He sits in a sun-drenched room, leaning back like a man who has already won everything. But he hasn’t stopped. At 86, Carl Icahn is still hunting. Most people know him as the "Corporate Raider." Others call him an "Activist Investor." Honestly, the labels don't seem to matter much to him. He’s the subject of the HBO documentary Icahn: The Restless Billionaire, and if you’ve ever wondered how one man can move the entire stock market with a single tweet, this is the story you need to hear.
It’s about the "Icahn Lift." It's about a kid from Queens who played poker to pay for Princeton.
The documentary, directed by Bruce David Klein, isn't just a highlight reel of bank balances. It’s a look at the "Lone Wolf of Wall Street." You see a guy who ribs his wife, Gail, about her tennis game and then turns around to dismantle a Fortune 500 board. He’s complicated. He’s relentless. Basically, he’s the real-life inspiration for Gordon Gekko, though Icahn would probably tell you Gekko was too soft.
Why Icahn: The Restless Billionaire Still Matters
The film matters because the "Icahn era" never really ended. We’re living in it.
When Carl Icahn buys a stake in a company, CEOs start sweating. He doesn't just buy shares; he buys a seat at the table—or he kicks the table over. The documentary dives into his philosophy of "creative destruction." He finds companies that are fat, lazy, and poorly managed. Then, he strikes.
Take the 2013 Apple deal. Icahn took a massive position and started yelling—loudly—that Apple should buy back its own shares. The result? A $17 billion "Icahn Lift" in the stock’s value. It’s a pattern he’s repeated with Netflix, Marvel, and Texaco. But it isn't always pretty. Critics point to TWA (Trans World Airlines) as the dark side of his legacy. He took it private, sold off the routes, and the company eventually spiraled into bankruptcy while he walked away with millions.
Is he a hero for shareholders or a villain for employees? The movie doesn't really pick a side. It just lets Icahn talk.
The Poker Player from Queens
You’ve got to understand where he started to get why he's so restless. Icahn wasn't born with a silver spoon. He grew up in Far Rockaway, Queens. His parents were teachers, and his father was also a cantor. He was an only child who learned early on that if you want something, you have to outsmart the guy across from you.
At Princeton, he studied philosophy. Think about that for a second.
Most Wall Street titans study finance or MBA-speak. Icahn studied logic and the "Empiricist Criterion of Meaning." This gave him a weird edge. He doesn't see numbers; he sees human behavior and systemic flaws. He actually paid his way through school by winning at poker. He told the filmmakers that he studied the game so hard he became "instinctive" at reading people.
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He treats the stock market exactly like those poker games in the Army. "You look for something I call a 'no-brainer,'" he says in the film. "Very little risk, but a lot of reward."
The Activist vs. The Raider
There is a huge debate in the financial world about what Icahn actually does. In the 80s, the term was "greenmail." He’d buy enough stock to threaten a takeover, and the company would pay him a premium just to go away. It felt like a stick-up.
Icahn hates that term.
In Icahn: The Restless Billionaire, he argues he’s a "benevolent activist." He believes corporate America is run by "country club" CEOs who are overpaid and underperforming. By forcing them to change, he claims he’s helping every small shareholder. Bill Gates and Oliver Stone show up in the doc to provide context. Stone even admits that Icahn’s rants at shareholder meetings provided the "skeleton" for the "Greed is Good" speech in the movie Wall Street.
The Famous Feuds
If you like drama, the Herbalife section is pure gold. This was the legendary showdown between Icahn and Bill Ackman. Ackman bet $1 billion that Herbalife was a pyramid scheme and would go to zero. Icahn? He hated Ackman. He bought the stock just to squeeze him.
On live TV, Icahn called Ackman a "crybaby in the schoolyard" and a "major loser."
It wasn't just about the money. It was personal. That’s the "restless" part of the billionaire. He doesn't just want to win; he wants the other guy to lose. He eventually made a billion dollars on that trade, while Ackman walked away with his tail between his legs.
A Complicated Legacy
The film touches on his son, Brett Icahn, who is the heir apparent. Brett was the one who pushed his dad to invest in Netflix and Apple early on. It shows a softer side of Carl—a father trying to pass on a kingdom built on conflict.
But even with the family moments, you can’t ignore the "collateral damage." When Icahn "restructures" a company, people lose jobs. 12 floors of people, sometimes. He calls it "creative destruction." To the people on those 12 floors, it’s just destruction.
He’s also honest about his failures. TWA still "smarts," he says. He admits the system is "bad," and that’s why he’s able to make so much money. It’s a cynical view of capitalism, but coming from a guy with $20 billion, it’s hard to ignore.
What You Can Learn from Carl Icahn
You don't need a billion dollars to take something away from his story. His life is basically a masterclass in independent thinking.
- Go against the grain. Icahn says you have to buy things when the rest of the world thinks you're crazy. If everyone likes an investment, it’s probably too late.
- Do the numbers. He says "did the numbers" over and over. Before he gets emotional or aggressive, he ensures the math is bulletproof.
- Understand psychology. Because of his philosophy background, he knows that boards of directors act like herds. If you can break the herd, you can win the game.
- Never stop. The man is in his late 80s and still works every day. He’s not doing it for another yacht; he’s doing it because the "hunt" is the only thing that makes him feel alive.
The documentary ends with a bit of a chilling thought. Alexander the Great wept because there were no more worlds to conquer. Icahn seems to be looking for his next India. He’s still calling CEOs. He’s still tweeting. He’s still restless.
If you want to understand the modern economy, you have to understand the man who helped break it and rebuild it in his own image. Go watch the documentary on HBO or Max. It’s a 100-minute look into the mind of a shark who forgot how to stop swimming.
To dig deeper into his current moves, you should look up his latest 13F filings. These are public documents that show every stock he currently owns. It’s the closest thing to a roadmap of his mind. You might also want to compare his style to other "activists" like Nelson Peltz or Dan Loeb to see how the game has changed since the 80s.
Focus on the "Icahn Enterprises" (IEP) performance if you want to see how his personal holding company operates in real-time. It's the best way to track the "Restless Billionaire" today.