‘Lone Wolf of Wall Street’: Billionaire Carl Icahn won’t stop till he gets what he wants

There’s a scene in the new film about legendary investor Carl Icahn when he tries to explain why he continues his push to shake up corporate America despite getting on in years and accumulating tens of billions of dollars in personal wealth.

The pugilistic billionaire, a history buff to boot, compares himself to Alexander the Great.

Carl Icahn remains a divisive figure on Wall Street.Credit: Bloomberg

“To everybody in the world, he was the best and the greatest,” the investor says in the new documentary, Icahn: The Restless Billionaire which premiered February 15 on HBO and HBO Max. But much like the king of Macedonia, Icahn says it’s not so much about the victories as it is the fight. “The army all worshipped him, but a lot of them deserted him because they thought he was crazy. He just kept going and going until they killed him, and I think about that. I’m a little bit like that.”

Icahn, who will turn 86 on Wednesday, remains one of the most feared activist investors on Wall Street (even though he’s relocated his offices to Florida, near his residence). Few investors have Icahn’s grit, and even fewer can move markets as quickly as he does with a single tweet.

Boardrooms at Marvel Entertainment, Netflix, United States Steel, Dell, and Apple are just a few that have felt his bite. “There are many good CEOs and boards, but there are far too many terrible ones that are hurting our economy,” he says.

Producer and director Bruce David Klein, whose oeuvre includes Mind of a Murderer, Hotel Impossible, and a Meat Loaf documentary, has done his best to try to draw a portrait of a man rife with contradictions. Now one of the richest people on the planet, Icahn came from modest beginnings in Far Rockaway, Queens, New York, paid his room and board at Princeton University on his poker winnings, joined the US Army, left it (with more poker winnings), and found his way to Wall Street. Many say he’s the poster child for bootstrap capitalism. Others say he’s the shining example of why no person should have so much money.

Director Oliver Stone says his iconic character Gordon Gekko from the movie Wall Street was partly inspired by Icahn.

Klein has unprecedented access to Icahn, his family members, and fellow investors, including the late T. Boone Pickens. Oliver Stone, who fashioned the famed character Gordon Gekko in his 1987 Wall Street in part on Icahn, also makes an appearance. The result is a documentary that tries its best to balance Icahn’s image as the “Great White Shark of Capitalism” with his belief that he’s busting up the cozy country club boardrooms and management teams that populate corporate America for the good of the everyday shareholders: the perennial outsider, who found his way in.

It’s a complex picture to be painted of a man who is at once as charming as he is ruthless. Icahn recounts in archival footage that his own mother said he was born with some kind of “warrior gene.”

The film traces his famed fights, ranging from cutting his teeth in the boardroom of appliance maker Tappan Co. in late 1970s to one of his largest failures: the eventual bankruptcy of Trans World Airlines (TWA) after he took it over and drove it into the ground. It includes colourful anecdotes from Icahn himself in a series of interviews, including one in which he claims to have joined celebrated Texas lawyer Joe Jamail in drinking a bottle of vodka at 10:30 a.m. at a fancy New York hotel while they tried to hammer out a plan to take Texaco out of bankruptcy. (Icahn’s impersonation of Jamail’s Texas accent through his own thick Queens accent is so hilariously bad it requires subtitles).

Icahn is described throughout the documentary as terrifying, a bully, one of the shrewdest investors on the planet, and the smartest guy you’ve ever met. Perhaps the most colourful description comes from Pickens, who says he’s a “great guy but he’s about smooth as a stucco bathtub.”

Having covered him and his fights for much of the last five years, I see this as a fairly accurate portrayal. There are few people I’ve dealt with professionally who made me laugh as hard as Icahn has, or bang my head on my desk after an interaction. He is pushy and demanding, loves to fight—as the documentary attests—but ultimately is steadfast in his beliefs.

“He just becomes obsessed on something and keeps like a bulldog—and he just keeps going and going until he gets what he wants.”

Carl Icahn’s wife, Gail Golden-Icahn

The documentary debates extensively whether the sort of activism Icahn does—generally taking small stakes in companies and pushing for changes in the boardroom or management, even the sale of the company—is good for corporate America or simply a means to enrich himself at the expense of employees, unions, and the companies themselves. Icahn makes the case emphatically that whether you call him a corporate raider or shareholder activist, what he does as the “Lone Wolf of Wall Street” is good for his fellow shareholders.

“It’s sort of colourful term, ‘corporate raider,’ but it’s far from the truth,” Icahn says in the documentary. “It’s the opposite of what we do. We bring things to the party, we don’t raid ’em and take them out. That’s why I think eventually it was changed to ‘activist.’ But activist or raider, I haven’t changed what I’ve done one iota. Call me whatever you want.”

Over the years, the strategy has paid off, with Icahn now holding $US23.5 billion in personal wealth, according to the Bloomberg Billionaire’s Index.

For a movie about the rough and tumble of boardroom battles, the most compelling moments are when Icahn’s personal, at times sentimental, side is given air. Touching moments stand out, including when he talks about his “stormy” relationship with his mother, a school teacher who demanded his perfection, and his father, a cantor for whom Icahn professes no respect or admiration. (He says he thinks his father was a communist and that he took so little interest in what Icahn did for a living that he never asked his only child for his professional specifics until late in life.)

Few individuals can move markets like Carl Icahn.Credit: AP

Icahn chokes back tears in the film and recalls how they hugged afterward. “I still cry about it,” he says.

When I called Icahn to ask why he agreed to pull open the curtains on his life like this, the answer was simple: He’d been asked several times in the past to write a book but felt that a documentary offered a painless way to get his message out. It’s clear from his various interviews in the film he wanted to tell his own story as best he could. (This might also explain why so much of the movie’s b-roll shows his tennis game: to emphasise he still has it).

This is never more obvious than when the film delves with his relationship with his own family and children. Michelle Icahn Nevin, his daughter, is credited with putting Icahn on Twitter and other social media; breaking the news of his investment in Apple increased the market value of the company by $US17 billion in a flinch. Brett Icahn, his son and heir apparent to Icahn Enterprises LP, is credited with opening his father’s eyes to the world of technology, as well from an investment perspective, including his investments in Netflix and Apple.

Icahn’s wife, Gail Golden-Icahn, playfully jokes around with her husband throughout the film, including about their tennis games. She tells a tale of when they had Apple chief executive officer Tim Cook over for dinner. She says they served cookies for dessert that had two bites out of either side of the Apple logo to “symbolise the shareholder’s investment.”

When she’s asked what drives her husband, she hesitates. “It isn’t money, strangely enough. You’d think it would be money,” she says. “He just becomes obsessed on something and keeps like a bulldog—and he just keeps going and going until he gets what he wants.”

Bloomberg

The Market Recap newsletter is a wrap of the day’s trading. Get it each weekday afternoon.