History likes to bundle people into neat little boxes. We see the name Roosevelt and we think of a singular, monolithic American dynasty that basically ran the 20th century. But if you actually dig into the FDR and Theodore Roosevelt related history, it’s way messier than that. It’s a story of awkward family dinners, massive political betrayals, and a weird sort of hero worship that changed the country forever.
They weren't brothers. Not even close. Teddy was Franklin’s fifth cousin.
That didn't stop Franklin from basically stalking Teddy’s career path like a blueprint. TR was the Republican firebrand, the "Rough Rider" who became President in 1901. FDR was the Democrat who looked at that legacy and said, "Yeah, I'll have what he's having." It created this bizarre dynamic where the two most influential Presidents of the last 150 years were essentially operating out of the same playbook but on opposite teams.
The Family Tree Is More Like a Web
People always ask how they were actually related. It’s a bit of a brain teaser. Theodore was from the Oyster Bay wing of the family—the Republicans. Franklin was from the Hyde Park wing—the Democrats. They were fifth cousins, which, in most families, means you might see each other at a funeral once every twenty years and forget each other's names.
But it gets weirder.
Franklin married Eleanor Roosevelt. Eleanor was Theodore’s favorite niece. She was a Roosevelt by birth. When she married Franklin in 1905, Theodore actually walked her down the aisle because her own father, Elliott (TR’s brother), had passed away. Imagine being at that wedding. The sitting President of the United States steals the show at your nuptials, cracking jokes and drawing every eye in the room. Franklin didn't mind. He idolized the man.
Actually, idolized might be an understatement. Franklin followed TR’s path with a precision that borders on spooky. TR was in the New York State Assembly; so was Franklin. TR was Assistant Secretary of the Navy; so was Franklin. TR was Governor of New York; so was Franklin. It’s like Franklin was wearing a "What Would Teddy Do?" bracelet for thirty years.
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The Republican Roosevelts Hated the Democratic Ones
You might think the family would be proud to have two presidents. Think again. The "Oyster Bay" Roosevelts—Theodore’s kids and their cousins—eventually grew to despise Franklin. They saw him as a "maverick" in the worst sense, or worse, a traitor to his class.
Alice Roosevelt Longworth, TR’s daughter and the reigning queen of D.C. sass, famously said Franklin was "one-third sloppiness and two-thirds Eleanor." Ouch.
The rift was real. When FDR started implementing the New Deal, the Republican side of the family viewed it as a radical departure from the "Square Deal" that Theodore had championed. They felt Franklin was using the Roosevelt name to push "socialist" agendas that TR would have hated. Was that true? It's debatable. Theodore was the original trust-buster. He was the one who decided the government should have a say in how big business treats people. Franklin just took that seed and grew a whole forest.
Policy DNA: From the Square Deal to the New Deal
If you look at the FDR and Theodore Roosevelt related policy shifts, the DNA is obvious. Theodore gave us the "Square Deal." He wanted a fair shake for the average worker, conservation of natural resources, and consumer protection.
Then comes 1932. The Great Depression is eating the world alive.
Franklin steps up and offers the "New Deal." It wasn't just a catchy name; it was a direct linguistic nod to his cousin’s legacy. He took Theodore's concept of the "Stewardship Theory"—the idea that the President can do anything not explicitly forbidden by the Constitution to help the public—and pushed it to the absolute limit.
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Why the Comparison Matters Today
- Expansion of Power: Both men fundamentally changed the office of the Presidency from a purely administrative role to a "bully pulpit" (TR’s phrase) of moral and social leadership.
- Environmentalism: TR started the National Parks. FDR started the Civilian Conservation Corps (CCC), which built the infrastructure for those parks.
- Media Savvy: TR used the newspapers and "muckrakers." FDR used the radio for his "Fireside Chats." Both understood that you can't lead if the people aren't listening.
The Polio Factor and the "Soft" Roosevelt
Before 1921, many in the family thought Franklin was a bit of a lightweight. He was handsome, charming, and maybe a little too eager to please. Theodore was the guy who got shot in the chest and finished his speech anyway. Franklin was the "pretty boy" from Hyde Park.
Then polio hit.
The struggle to regain even a modicum of mobility changed Franklin. It gave him a grit that mirrored Theodore’s physical toughness but in a quieter, more empathetic way. It’s honestly one of the most significant pivots in American history. Without that struggle, Franklin might have remained a pale imitation of his cousin. Instead, he became his own version of a "Strong Man," leading the country through its two greatest 20th-century crises: the Depression and World War II.
What Most People Get Wrong About the Rivalry
The biggest misconception is that they were close friends or that TR mentored Franklin. They weren't. TR died in 1919, long before Franklin became a national powerhouse. Their "relationship" was mostly one-sided, with Franklin studying TR like a textbook.
Also, we tend to forget how much Theodore’s own sons resented Franklin’s rise. Ted Jr. and Kermit Roosevelt were trying to make their own marks in politics and the military. Seeing their "Democratic cousin" swoop in and take the ultimate prize—using their father’s rhetorical tricks—had to sting. It was a family feud played out on the front pages of the New York Times.
Practical Takeaways for History Buffs
If you're trying to understand how the American government became the massive entity it is today, you have to look at these two. You can't just study one.
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1. Trace the Lineage of Executive Orders
Look at how TR used executive power to create national monuments. Then, look at how FDR used it to create the WPA. It’s the same muscle being flexed, just 30 years apart.
2. Visit the Sites
To really get it, you have to see the difference in their homes. Sagamore Hill (TR’s house) is a rugged, cluttered man-cave of trophies and books. Springwood (FDR’s home) is a refined, stately manor. The houses tell the story of their personalities: the impulsive hunter versus the calculating strategist.
3. Read the Letters
The correspondence between Eleanor and "Uncle Ted" is gold. It shows a softer side of the Rough Rider and explains why Eleanor, more than anyone else, was the bridge between these two eras of American progressivism.
The Roosevelt era didn't just happen by accident. It was a 50-year project where one man’s charisma provided the spark, and his cousin’s ambition provided the engine. They were two sides of the same coin—a coin that, for better or worse, bought the modern American state.
To dig deeper into this legacy, start by reading The Roosevelts: An Intimate History by Geoffrey C. Ward or watching the Ken Burns documentary of the same name. These sources break down the complex psychological ties that bound the Hyde Park and Oyster Bay families together. Next, compare TR's 1912 "New Nationalism" speech with FDR's first inaugural address; you will see the exact moment the torch was passed between the two versions of American liberalism.