Teddy Roosevelt: Accidental and Inevitable President

We take a look at Theodore "Teddy" Roosevelt, one of the most compelling figures in American history.  

Transcript

Accidental President Series: Teddy Roosevelt, the Inevitable Accidental 

February 2026

This section is longer than normal because, being a prolific writer, Roosevelt was a quote machine.  

“When we thus rule ourselves, we have the responsibilities of sovereigns, not of subjects.” 

“Speak softly and carry a big stick; you will go far.”

“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; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming.”

“Courage is not having the strength to go on; it is going on when you don’t have the strength.”

Historians, history buffs, and even non-historically minded Americans love “Teddy” Roosevelt. What’s not to love?  A scion of a fabulously wealthy old Dutch New York City family, he would go on to become a frontiersman, soldier, explorer, New York City Police Commissioner, Assistant Secretary of the Navy, Vice President, Conservationist, and President.  Roosevelt is one of those American characters who, if Leon Czolgosz’s (Chowl – Gaash) bullet had not propelled him to the White House, we would probably still know of him.  Even the name.  Almost every president since Lincoln has the telltale middle initial inserted.  It is not Rutherford Hayes or Richard Nixon; no, Rutherford B. Hayes and Richard M. Nixon, so as not to confuse us with all the other Richard Nixons.  Not so with Teddy.  I pride myself on presidential knowledge, but unlike his fifth cousin Franklin (middle name Delano), I do not conjure a middle name for him, since he did not have one.  The Roosevelts were so wealthy that they did not even need that moniker.  

And Teddy.  There is no Georgie, Tommie, or Franky in our history.  But Theodore has become Teddy.  He even has a stuffed animal named after him.    

And I call this the accidental president series.  In my previous podcast on Harry S Truman, I noted his selection as VP was no accident, because the Democratic powers and FDR himself knew he was dying.  But think of all the others, ranging from Tyler to Fillmore to Arthur to Ford.  Would any of these men have obtained the white house on their own?  Certainly not Fillmore or Arthur, and probably not Ford.  

Teddy Roosevelt was different.  Had McKinley lived, I would have zero doubt that in 1904 Teddy would have run for president and, given his persona, would have easily won in his own right, as he did that same year.  For me, Teddy is both accidental and inevitable.  

All of this is because, of course, Theodore Roosevelt stands as one of the most dynamic and transformative figures in United States history. Serving as the 26th president from 1901 to 1909, Roosevelt reshaped the presidency, expanded the power of the federal government, and redefined America’s role on the world stage. 

Known for his boundless energy, intellectual curiosity, and uncompromising moral vision, Roosevelt embodied the ideals of progressivism and national strength during a period of rapid industrialization and global change. His life—from a frail, asthmatic child to a rugged outdoorsman and forceful political leader—mirrored the broader American belief in self-improvement, civic duty, and national purpose.

Roosevelt was born on October 27, 1858, in New York City to a wealthy and socially prominent family. Despite his privileged upbringing, his childhood was marked by severe asthma and physical weakness. Rather than allowing illness to define him, Roosevelt adopted what he later called “the strenuous life,” a philosophy of discipline, physical exertion, and moral effort. 

Encouraged by his father, Theodore Roosevelt Sr., whom he and his siblings referred to as “Great Heart,”  the younger Theodore pursued exercise, boxing, and outdoor activity as a means of overcoming his limitations. The death of his father, when Teddy was just 19, caused deep, months-long grief.  His father was his role model and a close mentor. This trauma, occurring just before he met his first wife, solidified his “strenuous life” philosophy to overcome adversity. 

Roosevelt was an exceptionally curious and intelligent child, developing an early fascination with natural history, biology, and exploration. He attended Harvard University, where he studied history and government while continuing to cultivate his interest in science and literature. After graduating in 1880, Roosevelt briefly attended Columbia Law School but soon abandoned law for politics.

Entering politics at a young age, winning an election to the New York State Assembly in 1881 at just twenty-three, he gained a reputation as a reformer willing to challenge corruption within his own party. His early career was shaped by a commitment to honesty in government, efficiency in administration, and resistance to entrenched political machines.  I try not to pay a pop psychologist here, but growing up in a life of privilege, Teddy was never as tempted by wealth accumulation as others, which made it easy for him to challenge corruption in a way a poor kid might have struggled.  

Personal tragedy struck Roosevelt in 1884 when his wife, Alice Hathaway Lee, and his mother both died on the same day. Grief-stricken, Roosevelt temporarily withdrew from politics and retreated to the Badlands of North Dakota, where he ranched, hunted, and immersed himself in frontier life.  We will talk further about how Roosevelt transformed the presidency in political ways, but the first 100 years, except Jackson, of course, featured presidents who believed in exhibiting a rather stoical nature.  Not TR, he carried his emotions on his sleeves.  He was not the first to experience such tragedy, as politicians from Tyler to Pierce experienced personal loss.  But to abandon his native New York in an emotional crisis was relatively new.  

This period reinforced his belief in rugged individualism and the moral value of hard physical labor, themes that would later define his political rhetoric.

Roosevelt eventually returned to public service, holding several important positions that expanded his national profile. He served on the U.S. Civil Service Commission, where he aggressively enforced merit-based appointments and challenged the patronage system. Later, as president of the New York City Police Board, he pushed for professionalism, discipline, and accountability within the force.

In 1897, President William McKinley appointed Roosevelt Assistant Secretary of the Navy. In this role, Roosevelt advocated for naval expansion and preparedness, believing that a strong navy was essential to national security and international influence. Like many of his contemporaries, Roosevelt read Alfred Thayer Mahan, but he went further.  He deeply influenced him, considering The Influence of Sea Power upon History one of the most important naval books of the era. Roosevelt wrote a glowing review of Mahan’s work in 1890 and maintained a correspondence with him, adopting Mahan’s theories to justify expanding the U.S. Navy and building a canal. 

When the Spanish-American War broke out in 1898, Roosevelt resigned his post to serve in combat. He catapulted to national fame as the leader of the Rough Riders, a volunteer cavalry regiment that gained renown for its charge up San Juan Hill in Cuba.

In 1900, Roosevelt was elected vice president under William McKinley. I love this part.  Party leaders viewed the vice presidency as a way to sideline Roosevelt, whose reformist zeal made political bosses uneasy. This calculation proved short-lived. In September 1901, the aforementioned Leon Czolgosz assassinated President McKinley, and Roosevelt, at forty-two years old, became the youngest president in American history, a title he holds to this day.  Technically, John F Kennedy is the youngest to have been inaugurated, but because of Czolgosz, TR became president right away.  

Roosevelt approached the presidency with a strong sense of moral responsibility. He believed the president was a steward of the public interest, empowered to act decisively on behalf of the nation unless explicitly restricted by the Constitution. This “stewardship theory” marked a significant expansion of executive authority and permanently altered expectations of presidential leadership. One of the greatest exemplars of Roosevelt’s view of the office was his issuance of 1,081 executive orders.  We live in an era in which imperialistic presidents try to end-run Congress, and that body lets them, with executive orders.  But Roosevelt not only issued more executive orders than any previous president, but he also issued more than all 25 presidents before him COMBINED.  For example, he issued 10 times as many as his immediate predecessor, McKinley.  

A key Roosevelt term was the “bully pulpit” used to describe the presidency as a superb (“bully”) platform (“pulpit”) for advocating his agenda directly to the public. He used this position to influence public opinion, pressure Congress, and promote Progressive reforms such as antitrust laws and conservation, transforming the presidency into a powerful tool for shaping national policy. 

At the center of Roosevelt’s domestic agenda was the Square Deal, a program designed to ensure fairness between business, labor, and consumers. Yup, all the “deals” that we have seen and endured were started by Teddy.  The New Deal, the Fair Deal, heck, even the Green New Deal come straight from Teddy’s active mind.  

Roosevelt did not oppose capitalism; rather, he sought to regulate it in the public interest. He believed that large corporations, if left unchecked, could undermine democracy and economic fairness.

Roosevelt gained national attention for his handling of the 1902 coal strike, in which he intervened on behalf of the public to prevent a national energy crisis. Rather than automatically siding with business, Roosevelt acted as a neutral mediator, signaling a new federal role in labor disputes.

He also became known as a “trust-buster,” enforcing the 1890 Sherman Antitrust Act against monopolies that abused their power. While Roosevelt personally distinguished between “good” and “bad” trusts, his actions demonstrated that even the largest corporations were subject to federal oversight. Complementing these efforts were consumer protection measures, including the Pure Food and Drug Act and the Meat Inspection Act, both passed in 1906 in response to public outrage over unsafe industrial practices. Part of this was in response to The Jungle, a work by Upton Sinclair that exposed the horrific, unsanitary conditions in America’s meatpacking industry, revealing diseased meat, rodent contamination, and exploitative labor, which shocked the public.  

One of Roosevelt’s most enduring legacies is his commitment to conservation. An avid naturalist and outdoorsman, he believed that America’s natural resources should be managed responsibly for future generations. As president, Roosevelt dramatically expanded federal protection of land, establishing national parks, national forests, wildlife refuges, and monuments.

Working closely with conservationists such as Gifford Pinchot, Roosevelt promoted scientific management of resources rather than unregulated exploitation. By the end of his presidency, millions of acres had been placed under federal protection, laying the foundation for modern environmental policy and permanently altering the relationship between the federal government and the natural world.

Roosevelt’s foreign policy was guided by the belief that the United States should play an active and assertive role in global affairs. He famously summarized this approach with the phrase “speak softly and carry a big stick.” Roosevelt sought to avoid war when possible but believed that military strength was essential to diplomacy.

In Latin America, Roosevelt expanded the Monroe Doctrine through what became known as the Roosevelt Corollary, asserting the United States’ right to intervene in the affairs of Western Hemisphere nations to maintain stability and prevent European involvement. This policy increased American influence but also generated resentment and controversy.

Roosevelt also oversaw the construction of the Panama Canal, a monumental engineering project that enhanced global trade and solidified U.S. strategic power. His role in negotiating the end of the Russo-Japanese War earned him the Nobel Peace Prize in 1906, making him the first American to receive the honor.

After leaving the presidency in 1909, Roosevelt embarked on a series of adventures, including a dangerous expedition in Africa and later exploration of the Amazon River. He remained deeply engaged in politics, however, and grew frustrated with what he viewed as the conservative direction of his successor, William Howard Taft.

In 1912, Roosevelt broke with the Republican Party and ran for president as the Progressive Party candidate, commonly known as the Bull Moose Party.  This comes to a singular question: Do you like Woodrow Wilson?  From McKinley’s election in 1896 to Hoover’s landslide in 1928, the Republicans held dominance over the presidency, with the singular exception of 1912 and Wilson’s reelection, with World War I as a backdrop.  I have little doubt that had Teddy not run, Taft would have won easily, and there would have been no Woodrow Wilson.  

Although he lost the election to Woodrow Wilson, Roosevelt’s campaign introduced ambitious reforms, including women’s suffrage, social insurance, and stronger business regulation. The campaign demonstrated Roosevelt’s enduring influence and his willingness to challenge political norms in pursuit of reform.

Theodore Roosevelt died on January 6, 1919, at the age of sixty. Though not young by the standards of the day, it was not considered ripe old age either. 

Roosevelt’s legacy lies not only in specific policies but in the transformation of the presidency itself. He redefined executive power.  I have mentioned the executive orders and consider that, of the 25 presidents before him, they included Andrew Jackson and Lincoln, who fought the Civil War.  So when we see Barack Obama governing by Pen and Phone or Donald Trump ignoring Congress, there is a direct line back to Teddy.   

Historian Doris Kearns Goodwin, in describing Teddy for her book, Bully Pulpit, stated, “Rather than leading the country, he had a sensitive barometer to where the country was headed.”  I agree with this in part, but without his unique personality and unquestionably massive ego, I am not certain he would have done as much as he did.  A joke about Roosevelt was that “at every wedding he wanted to be the bride and at every funeral, the corpse.” 

Roosevelt was a great reader, “My reading was always a kind of living,” he explained later, “a longing to know some man or men stronger, braver, wiser, wittier, more amusing, or more desperately wicked, than I was, whom I could come to know well and sometimes be friends with.” But he was also a prolific writer with nearly 40 books to his name.  Kearns Goodwin attributes his unique facility with words to this fact.  

In his biography of Teddy Louis Auchincloss notes, “what survives in the panorama of history, even more than Trust busting or the Panama Canal or the ending of the Japanese Russo war is the vision of the asthmatic youth who made himself a he man, frontiersman, rough rider who charged up San Jaun Hill, wielder of the big stick who his sent his great white fleet around the world.”  More than any figure aside from Washington, the myth maketh the man.  

And that leads to other chroniclers of Teddy, such as Jim Powell in his Bully Boy: The Truth About Theodore Roosevelt’s Legacy, who condemn him.  Powell contends that instead of breaking up monopolies, he ensured their continuation.  That his conservatism had the opposite effect.  And for those concerned about an overmighty executive, only Wilson and FDR stand above.  

And women’s rights? “I am more and more convinced that the great field, the indispensable field for the usefulness of women, is the mother of the family. It is her work in the household.” Granted, this was not exactly seen as misogyny or anti feminism in 1906.  But it was the same year that Roosevelt died when the 19th Amendment, giving women the vote, was passed.  

I have so many mixed emotions about Theodore Roosevelt. I think he was a great man but something about his presidency, his life was misunderstood. In a Republic governed by separated powers, he believed that he was uniquely and specially qualified to govern others’ lives, a truly progressive conceit.  But what is missed is he wanted others to think as he did.  To strive not be ruled by Teddy, but to be a Theodore Roosevelt in their own rights.  

Yet he arrived at the juncture through his own individual accomplishments, not the least of which was turning a frail boy into a vigorous man.  

“It is the doer of deeds who actually counts in the battle for life, and not the man who looks on and says how the fight ought to be fought.”

One of his greatest legacies was that Roosevelt exemplified the belief in active citizenship, moral responsibility, and the idea that individuals—and nations—should constantly strive toward improvement. His life remains a powerful testament to the enduring influence of leadership rooted in energy, principle, accountability, responsibility, and purpose.  

Many admirers of Roosevelt liken him to Trump but Roosevelt would not have seen it.  Trump wants you to admire him.  And though there was certainly that aspect to Teddy (what president is averse to that sentiment) I believe he wanted people to admire themselves just as much.  Teddy wanted a nation of Teddys, not one Teddy and a thousand admirers.  And he was capable of self scrutiny in a way recent presidents from Obama to Biden to Trump seem incapable.  

“If you could kick the person in the pants responsible for most of your trouble, you wouldn’t sit for a month.”

For me, Roosevelt the individual man is a role model regardless of what you thought of the politician.