Ever looked at a dime and then at a picture of a guy screaming "Bully!" while charging up a hill in Cuba and wondered if they shared more than just a famous last name? It’s a classic trivia question that trips people up. Most assume they were father and son. Or maybe brothers. Honestly, the real answer is a bit more tangled than a simple family tree branch.
Are Teddy Roosevelt and Franklin Roosevelt related? Yes. But if you’re looking for a close-knit, Sunday-dinner type of sibling bond, you’re going to be disappointed. They were fifth cousins. That sounds distant, right? In modern terms, you probably don’t even know who your fifth cousins are. You might pass them in a grocery store and never blink. But for the Roosevelts, that thin thread of DNA was a highway to power.
The Roosevelt family was essentially a New York dynasty. They didn’t just live in the state; they practically owned chunks of it. Everything traces back to Claes Maartenszen van Rosenvelt, a Dutch immigrant who landed in New Amsterdam (now Manhattan) back in the mid-1600s. From him, the tree split into two very distinct, very wealthy branches: the "Oyster Bay" Roosevelts and the "Hyde Park" Roosevelts.
The Family Split: Oyster Bay vs. Hyde Park
The divide started with Claes's grandsons. Johannes Roosevelt stayed in New York City and eventually his descendants settled in Oyster Bay, Long Island. This was Teddy’s crew. They were Republicans. They were loud. They were "New Money" in spirit even if they had plenty of old cash.
Then you had Jacobus Roosevelt. His side of the family headed up the Hudson River to Hyde Park. These were the Democrats. They were perceived as slightly more aristocratic, though Teddy’s side would certainly have argued that point over a glass of sherry. FDR came from this line.
It’s weird to think about now, but these two men—the two most influential presidents of the 20th century—represented two different worlds despite that shared surname. They grew up in different circles, attended different social functions, and held radically different views on the role of government, at least initially.
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Enter Eleanor: The Bridge Between the Two Presidents
If you think the fifth-cousin thing is a bit far removed, wait until you hear about Eleanor. This is where the story gets really "small world."
Eleanor Roosevelt was Teddy Roosevelt’s favorite niece. She was an Oyster Bay Roosevelt by birth. When she married Franklin in 1905, she didn't even have to change her last name. Talk about convenient branding. Teddy actually walked Eleanor down the aisle because her own father, Elliott (Teddy’s brother), had passed away.
Imagine being at that wedding. You’ve got the sitting President of the United States—the most famous man on the planet at the time—stealing the spotlight from the groom. Teddy reportedly told Franklin, "Well, Franklin, there's nothing like keeping the name in the family."
This marriage changed everything. It turned a distant genealogical connection into a political powerhouse. It fused the two branches back together. Without Eleanor, it’s highly unlikely that Franklin would have had the same "in" with the political legacy that Teddy had built. He idolized his "Uncle Ted." He mimicked his career path: New York State Assembly, Assistant Secretary of the Navy, Governor of New York, and finally, the White House.
Comparison of the Two Icons
Despite the bloodline, they were polar opposites in personality. Teddy was a caffeinated whirlwind. He boxed in the White House until he lost sight in one eye. He hunted lions. He spoke with a high-pitched, staccato enthusiasm. He was the "Rough Rider."
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Franklin was different. He was suave. He was a creature of charm and deliberate calculation. Even before polio paralyzed his legs in 1921, FDR was seen as a bit of a "featherweight" by some of the hardened Oyster Bay clan. They thought he was a bit of a playboy. Teddy’s daughter, the legendary Alice Roosevelt Longworth, famously poked fun at Franklin for years. She was fiercely loyal to her father’s Republican legacy and viewed Franklin’s Democratic "New Deal" as a betrayal of the family name.
Alice once said of Franklin, "He was the kind of boy you invited to the dance, but not the kind you married." She was biting, hilarious, and deeply partisan. The rivalry between the Oyster Bay and Hyde Park Roosevelts wasn't just about politics; it was about who truly owned the "Roosevelt" brand.
Did They Actually Like Each Other?
It's complicated.
Franklin worshipped Teddy’s public persona. He basically used Teddy’s life as a blueprint. When FDR was a young man, he would visit Oyster Bay and soak up the energy. But as Franklin rose in the Democratic party, the relationship chilled. Teddy’s sons, particularly Ted Jr., were active in Republican politics and saw Franklin as a direct threat.
During the 1920s and 30s, the "Oyster Bay" Roosevelts campaigned heavily against Franklin. They didn't want the public thinking that the "Great TR" would have approved of the "Socialist" New Deal. There was a genuine sense of family betrayal. To the Oyster Bay group, Franklin was a "maverick" in the worst sense of the word.
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Yet, you can’t deny the influence. When FDR gave his first inaugural address, he was using a rhetorical style that echoed Teddy’s "Bully Pulpit." Both men believed the President should be the center of American life. They both believed in conservation (TR started the National Parks; FDR started the Civilian Conservation Corps). They both believed in a strong Navy.
Why the Connection Matters Today
Understanding that Teddy Roosevelt and Franklin Roosevelt were related helps us understand the 20th century. It wasn't just a coincidence that two guys with the same name became president. It was a testament to the power of American dynasties.
We often think of the U.S. as a place where anyone can grow up to be president. And while that's true in theory, the Roosevelt story shows how much a name, a network, and a legacy can move the needle.
- The Power of Mentorship: Even though they were distant cousins, Franklin’s obsession with Teddy’s career path gave him a roadmap that most politicians lack.
- The Complexity of Legacy: Family names can be a burden. FDR had to fight the "Oyster Bay" side of his family to define his own version of what it meant to be a Roosevelt.
- The Evolution of Parties: Seeing a Republican Roosevelt and a Democrat Roosevelt highlights how much our political parties have shifted their identities over 150 years.
If you want to dive deeper into this, I highly recommend reading The Roosevelts: An Intimate History by Geoffrey C. Ward or watching the Ken Burns documentary of the same name. It’s a wild ride through a family that basically treated the United States like a family business—sometimes for better, sometimes for worse.
Next time you see a 1900s political cartoon of a guy with big glasses and a mustache, or a photo of a man in a cape sitting by a fireplace for a "fireside chat," remember: they were cousins. Fifth cousins, sure. But in the world of power, that’s more than enough.
To really grasp the nuance, look at the 1912 election where Teddy ran as a third-party candidate. It fractured the GOP and paved the way for the future of the Democratic party that Franklin would eventually lead. The DNA might have been diluted by five generations, but the ambition was pure, concentrated Roosevelt.
Actionable Insights for History Buffs:
- Visit the Sites: To feel the divide, visit Sagamore Hill in Oyster Bay (TR's home) and then head up to Springwood in Hyde Park (FDR's home). The architectural and atmospheric differences tell the story better than any book.
- Trace Your Own "Fifth Cousins": Use a service like Ancestry or 23andMe to see how far a "fifth cousin" connection actually goes. You'll realize just how impressive it was that these two stayed in the same social and political orbit.
- Read the Letters: Look up the correspondence between Eleanor and "Uncle Ted." It reveals the genuine affection that existed before the political divide deepened.