spoils system, monopolies, and corporate expansion into the vast forests and canyons of the American West. Roosevelt knew well how to use executive power, including the so-called “bully pulpit,” to sway public opinion toward his own policies and to get Congress to do his bidding. He achieved many successes over his two terms, including the recognition of Panama as an independent state and the construction of the Panama Canal. Roosevelt also set up dozens of national parks, forests, and even bird sanctuaries in his push for conservation. He was reelected by a wide margin in 1904 and promised not to run again.
But when he left office, Roosevelt became disappointed with his self-appointed successor, William Howard Taft. Taft seemed to capitulate to conservative Republicans rather than continue Theodore’s progressive legacy. After a two-year stint of travel in Africa and Europe, Roosevelt returned home as a candidate for the 1912 Republican nomination. He lost that race and started a new party, the Bull Moose or Progressive Party, and ran the most successful third-party campaign in the history of the U.S. Nevertheless, he lost, and returned to his home on Long Island.
The story of Roosevelt’s final years is mostly one of steady and sad decline. He went on an exhilarating river journey in Brazil, where he explored an unmapped river through the Amazon rainforest. But his health began failing him again, despite years of vigorous activity, and it never fully recovered. He also agitated to get the U.S. into World War I far before President Woodrow Wilson was comfortable doing so. When the war did begin, Roosevelt unsuccessfully petitioned Wilson’s War Department to send him to Europe as commander of a volunteer cavalry regiment. But his four sons did manage to enlist, and all of them became heroes. Unfortunately, this decoration came at a cost: Roosevelt’s youngest son, Quentin, died after being shot down by a German plane. Rooosevelt died in the early days of 1919 at the age of 60.
Theodore Roosevelt lived a remarkable life. He overcame crippling illnesses as a child to become a strong, healthy young man. He spent much of his professional career fighting for good governance and against corruption. And by all accounts, he was a good man. But he wasn’t perfect. Besides being a somewhat absent father to his eldest daughter Alice, Roosevelt was also a wannabe king—or whatever is closest to king in a democracy. Even though he promised to stick to the two-term tradition set by George Washington and ratified by every president after him, Roosevelt went back on his word and ran for a third term. It may seem like a technicality, since his first term was really a fulfillment of McKinley’s second. But Roosevelt himself recognized that he was functionally running for a third term. There was even talk of nominating Roosevelt as a Republican—he had reconciled his differences with the party that refused to nominate him in 1912—in 1920, but he died before history could determine the outcome of that contest.
As I was finishing the final book in Morris’s masterful biography, Colonel Roosevelt, I was thinking about the lessons we can learn from Theodore Roosevelt. There are many, but I’ll try to be brief. First, we should recognize the value of what Roosevelt called the Strenuous Life. Most Americans today are sedentary, which leads to all sorts of poor health outcomes. We would do well to get outside more often and exercise.
Second, we should respect Roosevelt’s crusade for good governance and against corruption. We live in a time where more politicians are more focused on ginning up outrage about the policies and rhetoric of the other side than on making the government work for the people. Meanwhile, the IRS is manually entering tax returns sent by mail rather than relying on computers for such rote data entry tasks. Talk of corruption is too tied up in current political dramas for it to apply as well here, but at the very least, we should all push back against Senators caught with gold bars given to them by foreign governments as bribes.
Finally, Roosevelt is a prime example of a man who peaked too early and couldn’t let go of his yearning for glory. We should be wary of these types of men (and women). Roosevelt became president at 42, the youngest ever to do so. As a result, he retired from the highest office in the land before 50. He was never truly happy during his retirement and always wanted to return to the White House. This meant that he spent much of his time agitating against his successors and remaining in the public eye. His pondering of a 1920 run, cut short by his premature death, is worrisome. If he had survived until that time and won, he would have been either a president or president-in-waiting for at least 25 years. That would be like Bill Clinton running for president now and winning again—but, during the intervening decades, writing incendiary columns and hating on Bush, Obama, Trump, and Biden. Roosevelt was unable to retreat into obscurity after a breathtaking rise to power. We should recoil against men like him who refuse to step aside and observe.
Actually, there’s one thing I want to leave readers with. In many ways, Roosevelt is a terrifying figure. He was charismatic, influential, and adept at wielding power. This made him formidable as a candidate. As a result, it’s likely that he would have become a quasi-dictator like his cousin-nephew Franklin (it’s a weird family tree). Still, I think more Americans should aspire to be like Theodore. Whatever his faults, he was an interesting person—and a good one. His mind was as sharp as his muscles were hard, and his life experiences were almost unbelievable. Moreover, he was an effective politician who knew how to get things done. If today’s politicians were more like Theodore Roosevelt, perhaps we’d be in a better position than we are in now.
Won a Nobel Prize, climbed the Matterhorn, skinny dipped in the Potomac - while President. Yes, I'd say he was an interesting fellow :)