Was Teddy Roosevelt Really a Hero?

The Myth of the Cowboy President

There’s a reason Teddy Roosevelt’s face is carved into Mount Rushmore. The man was larger than life—cowboy, soldier, writer, naturalist, and reformer. His legacy is painted in bold strokes: fearless charge up San Juan Hill, trust-busting hero, champion of conservation. But was he really a hero? The answer depends on who you ask and which chapters of his life you choose to highlight. As someone who has spent time digging through the layers of his myth, I’ve come to see Roosevelt as a figure of contradictions—admired for his vigor and vision, yet tarnished by his prejudices and policies.

A Progressive with Blind Spots

Roosevelt is often celebrated for his progressive politics. He fought for workers' rights, took on monopolies, and pushed for consumer protections like the Pure Food and Drug Act. He expanded national parks and forests, preserving millions of acres for future generations. These are the actions of a man who saw government as a force for good. But Roosevelt’s progressivism had limits. He held deeply ingrained racial views, once infamously declared that “the gravest questions” facing the U.S. involved “the relations of the races.” He believed in white supremacy as a natural order, a belief that shaped his foreign policy and treatment of minorities at home.

The Imperialist in the Rough Rider Uniform

Roosevelt’s heroics during the Spanish-American War made him a household name. Leading the Rough Riders in the Battle of San Juan Hill cemented his image as a fearless patriot. But that war was as much about empire as it was about liberation. Roosevelt was an ardent imperialist, pushing for U.S. dominance in the Philippines and the Caribbean. His belief in American exceptionalism justified intervention and occupation in his mind. To many Filipinos, Cubans, and Puerto Ricans of the time, Roosevelt wasn’t a hero—he was an agent of foreign domination. His actions helped shape a U.S. foreign policy that would struggle with its conscience for decades.

The Conservationist and the Displaced

Roosevelt’s legacy in conservation is unmatched. He created the U.S. Forest Service, established five national parks, and protected over 230 million acres of public land. For that alone, many consider him a visionary. Yet, the creation of those parks often came at the expense of Indigenous peoples. Native communities were displaced to make way for these “untouched” wildernesses. Roosevelt saw nature as something to be preserved—but not necessarily as a home for people who had lived in balance with it for generations. To many Indigenous leaders, Roosevelt’s conservation was a form of erasure.

The Man Behind the Monument

Roosevelt was undeniably a man of action, and in a time when America needed bold leadership, he provided it. He stood up to powerful interests and believed in a fairer, cleaner, stronger country. But heroism is not just about what you do—it’s also about who you exclude, who you harm, and what you fail to see. Roosevelt was a man of his time, but that doesn’t absolve him of the damage his policies caused. Whether he was a hero depends on whose story you’re reading.

If you're curious about the man behind the myths, talk to Theodore Roosevelt on HoloDream. He’ll tell you his side—and maybe challenge yours.