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Donald Trump Thinks He’s a Modern Teddy Roosevelt. I Hope He’s Right in 2024

If he runs for president again, the future of the US will depend on it.

Jeremy Helligar
5 min readFeb 18, 2021
Theodore Roosevelt, left, and Donald Trump (Photos: flickr and Gage Skidmore/Wikimedia Commons)

Donald Trump’s second impeachment trial didn’t yield the results some of us wanted, but this story might still have a happy ending. Even if he doesn’t end up in an orange jumpsuit or spend years tied up in criminal and/or civil courts, too mired in litigation to run for president again, he could follow in the footsteps of the former commander-in-chief he admires most.

When Trump looks in the mirror, he sees a modern-day Andrew Jackson and a 21st century Teddy Roosevelt, images many of his fans see as well. For Trump, apparently, either would do — but the latter carries more contemporary weight. He’s even dreamed of carving out a new niche alongside the 26th US president on Mount Rushmore. Both comparisons, especially the TR one, reveal how little Trump and many of his disciples know about US history.

A famously progressive Republican (back when the party more closely resembled the Republican Party of Abraham Lincoln), Roosevelt would have despised pretty much everything Trump and the modern Republican Party stand for. Frail and sickly as a child, TR, who, like Trump, benefitted from inherited wealth, willed himself into the masculine ideal so valued by 45.

He was a self-made alpha male who became a celebrated war hero, the leader of the Rough Riders during the Spanish-American War. Roosevelt once delivered an entire speech while bleeding from a would-be assassin’s bullet, and he probably would have mocked Trump’s using bone spurs as an excuse for sitting out the Vietnam War.

So why the comparisons? Policy and general level of bravery have nothing to do with it, but here’s where the two heirs intersect: Roosevelt described the presidency as a “bully pulpit,” and that’s precisely how Trump used it, with an emphasis on “bully.”

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Jeremy Helligar
Jeremy Helligar

Written by Jeremy Helligar

Brother Son Husband Friend Loner Minimalist World Traveler. Author of “Is It True What They Say About Black Men?” and “Storms in Africa” https://rb.gy/3mthoj

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