How Theodore Roosevelt Built His Reputation

By the time he became President of the United States at the age of 42, Theodore Roosevelt had already been a celebrity for decades. How did someone so young maintain such fame (which waxed and waned with the seasons, but remained at a baseline throughout)? He came from a family that was well-known in New York, which helped launch his career, but that doesn’t explain his rise to the forefront of the national consciousness. In The Rise of Theodore Roosevelt, we see other factors at work, aside from his raw charisma and force of personality, which deserves an entry on its own.

Here’s what we learn from his early career and his rise to power.

1. Maintain your independence and focus on popular causes

When assessing Julius Caesar’s leadership style in my old post “11 Lessons in Leadership from Julius Caesar,” we saw that he constantly associated himself with the causes of reform which were popular among the Roman people. This was not merely for the sake of his own ambition. He understood that the balance of power within Roman society had been severely disrupted by its rise to hegemonic status and that reforms were needed to stabilize it. He chose to ally himself with these efforts and against the “best men” in the Roman Senate, who tried to block them. He was unafraid of attacking people far more powerful than him. It helped his reputation and got him the attention he needed to make a name for himself.

Like Caesar, Theodore Roosevelt came from an aristocratic family, but also like Caesar, he spent his time with all kinds of different people, spanning the various social classes and sectors of society. He was just as comfortable, perhaps even more so, with backwoodsmen in Maine and cowboys out west as he was at elite balls in his own backyard. This gave him a broad perspective on the whole American society.

He wasn’t yet known as a trust buster in those early days. He didn’t speak out against the robber barons at this point in his career, though privately in the aftermath of the 1896 election, he expressed his disdain for the attempt by Mark Hanna to join the Republican Party at the hip with big business. Much earlier, though, Theodore Roosevelt committed himself to rooting out corruption within the Republican Party machine and in government.

In service of that cause, he would often lead independent-minded Republicans, who skewed younger, on reform causes, withholding their support and using it as leverage against the party machines to at least get part of what they wanted. The best example of this came in the 1884 Republican National Convention, though the effort ultimately failed.

Throughout his career, Theodore Roosevelt made an effort to side himself with a fair balance of power and always opposed to corruption, even if it sometimes hurt him. He often attacked powerful figures and dragged them onto the battlefields he wanted to fight on, enhancing his reputation in the process, which brings us to the next attribute of his rise.

2. Be consistent and lack bashfulness

In How to Fail at Almost Everything and Still Win Big, Scott Adams describes overcoming shyness as a skill. Theodore Roosevelt had a natural talent in this. Bashfulness was not a word in his vocabulary. This allowed him to apply his principles consistently. One example from his early career came when he was the Republican Party leader in the New York State Assembly. Governor Grover Cleveland had just vetoed a popular municipal reform bill on grounds that it was poorly thought out and inconsistent, even if the end goal was desirable. His reasoning actually proved popular with the people and he won praise for his bravery.

Theodore Roosevelt, who was the leading champion of the bill, publicly praised Cleveland’s veto and bucked members of his own party in Albany for raising their ire at it. This damaged his standing in the party and aided the machine in ousting him as the party leader in the next legislative session, but his reputation as a true independent who could not be put into a box by machine interests found itself enhanced for the long term.

The biggest example of his consistency, though, was when he enlisted to fight in the Spanish-American War, resigning from his cushy job as Assistant Secretary of the Navy to do so. Peers pointed out that he had basically designed the naval strategy for the war and he would do better staying on in that role. He replied that he had always talked of going to the front and as he had done much to bring on the war, he had to fight in it. The result was the glory of San Juan Hill in Cuba, which was entirely consistent with his stances.

Theodore Roosevelt San Juan Hill Cuba

His reputation came not only through his bold actions and decisions, but through how he sold them and the consistency which he lived by them, which brings us to the next item.

3. Maintain energy, frame, and press management

Edmund Morris calls Theodore Roosevelt the greatest virtuoso of press relations of the 19th century. This was because he understood how the press operates. Much like Donald Trump in The Art of the Deal, he knew that the press is more interested in stories that will get attention rather than in any specific devotion to “the truth.” So he thought that he may as well get the press to pay attention to the stories he wanted them to. Theodore Roosevelt used his energy and his causes to sell stories, becoming a box office draw. The press knew he sold, so they liked covering him.

He knew that the way to sell was to pick a fight. He sold his stories by keeping with his persona as a youthful, independent Republican fighting machine corruption and calling out the misbehavior of powerful officials. This was how a Civil Service Commissioner – an otherwise little-known bureaucrat – got national attention by taking on the Postmaster General (then a cabinet-level office). He did this by investigating post office irregularities and inviting witnesses to testify on the biggest platform he could give – to make the story more prominent. Civil service reform was a popular cause and he dominated the space of the movement as its ardent champion, always framing himself as being the right party against the corrupt machine. His enemies helped in this process, as they often tried backroom deals to stop his efforts. When word got out, he looked better, because it reinforced the frame he had set.

You can read much more in The Rise of Theodore Roosevelt by Edmund Morris. The full review will go up next week.

Theodore Roosevelt also features prominently in Lives of the Luminaries. He has the longest chapter in the book. Click here to take a look.

And if you liked this post, hire me.

Support me on Patreon and find out the one simple behavior that will make you more productive without feeling exhausted.