By Cara Lombardo
Activist investor Carl Icahn says nothing compares to the thrill of being immersed in a fight.
For the past few years, the 89-year-old billionaire has been playing defense on several fronts.
He is trying to revive the fortunes of Icahn Enterprises, the publicly traded company that houses his investments, after a 2023 short-seller attack shaved billions off its market value and his own net worth. But a relationship with one member of the investing team recently turned contentious. And he feels it has become next to impossible for activists to wage the types of shareholder fights he loves and that have made him a fortune.
On the home front, as he nears his 90th birthday, he's faced recent health scares and has separated from his wife of over 25 years, costing him a steady ally.
Icahn remains his combative self, publicly denying he's concerned about any of it and focused on what he sees as momentum.
"I keep going," he said in one of several interviews over the past month. "I enjoy the game."
He describes the third-quarter earnings his firm reported Wednesday as some of its "best ever," and he plans to unveil two new investments soon. He is obsessed with a pet project focused on removing voting power from index funds, which he believes could restore activists' bite.
Shares in Icahn Enterprises, known by its ticker IEP, are down roughly 80% from before the short seller arrived. Hindenburg Research, now defunct, had alleged IEP was overvalued and vulnerable from its founder borrowing against its shares.
Forbes estimates that Icahn's net worth is now closer to $4.5 billion, down from above $17 billion years a few years ago.
"They took part of my army away, like Alexander the Great," Icahn said of the attack, which dented his capacity to make new investments. "He has to change his battle plans, but it's not that bad."
Icahn likes to point out that the IEP stock continued paying annualized dividends of $2 a share throughout the ordeal.
IEP reported net income of $287 million in its third quarter, up from $22 million a year ago, confirming earlier reporting from The Wall Street Journal.
The value of IEP's investments, its net asset value, rose to $3.8 billion, up $567 million since June 30, primarily due to CVR Energy, a small refiner it controls. The increase would have been even higher, if not for short positions Icahn has long maintained as a hedge.
Soon, IEP will reveal a big stake in automotive service chain Monro, people familiar with the matter said. IEP, which holds board seats on seven public companies excluding those it controls, is also in talks to join the board of another company, the people said.
An empire in transition
Inside IEP, succession remains murky, some recent hires have soured and blockbuster wins have been missing.
Brett Icahn, Carl's son, officially rejoined the firm in October 2020, signing a seven-year contract to lead a team of three investors he hired.
One of that team's ideas, a big bet on Bausch Health, has lost the firm an estimated $760 million, according to data-provider Old Well Labs.
Of the three investors, one left last year and the firm's relationship with another, Steven Miller, recently became contentious, according to people familiar with the matter.
The third, Andrew Teno, was named chief executive officer of IEP early last year and is seen as the most likely person to carry on the firm's operations should the elder Icahn die.
Brett is expected to succeed his father as chairman and run the firm's investment unit. He is rarely seen in IEP's Miami-area office and devotes some of his time to personal investments. He is engaged to his longtime girlfriend with plans to elope.
The 46-year-old did have a hand in a recent home-run investment in EchoStar, the satellite-and-wireless company chaired by Charlie Ergen, according to people familiar with the matter. The bet made IEP over $250 million in one week earlier this year.
Changes at home
Icahn has separated from Gail, his second wife and former assistant, whom he married in 1999.
The two had disagreements over money and he voided parts of their prenuptial agreement, according to people familiar with the matter. They also had diverging lifestyles, with Gail preferring to socialize and travel and Icahn preferring to stay home and work.
Gail, 76, remains chairman of Icahn's charter schools and the two still spend time together.
Icahn has been dealing with a string of health issues. Surgery to remove a skin issue near his ankle made it painful to walk for roughly a year and forced him to give up daily tennis.
Not long after the surgery, he was getting dressed to go to a party at real-estate investor Steven Roth's Hamptons estate when he scraped the wound. Blood began rushing out, covering the floor.
"I sort of gave in and said, 'This might be it for me,'" Icahn said. "I relaxed."
It ended up to be a result of his blood-thinner medication and the issue quickly resolved.
Soon after, he was treated for an enlarged spleen . The initial dosage of medication made him short of breath, making it hard to work and talk on the phone at his normal pace. His doctors have since adjusted it. He says he never missed a day of work.
After spending the summer in the Hamptons, Icahn is wintering at his house on the Miami-area island known as Billionaire Bunker. His neighbors include Tom Brady and Jeff Bezos, though Icahn rarely socializes or goes to the island's exclusive club.
Two male assistants take turns spending the night and fixing his evening martinis. He works many days from a patio table overlooking Miami's Intracoastal Waterway. He has been reading Theodore Dreiser novels including "The Titan," part of a trilogy about a ruthless businessman.
He bets on NFL games every week. On Sunday, he won around $80,000 with bets on the San Francisco 49ers and the Seattle Seahawks.
A new crusade
Icahn says he is devoting much of his energy to targeting index funds' voting rights. He is finishing a white paper on the topic, with the help of ChatGPT queries run by staffers.
He rails against what he calls the "cartel" of BlackRock, Vanguard and State Street, though is just as likely to shorthand them all by naming BlackRock CEO Larry Fink.
The way Icahn sees it, with index funds controlling around 30% of most companies' voting rights, it has become impossible for activist investors to run proxy fights for control of corporate boards. He argues such fights are good for the overall economy, but rarely win support from the index funds.
BlackRock and its peers say they are giving some investors voting powers and otherwise carefully determine votes delegated to them to maximize investors' financial interests. They also point to legal issues that currently prevent them from giving all investors the ability to vote their own shares.
Icahn wants either Congress to act or President Trump to issue an executive order. One proposal from Republican lawmakers would require shares held in passively managed funds to be voted on a proportional basis according to instructions from fund investors. Icahn has shied away from politics since he was accused of using a short-lived role in Trump's first term to his advantage but plans to agitate on this issue.
Icahn is tending to his legacy elsewhere too. He recently put his New York City penthouse back on the market for $23 million after struggling to unload it since moving to Florida in 2018. He says the performance of the Icahn School of Medicine at Mount Sinai, funded with $200 million in 2012, makes it his best investment ever. And he is focusing on charities that prevent dogs from being euthanized.
Write to Cara Lombardo at cara.lombardo@wsj.com
(END) Dow Jones Newswires
November 05, 2025 08:48 ET (13:48 GMT)
Copyright (c) 2025 Dow Jones & Company, Inc.
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