Presidential Comparisons to Donald Trump: Teddy Roosevelt

Presidential Comparisons to Donald Trump: Teddy Roosevelt

In the previous installment, I compared our new President, Donald Trump, to former President Ronald Reagan, pointing out how both had rather unconventional backgrounds in show business prior to politics, campaigned on optimistic anti-establishment messages, and share a number of more superficial similarities such as setting age records and having amazing hair.

Now, for Part II, I shall compare Trump to another Republican President whom I find to be even more similar than Ronald Reagan, especially on policy specifics.

Part II: Theodore “Teddy” Roosevelt

Teddy Roosevelt is another individual whom Trump supporters would probably love to compare their man to. After all, Teddy is repeatedly ranked among the top 5 greatest presidents in American history, for both political and personal reasons.

Personal Upbringing

Perhaps more so than any other past president, Roosevelt and Trump share many striking similarities in their upbringings. Both men were born in New York City, to fathers who were businessmen and both had strong influences on their sons. Although they were both born into financially well-off and stable families, they both had massive ambitions – Roosevelt with his desire to go into politics, and Trump with his desire to expand the family business from Queens to Manhattan. Both of them built off of their families’ initial success to become even bigger.

Larger-Than-Life Personalities and Raw Patriotism

Right off the bat, there’s the simple but important comparison that both men crafted images of themselves as “macho,” or “alpha” males: Large, loud, tough, and bigger-than-life. They both used these images to heighten the perception that they alone were champions for American patriotism, and thus coupled their masculinity with the broader, nationalist message that they alone could restore American confidence and pride. Their core campaign messages are all-too similar: Teddy’s platform in 1912 was called “New Nationalism,” while Trump’s campaign slogan was “Make America Great Again.” Both invoked American pride, building off the glory of the past while also looking toward the future.

Political Incorrectness

In conjunction with the masculinity that both men share, there’s also another very infamous trait that they have in common: blunt talk and insults. Trump has made political incorrectness and direct insults of his opponents one of his key appeals, from slapping on nicknames to opponents (“Lyin’ Ted,” “Crooked Hillary,” “Little Marco,” and “Low-Energy Jeb”), to the regular uses of words such as “stupid,” “loser,” and “morons.” He has butted heads with publications such as the National Review, the New York Times, and TV channels. With his targets ranging from fellow candidates to the media, no one is off-limits for Trump.

Although the standard for political correctness has significantly changed in the 100+ years since Roosevelt’s time, it is worth noting that some of his own jabs at his opponents and critics were quite shocking for his day. He once called author Henry James “a little emasculated mass of inanity,” and boldly derided his predecessor, William McKinley, as having “no more backbone than a chocolate éclair.” He derided Woodrow Wilson as “a Byzantine logothete backed by flubdugs and mollycoddles,” and contemptuously slammed Benjamin Harrison as “a cold-blooded, narrow-minded, prejudiced, obstinate, timid old psalm-singing Indianapolis politician.” With all of these being public, Roosevelt was not afraid to make clear his exact distastes for anyone who crossed him. If he were alive today, he probably wouldn’t be afraid of direct expletives that would make even Trump blush.


Both men are among the most prominent populist figures in American history. In Teddy Roosevelt’s historic third-party run in 1912, his “Bull Moose Party” supported, among many other populist/progressive positions, a number of causes that moved some republican processes towards direct democracies, including: the direct election of U.S. Senators; recall elections of incumbent politicians; direct popular referendums on certain issues; popular votes having the power to override judicial rulings; and women’s suffrage. Trump has championed a whole new type of populism in the form of economic protectionism, opposition to free trade and globalist/multinational institutions, and curbing of dangerous or illegal immigration. This is in addition to a handful of other populist stances that mirror the ones Roosevelt held including: a proposed constitutional amendment imposing term limits on Congress, a variety of bans on lobbyists, a ban on foreign political donations, and a handful of other propositions. As a result of these forms of populism (among other factors), both men easily earned a strong disapproval from the political establishment of the time – which both men were all too eager to reciprocate.

Another major similarity between the two was their message of reaching out to and standing up for “the little guy.” With Teddy’s “Square Deal,” he promised to give economic opportunity back to average Americans through consumer protection and reigning in of big corporations. Trump similarly promises to help the average American with his “Contract with the American Voter,” promising to bring back blue-collar, working-class jobs from overseas through his economic protectionism, and fighting against special interests and the political elite.


Perhaps the one single issue where both men align the most is on the subject of immigration. As we all know, Trump has made immigration perhaps the central issue of his campaign. The liberal media’s narrative has been that Trump is simply against all immigration, but this is simply not true. Trump is firmly against illegal immigration, or mass immigration of groups that may be inherently incompatible with American culture (i.e., radical Muslims). But he is also firmly in favor of legal immigration of those who are ready to assimilate. From the significant legal immigrants who influenced his life (such as his mother and his wife), to his declaration that legal immigration is “what made America great,” he is able to paint his stances on immigration as a very black-and-white issue, and one that ties back to his overall patriotic theme.

What few may remember is that Teddy Roosevelt also held very similar views on immigration. He believed that all immigrants to the U.S. had to be “Americanize[d] in every way, in speech, in political ideas and principles, and in their way of looking at relations between church and state…no other flag should even come second.” This rhetoric would indeed align with Trump’s idea that immigrants to the U.S. must accept American culture and assimilate with it, and that immigrants from inherently rival cultures would not be welcome. Similarly, Roosevelt famously said that “we cannot have too much immigration of the right sort, and we should have none whatsoever of the wrong sort,” and that when it came to vetting of immigrants, the only factor that should be looked at is “that man’s fitness for citizenship…the individual quality of the individual man.” Thus, not only did Teddy Roosevelt propose the strictest idealistic standards on immigration, but he justified such ideas with the association of pride and American culture.

Progressive Republicans

Trump and Teddy were definitely more progressive/liberal than the rest of the Republican Party at the respective times of their rises, often differing with party leadership on the issues that contributed to their populism: Teddy supported workers’ compensation, a sort of “National Health Service,” and the earliest kind of “social insurance,” while Trump supports broad acceptance of the LGBTQ community, raising taxes on the wealthy (including even himself), and opposes significant cuts to social welfare programs such as Social Security and Medicare.


Despite all their similarities, one crucial difference remains between Teddy Roosevelt and Trump: Trump succeeded in winning the nomination of a major party. Roosevelt, in 1912, formed his own candidacy when he was rejected by the Republican Party. As such, only one of these two men was successful in their presidential bids. Nevertheless, there is no doubt that Trump’s historic election is just as much of an upset to the political system as Teddy’s third-party candidacy would have been had he won. Therefore, President Trump could help paint a faint picture of what it may have looked like had Teddy Roosevelt won in 1912.

You can follow the author on Twitter: @EricLendrum26

The Next Move: Using the Constitution to Save the Constitution, Part III

The Next Move: Using the Constitution to Save the Constitution, Part III

Trump Won Because of Bigotry

Trump Won Because of Bigotry