The most feared investor on Wall Street

Carl Icahn is one of the most feared and influential figures on Wall Street. For decades, he has made billions by forcing struggling companies to restructure, ousting CEOs, and pressuring firms into major stock buybacks. Some see him as a ruthless corporate raider, while others view him as a force that keeps executives accountable.

This week, we explore how Carl Icahn built his fortune, the strategies that made him one of the most feared investors, and the corporate battles that defined his career.

• 💼 From Poker to Wall Street

• 💥 The Art of Hostile Takeovers

• ⚔️ Battles With CEOs and Wall Street Feuds

— Investor Briefcase Team

Carl Icahn grew up in Queens, New York, and was expected to pursue a traditional career path. He attended Princeton University, where he studied philosophy before enrolling in New York University’s medical school. However, after three years, he decided medicine was not for him and dropped out.

Instead, he turned to professional poker. By the late 1950s, Icahn was playing high-stakes games, using the winnings to fund his early investments on the stock market.

After realizing that he would need a more stable career path, he took a job as a stockbroker at Dreyfus & Co. in 1961, where he quickly gained a reputation for aggressive trading. By 1968, he secured a $400,000 loan from his uncle and used it to purchase a seat on the New York Stock Exchange. That same year, he decided to launch his own firm, Icahn & Co., specializing in options trading and arbitrage.

His early years were spent identifying undervalued companies and trading them for quick profits. But he soon realized that owning companies and influencing their decisions was far more lucrative than simply trading stocks. By the late 1970s, he shifted his focus to corporate takeovers, an approach that would make him one of the most powerful figures in finance.

Icahn’s investment strategy is built on control and pressure. He buys a large stake in a company and demands changes, pushing executives to cut costs, sell assets, or return cash to investors. If management refuses, he wages a proxy battle, rallying shareholders to replace leadership with those who will follow his vision.

His first major hostile takeover came in 1985 with Trans World Airlines. Icahn gained control, took the company private, and stripped it for cash. The deal made him hundreds of millions, but the airline was left drowning in debt and eventually collapsed. The move solidified his reputation as one of Wall Street’s most aggressive corporate raiders, a title he welcomed as he went on to target some of the biggest companies in the world.

Over time, Icahn refined his approach. Instead of outright takeovers, he used his influence to push companies into stock buybacks. In 2013, he targeted Apple, arguing it was hoarding cash. His pressure led to a $100 billion stock buyback, boosting its stock price and adding billions to his portfolio.

Not every move worked. His attempt to force a sale of Xerox failed, and bets in retail and energy led to losses. But his influence changed corporate America. Many firms now adopt shareholder-friendly policies just to keep him away.

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One of the most dramatic battles in Wall Street history was Icahn vs. Bill Ackman over Herbalife. In 2012, Ackman publicly bet $1 billion against the company, calling it a pyramid scheme. Icahn took the opposite position, buying a large stake and defending Herbalife.

The feud became personal, with both billionaires attacking each other on live television. Icahn continued increasing his stake and pushing for share buybacks, while Ackman doubled down on his short bet. After years of public clashes, Ackman conceded defeat in 2018, closing his short position with massive losses. Meanwhile, Icahn cashed out with over $1 billion in profits.

Icahn’s activist approach has kept companies accountable and reshaped corporate strategy. Even at 87, he remains a force in the markets, proving that no company is beyond the reach of shareholder pressure.

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Other Feared Investors Like Carl Icahn

> Paul Singer: Founder of Elliott Management, Singer is known for his aggressive activist investing tactics, often targeting struggling companies and sovereign debt. His firm has been involved in high-profile battles, including forcing Argentina into a costly debt settlement and shaking up major corporations like AT&T and Twitter.

> Daniel Loeb: Founder of Third Point LLC, Loeb is a ruthless activist investor known for his scathing public letters to company executives. His high-profile interventions include Yahoo, Sony, and Nestlé, where he pushed for drastic changes to boost shareholder value.

> Bill Ackman: Head of Pershing Square Capital, Ackman is a polarizing investor famous for both massive wins and high-profile losses. His aggressive short bet against Herbalife, calling it a pyramid scheme, turned into a prolonged and public battle with rival Carl Icahn. He also suffered a disastrous $4 billion loss on Valeant Pharmaceuticals.

> Nelson Peltz: Founder of Trian Partners, Peltz is a corporate raider turned activist investor known for targeting major brands like Procter & Gamble, Wendy’s, and Disney. His push for board seats and restructuring often leads to intense boardroom battles.

Each week we profile the most notorious investment stories.

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