You’ve seen the faces on the monuments. One is carved into a mountain in South Dakota with a mustache that looks like it could stop a train. The other is usually sitting in a wheelchair, cigarette holder tilted at a jaunty angle, looking like he just won a poker hand with a pair of twos.
Most people think of the Teddy Roosevelt and Franklin Roosevelt connection as just two guys with the same last name who lived in the White House. Maybe they’re brothers? Cousins? Honestly, it’s weirder than that. They were fifth cousins, sure, but they were also uncle and nephew-in-law. Eleanor Roosevelt was Teddy’s favorite niece. When she married Franklin in 1905, Teddy—the sitting President of the United States—walked her down the aisle. He literally gave the bride away to his own distant cousin.
It’s a tangled web.
But here is the thing: you cannot understand the 20th century, or even the polarized mess of 2026, without looking at how these two men redefined what a President actually does. They didn't just hold the office; they grabbed it by the lapels and shook it until the furniture moved.
The Bully Pulpit vs. The Fireside Chat
Teddy was the Republican who acted like a radical. Franklin was the Democrat who acted like a savior. Yet, they both used the same playbook.
Teddy coined the term "Bully Pulpit." For him, "bully" meant "excellent" or "wonderful"—kinda like how we might say something is "awesome" today. He realized that the President has a microphone that nobody else has. If he wanted to break up Standard Oil or save the Grand Canyon from being turned into a private mine, he didn't just wait for Congress. He went to the people. He shouted. He wrote books. He made himself the center of every story.
Then came FDR.
Franklin saw what Teddy did and smoothed it out. While Teddy was a loud, boisterous storm, Franklin was a calm, steady breeze. He invented the "Fireside Chat." During the Great Depression, people were literally starving. Banks were locking their doors. Franklin didn't shout. He sat in front of a microphone and spoke to Americans like they were sitting in his living room. He used the radio—the cutting-edge tech of the 1930s—to bypass the newspapers and talk directly to the voters.
It was the same strategy, just updated for a new medium.
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The Split in the Family Tree
You’d think the Roosevelts were one big happy family, but the "Oyster Bay" Roosevelts (Teddy’s side) and the "Hyde Park" Roosevelts (Franklin’s side) were often at each other’s throats. Teddy’s kids were openly annoyed when Franklin started his political ascent. They felt he was a bit of a "copycat."
Alice Roosevelt Longworth, Teddy’s daughter and a legendary DC wit, famously said of Franklin: "My father always wanted to be the corpse at every funeral, the bride at every wedding, and the baby at every christening." She didn't mean it as a compliment to Franklin; she meant that the Roosevelt ego was a hereditary trait that both men shared in spades.
How the Square Deal Became the New Deal
If you look at their policies, the Teddy Roosevelt and Franklin Roosevelt link becomes even tighter.
Teddy had the "Square Deal." He focused on the "three Cs":
- Conservation of natural resources.
- Control of corporations.
- Consumer protection.
He was the first "Trust Buster." He went after J.P. Morgan and the Northern Securities Company because he believed no corporation should be more powerful than the government. He was a Republican, but he hated "malefactors of great wealth." He wanted a fair shake for the little guy.
Thirty years later, the world fell apart. The stock market crashed in 1929, and by 1932, the country was desperate. Franklin took Teddy’s "Square Deal" and put it on steroids. He called it the "New Deal."
It wasn't just a catchy name. It was a massive expansion of the federal government that we are still arguing about today. Social Security? That’s FDR. The SEC (which regulates the stock market)? That’s FDR. Minimum wage? FDR. He took the "Control of Corporations" idea from Teddy and built an entire bureaucracy to manage it.
The Conservation Legacy
People forget that Teddy was a hunter who became the greatest conservationist in history. He set aside 230 million acres of public land. He established the United States Forest Service.
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Franklin followed suit during the Depression by creating the Civilian Conservation Corps (CCC). He put 3 million young men to work planting trees, building trails in National Parks, and fighting forest fires. It was a brilliant move—it solved unemployment while doubling down on Teddy’s environmental legacy. If you’ve ever hiked a trail in a state park and noticed a stone bridge or a sturdy cabin, there is a very high chance a "CCC boy" built it during the New Deal.
World Wars and Global Power
Both men were obsessed with the Navy.
Teddy was the Assistant Secretary of the Navy before he quit to lead the "Rough Riders" in Cuba. As President, he sent the "Great White Fleet"—a massive group of battleships—on a world tour just to show everyone that America had arrived as a global power. He won the Nobel Peace Prize for mediating the Russo-Japanese War, but he always carried a "big stick."
Franklin also served as Assistant Secretary of the Navy. (See the pattern?)
When World War II broke out, FDR didn't just want to defend America; he wanted to lead the world. He understood, perhaps better than anyone, that the "splendid isolation" Teddy’s generation flirted with was over. He helped draft the Atlantic Charter, which laid the groundwork for the United Nations.
They both moved America from a sleepy, inward-looking nation to the dominant global superpower.
The Physical Struggle
Here’s a detail that often gets glossed over in textbooks. Both Roosevelts had to overcome massive physical hurdles, which shaped their "tough guy" personas.
Teddy was a sickly, asthmatic kid. He was bullied. He was weak. He decided to "make his body," spending his life boxing, wrestling, and ranching in the Dakotas to prove he wasn't fragile. That "Strenuous Life" philosophy drove everything he did.
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Franklin had it even harder. In 1921, at age 39, he was struck by polio. He lost the use of his legs. For the rest of his life, he couldn't walk without heavy steel braces and someone's arm to lean on. But he never let the public see him as "weak." He made a secret pact with the press—they wouldn't photograph him in his wheelchair, and he would provide them with the best stories in town.
That shared grit is why they both felt they could take on the entire world. They had already beaten their own bodies.
Why Should You Care in 2026?
We live in an era where people are constantly debating the "reach" of the government.
When you hear politicians arguing about "Big Tech" monopolies today, they are literally using Teddy Roosevelt’s notes. When people talk about the "Green New Deal," they are explicitly referencing Franklin’s branding.
The Teddy Roosevelt and Franklin Roosevelt era ended 80 years ago, but the structure of our modern life—our national parks, our retirement system, our role as a global military power—is entirely their doing.
Real-World Takeaways
If you want to apply the Roosevelt mindset to your own life or business, here is how you do it:
- Adapt the Medium: Don't just do what everyone else is doing. Teddy used the tabloid press; FDR used the radio. If you're trying to reach people today, find the "fireside" equivalent for 2026—whether that's raw, unedited video or direct community engagement.
- The "And" Philosophy: You can be a conservationist and a hunter. You can be an aristocrat and a champion for the working class. Don't let labels box you in. Both Roosevelts were master "class traitors" who used their privilege to benefit those who had none.
- Energy Wins: Teddy’s "Vigor" and Franklin’s "Optimism" were their greatest weapons. In a crisis, the person who looks like they have a plan and the energy to execute it usually wins the room.
To really get the full picture of this dynasty, your next step should be to look into the 1912 Election. It was the only time a former President (Teddy) ran against a sitting President (Taft) and a future-shaping challenger (Wilson). It split the Republican party and essentially paved the emotional way for the New Deal.
After that, check out the Roosevelt Campobello International Park. It's the only park in the world owned by two different countries (US and Canada) and it’s where Franklin’s summer home was located. It’s a physical testament to the internationalist world he tried to build.