He wasn't your typical spy. When you think of the CIA in the fifties, you probably picture a sleek, Bond-style operative, but Kermit "Kim" Roosevelt Jr. looked more like a soft-spoken academic. He was the grandson of Teddy Roosevelt. He had that Ivy League air about him. Yet, in 1953, this man basically carried a million dollars in a suitcase into Tehran and flipped a country upside down. The relationship between Kermit Roosevelt and Iran is one of those historical pivots that sounds like a fever dream, but it set the stage for almost every Middle Eastern headache the US has faced since.
It’s wild.
Most people think of the 1953 coup—Operation Ajax—as this massive, monolithic military machine rolling through the streets. It wasn't. It was messy. It almost failed twice. At the center of it was Kim Roosevelt, sitting in a safe house, ignoring orders from Washington to give up and come home. He was a gambler.
The Man Who Ignored His Bosses
By the time 1953 rolled around, Iran was in a state of absolute chaos. The Prime Minister, Mohammad Mosaddegh, had done the unthinkable: he nationalized the oil industry. Before this, the Anglo-Iranian Oil Company (now BP) basically owned the place. The British were furious. They tried a blockade. They tried legal threats. Nothing worked. So, they turned to the Americans.
Enter Kermit Roosevelt.
He didn't just walk in and start shooting. That's not how it worked. Roosevelt understood that power in Tehran was about optics and the "street." He spent weeks coordinating with local contacts, bribing newspaper editors, and organizing "protestors" who were basically hired muscle. It was psychological warfare. He needed to make it look like the Iranian people hated Mosaddegh, even though the guy was actually pretty popular for standing up to the West.
Interestingly, when the first attempt at the coup flopped on August 15, the CIA station in Washington sent Roosevelt a telegram. They told him to get out. They said the operation was a failure and he needed to save himself.
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He stayed.
He literally hid in the basement of a CIA house, ignored the "abort" mission orders, and decided to double down. That’s the kind of ego we’re talking about here. He was convinced he knew the local landscape better than the bureaucrats back in D.C. Honestly, he was right, at least in the short term. He used his remaining cash to hire a mob that included everyone from weightlifters to professional rioters to create the illusion of a popular uprising.
Why the Oil Crisis Fueled the Fire
You can’t talk about Kermit Roosevelt and Iran without talking about the money. Specifically, the black gold. Mosaddegh wasn't a communist—he actually quite disliked the Soviets—but the British convinced President Eisenhower that he was a "red" threat.
The British logic was simple:
If we can't have the oil, nobody can.
Roosevelt played into this fear perfectly. He framed the intervention not as a corporate bailout for an oil company, but as a crusade for democracy and stability. It was a lie, obviously. The goal was to put the Shah, Mohammad Reza Pahlavi, back in absolute control. The Shah was terrified, though. He was so nervous he actually fled to Baghdad and then Rome during the heat of the operation. Roosevelt had to practically drag the monarchy back into power.
The "Rent-A-Crowd" Strategy
This is the part that feels like a movie script. Roosevelt realized that the Iranian military was divided. If he could create enough chaos in the streets, the military would feel "forced" to intervene to restore order.
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He hired a guy known as "Shaban the Brainless." No, seriously. Shaban Jafari was a local strongman and circus performer who led a gang of thugs. Roosevelt's team funneled money to these groups to attack pro-Mosaddegh rallies. Then, they hired another group to pretend to be pro-Mosaddegh communists and attack religious leaders.
The goal? Make the city look like it was falling apart so the "silent majority" would beg for the Shah to return.
It worked. By August 19, the streets of Tehran were a war zone. Mosaddegh’s house was leveled by tank fire. The Prime Minister surrendered, and the Shah flew back to Tehran to take his throne. Roosevelt met the Shah shortly after, and the Shah famously told him, "I owe my throne to God, my people, my army—and to you."
The Long-Term Fallout Most People Miss
We often look at 1953 as a "success" because it achieved the immediate goal. The oil started flowing again. The Soviets were kept out. But there’s a massive "but" here.
Kermit Roosevelt’s success created a blueprint for the CIA that was, in hindsight, pretty toxic. Because it was so "cheap" and "easy" to topple a government in Iran, the US thought they could do it everywhere. It led directly to the mess in Guatemala in 1954 and eventually the Bay of Pigs.
More importantly, it broke the trust of the Iranian people. They knew. They weren't stupid. They saw the American hand behind the Shah’s increasingly brutal secret police, the SAVAK. When the 1979 Revolution happened, the anger wasn't just at the Shah; it was at the ghost of Kermit Roosevelt. The hostage crisis at the US embassy wasn't a random event—it was a direct response to 1953. The protestors were terrified the US was going to pull another "Operation Ajax" and put the Shah back in power again.
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Debunking the Myths
There are a few things that get lost in the academic papers about this.
- Myth 1: It was all about Communism. While that was the "sell" to the public, Roosevelt’s diaries and later accounts suggest it was much more about regional influence and preserving the British-American alliance.
- Myth 2: Roosevelt acted alone. He was the architect, but he had massive help from British intelligence (MI6) and local Iranian elites who were losing money under Mosaddegh.
- Myth 3: The coup was inevitable. It wasn't. If Mosaddegh had been more aggressive in using the Tudeh (Communist) party for protection, or if the Shah had stayed in the country, the outcome could have been totally different.
Roosevelt later wrote a book called Countercoup. The CIA actually made him change a lot of it before publication because he was a little too honest about how much they manipulated the local press. He was proud of what he did. He saw it as a grand adventure.
What This Means for Today
Understanding Kermit Roosevelt and Iran isn't just a history lesson. It’s a case study in "blowback." When we look at the current geopolitical tension between Washington and Tehran, we are looking at the ripples of a stone thrown in 1953.
It reminds us that short-term tactical wins often lead to long-term strategic disasters. Roosevelt "won" the battle of 1953, but the US has been losing the war for Iranian hearts and minds ever since.
Actionable Insights for History Buffs and Analysts
If you want to really get the full picture of this era, don't just take one person's word for it. History is written by the winners, but the losers usually keep better notes.
- Read "All the Shah's Men" by Stephen Kinzer. It is widely considered the gold standard for understanding how the coup actually functioned on the ground. It uses declassified documents that Roosevelt tried to keep quiet.
- Look into the "Abadan Crisis." To understand why Mosaddegh was so angry, you have to look at the living conditions of the Iranian oil workers compared to the British executives. It makes the "villain" Mosaddegh look a lot more like a labor rights hero.
- Trace the SAVAK lineage. Research how the intelligence apparatus Roosevelt helped stabilize eventually became the tool of the Shah’s downfall.
- Evaluate modern interventionism. Compare the "Ajax" model to more recent attempts at regime change. You'll notice that the "propaganda and street money" tactic is still a primary tool, though it's much harder to hide in the age of the internet.
The story of Kim Roosevelt is a reminder that one person with a clear plan and a lack of oversight can change the trajectory of an entire region. Whether that change was for better or worse depends entirely on who you ask in the streets of Tehran today.
Next Steps for Deep Research
To see the primary evidence yourself, you should search the National Security Archive at George Washington University. They have the "Internal CIA History of the Service" which was leaked in 2000. It provides the most clinical, non-sensationalized account of Roosevelt's daily movements during the coup. Pay close attention to the memos regarding "Appendix B," which details the specific bribes paid to Iranian clergy members to turn them against Mosaddegh.