Carl Icahn: From Princeton Philosophy to TWA, Apple, and the $20 Billion Activist Empire

In 1985, a forty-nine year old former Princeton philosophy student and one-time medical school dropout named Carl Icahn launched a hostile takeover of Trans World Airlines. He had been operating for seven years as a corporate raider, taking large positions in undervalued companies and pressuring management to either restructure for shareholders or buy him out at a premium. The TWA campaign was different in scale. The airline was a major American institution. The takeover battle would play out across financial pages and union meetings for the better part of a year. By the time Icahn emerged as the controlling shareholder, he had become the most controversial corporate figure in America, and the term “corporate raider” had become permanently associated with his name.

What happened next is part of every business school case study on the leveraged buyout era. Icahn took TWA private in 1988 through a six hundred and fifty million dollar stock buyback that returned most of his original investment. He then sold off the airline’s most valuable asset, the London Heathrow routes, to American Airlines in 1991 for four hundred and forty-five million dollars. He emerged from the transaction with a four hundred and sixty-nine million dollar profit and walked away. The airline he left behind was carrying five hundred and forty million dollars in debt, would file for Chapter 11 bankruptcy in 1992, and would eventually be sold to American Airlines in 2001 after multiple subsequent bankruptcies.

The TWA episode crystallized everything that made Carl Icahn one of the most consequential investors in American financial history. The willingness to deploy capital aggressively against entrenched management. The analytical capacity to identify hidden value in conglomerate structures. The temperamental discipline to hold positions through extended takeover battles. And, more uncomfortably, the comfort with outcomes where the value Icahn extracted for shareholders came at substantial cost to other stakeholders, including employees, retirees, and the long-term viability of the underlying business.

Across the forty-three year period from 1968, when Icahn founded his first investment firm, through 2011, he compounded capital at approximately thirty-one percent annually. The S&P 500 over the same window compounded at approximately seven percent. The compounding gap is what produced the personal fortune that, at its peak, exceeded twenty billion dollars and that funded the Icahn School of Medicine at Mount Sinai, the Icahn Enterprises holding company, and the various activist campaigns he has continued to wage into his ninth decade.

This is the story of how a Queens-born philosophy student became the most influential corporate raider of his generation, what he built across four decades of hostile takeovers and activist campaigns, and what his career means for working traders trying to think structurally about the gap between market price and underlying value.

Far Rockaway, Princeton, and the medical school escape

Carl Celian Icahn was born on 16 February 1936 in the Far Rockaway neighborhood of Queens, New York City. He grew up in a working-class Jewish family. His father was a cantor and substitute teacher. His mother was a schoolteacher. The household was not poor, but it was modest, and Icahn has subsequently described feeling intensely from an early age that he wanted more than the trajectory his neighborhood would have given him.

He attended public schools in Queens and was an exceptional student. The combination of academic capacity and the determination to escape the limits of his upbringing produced what was, in 1953, an unlikely outcome for a Far Rockaway kid. Icahn was admitted to Princeton University. He was the first person from his Queens neighborhood to attend Princeton in living memory. The cultural distance between Far Rockaway and the Princeton of the 1950s was enormous, and Icahn has subsequently described the four years there as both intellectually transformative and personally isolating.

He majored in philosophy at Princeton. The choice is unusual for someone who would eventually become one of the most aggressive financial operators in American history, and the connection between the philosophy training and the trading career is more direct than it might first appear. Icahn’s senior thesis was on the empiricist criterion of meaning. The intellectual habits the philosophy training produced, the willingness to question fundamental assumptions, the capacity to think clearly about complex arguments, the discipline to follow arguments to their logical conclusions even when those conclusions are uncomfortable, would inform every subsequent year of his investment career.

After Princeton, Icahn enrolled at New York University School of Medicine. The decision was driven partly by his mother’s preference and partly by his own uncertainty about what he wanted to do with his life. He spent two years at NYU before dropping out. The decision was not casual. Medical school was, in 1959, one of the most prestigious career paths available to a Princeton graduate, and abandoning it required Icahn to disappoint his family and to acknowledge that he had no clear alternative direction.

He served briefly in the U.S. Army Reserve, then began looking for work on Wall Street. The transition was difficult. He had no finance background, no family connections in the industry, and no obvious credentials beyond his Princeton degree. He took a job as a stockbroker at Dreyfus and Company in 1961, beginning what would become a six decade career in financial markets.

Icahn & Co. and the options arbitrage years

Icahn worked at several brokerage firms during the early to mid-1960s, learning the mechanics of equity trading and developing his analytical framework. By 1968, he had accumulated enough capital and enough confidence to launch his own firm. Icahn and Company was founded that year as a securities firm focused on arbitrage and options trading. The early specialization is significant. Options markets in 1968 were relatively primitive compared to what would emerge in the 1970s, and the arbitrage opportunities for analysts willing to do detailed work were substantial.

The arbitrage and options work produced steady returns through the late 1960s and 1970s and gave Icahn the analytical foundation he would later apply to his activist campaigns. He learned to identify mispricings between related securities. He learned to evaluate corporate capital structures and the implicit options embedded in them. He learned to size positions based on the structural certainty of the underlying mispricing rather than on enthusiasm about the underlying companies. The skills transferred directly when he began taking activist positions in operating companies.

By 1978, Icahn had decided that the most attractive opportunities were no longer in arbitrage between related securities but in the much larger gap between the market value and the underlying business value of operating companies. The shift coincided with a structural change in American capital markets. The post-World War II era of conglomerate building had produced corporate structures where many of the underlying business units were worth substantially more than the market was assigning to the parent company. The opportunity for an analyst willing to take controlling positions and force restructurings was, in retrospect, enormous.

The Tappan campaign and the activist template

Icahn’s first major activist position was in Tappan Company, a manufacturer of stoves and ranges based in Mansfield, Ohio. He began accumulating shares in 1977 and 1978, eventually building a controlling position. The company was being managed conservatively by descendants of the founder, with substantial assets but limited capacity to deploy them productively. Icahn pushed for the sale of the company to a strategic buyer, eventually negotiating a transaction with Aktiebolaget Electrolux that produced a substantial premium for Tappan shareholders.

The Tappan campaign established the template Icahn would deploy across his subsequent career. Identify a company where the market value substantially understated the value of the underlying business assets. Build a controlling or near-controlling position quickly enough to avoid driving the price up too much before the position was complete. Use the controlling position to either pressure management into restructuring decisions that would unlock value, or force a sale to a strategic buyer who would pay full value for the operating assets. Exit at the higher valuation and redeploy the capital.

The structural insight underneath the template is that markets systematically undervalue companies where management is not making decisions to maximize shareholder returns. Conservative management, family-dominated boards, and dispersed shareholders create conditions where the gap between market value and intrinsic value can persist for years. Activist investors can close that gap by taking large positions and using shareholder rights to force decisions that management would not otherwise make. The intellectual humility to recognize that markets are not always efficient, combined with the operational capacity to deploy capital large enough to force management changes, is the structural framework that produced Icahn’s career.

The 1980s and the corporate raider era

The decade following the Tappan campaign was the most aggressive period of Icahn’s career. The 1980s combined three structural conditions that were unusually favorable for activist investing. First, the conglomerate-building era of the 1960s and 1970s had produced corporate structures with substantial hidden value. Second, the development of high-yield debt markets, particularly through Drexel Burnham Lambert and Michael Milken, gave activist investors access to financing for hostile takeovers at a scale that had not previously been possible. Third, the regulatory environment under the Reagan administration was relatively permissive of hostile takeovers, with antitrust enforcement and shareholder litigation rules generally favoring activist investors over entrenched management.

Icahn deployed capital aggressively across this environment. The campaigns of the 1980s included Marshall Field, ACF Industries, Dan River, Phillips Petroleum, Chesebrough-Pond’s, Texaco, USX, and Trans World Airlines. The pattern was consistent. Icahn would identify a company with hidden value or strategic weakness. He would build a position, often financed in part with high-yield debt. He would either negotiate a friendly sale at a premium or launch a hostile takeover. In several cases, he would accept “greenmail” payments, where the target company would buy back his shares at a premium to make him go away. The greenmail payments were legal at the time but became one of the more controversial features of 1980s corporate raiding.

The Texaco campaign of 1988 is a representative example. Icahn accumulated approximately thirteen percent of Texaco’s stock during the company’s bankruptcy proceedings related to its dispute with Pennzoil. He pushed aggressively for restructuring and for management changes. He did not gain control of the board, but the pressure he applied during the bankruptcy resolution period drove the share price substantially higher. By June 1989, he was able to sell his Texaco stake for approximately two billion dollars, producing a profit of approximately seven hundred million dollars on the position. The sale was at the time the largest single share transaction in the history of the New York Stock Exchange.

TWA: the campaign that defined the reputation

The TWA takeover began in 1985 and continued in various forms until the airline’s bankruptcy in 1992. The campaign is the single episode most associated with Icahn’s reputation as a corporate raider, and the most honest account engages with both what Icahn extracted from the situation and what was lost in the process.

Icahn began accumulating TWA shares in early 1985, eventually building a controlling position over the resistance of incumbent management. The hostile takeover battle was bitter, public, and politically charged. The airline’s unions opposed the takeover, fearing that Icahn would extract value through asset sales and cost cuts at the expense of employees. Management argued that Icahn had no operational experience in airlines and would damage the company’s long-term competitive position. Icahn argued that TWA was being managed for the benefit of incumbent management rather than for shareholders, and that more aggressive financial discipline would unlock substantial value.

The takeover succeeded in 1985. Icahn became chairman of TWA. He spent the following three years implementing aggressive cost-cutting measures, negotiating new union contracts, and rationalizing the route network. In 1988, he took TWA private through a six hundred and fifty million dollar stock buyback, allowing him to recover most of his initial investment while retaining ownership of the airline. The buyback was financed through high-yield debt that loaded the airline with substantial obligations. In 1991, he sold TWA’s London Heathrow routes to American Airlines for four hundred and forty-five million dollars, recovering an additional substantial portion of his investment.

By the time Icahn departed in 1993, TWA had been left with approximately five hundred and forty million dollars in debt, had lost its most valuable international routes, and was structurally weaker than it had been before the takeover. The airline filed for Chapter 11 bankruptcy in 1992 while still under Icahn’s control. It would file for bankruptcy two more times in the following decade before being sold to American Airlines in 2001, ending its existence as an independent airline.

Icahn’s net profit on the TWA campaign is estimated at approximately four hundred and sixty-nine million dollars. The profit was real and substantial. The cost to TWA’s employees, retirees, and long-term competitive position was also real and substantial. The structural lesson for working traders is that the same arithmetic that produces extraordinary returns for activist investors also produces externalities that the financial returns do not capture. The trader who ignores the externalities is making a moral choice, not just an analytical one.

The 1990s: RJR Nabisco and the transition

The 1990s were a period of consolidation for Icahn’s operating model. The high-yield debt market that had financed many of the 1980s campaigns had been damaged by the collapse of Drexel Burnham Lambert in 1990. Regulatory and legal protections for incumbent management had strengthened in response to the worst excesses of the 1980s. Greenmail payments had become socially unacceptable and legally restricted.

Icahn adapted. He continued to take activist positions but moved away from the most aggressive hostile takeover tactics of the 1980s. The campaigns of the 1990s included Marvel Comics, Western Company of North America, and most notably RJR Nabisco. In December 1998, Icahn led an investor group that acquired a five percent stake in RJR Nabisco and began pressuring the company’s management to separate its tobacco and food businesses. The separation thesis was straightforward. The tobacco business was being penalized by the conglomerate structure because of its regulatory exposure, and the food business was being undervalued because of its association with tobacco. Separating the two would, in Icahn’s analysis, produce more accurate valuations of both. He was largely correct.

The 1990s campaigns produced steady returns without the cultural drama of the 1980s takeovers. Icahn was repositioning his public image from “corporate raider” to “shareholder activist,” and the change in framing was significant. The underlying activity was substantially the same. The cultural framing was different. Activism was acceptable in a way that raiding had not been by the late 1990s.

Icahn Partners and the hedge fund era

In 2004, Icahn raised three billion dollars to launch Icahn Partners, a hedge fund that institutionalized his activist approach within a more traditional fund structure. The decision reflected a broader shift in the activist investing landscape. The strategy had moved mainstream. Multiple hedge funds were now operating with similar approaches. The structural opportunities that had been available to Icahn alone in the 1970s and 1980s were now competed for by a growing cohort of activist managers including Bill Ackman, Daniel Loeb, and others.

The Icahn Partners fund and the broader Icahn Enterprises platform allowed Icahn to scale his approach across a larger number of simultaneous campaigns. The 2000s and 2010s campaigns included Time Warner, Yahoo, Motorola, eBay, Dell, Apple, Netflix, Chesapeake Energy, Herbalife, and many others. The scale of capital deployed in each campaign was larger. The number of simultaneous positions was larger. The institutional infrastructure required to manage the operation was more extensive.

The Apple campaign of 2013 to 2016 is a representative example of the modern Icahn approach. He acquired a substantial position in Apple stock and publicly advocated for the company to dramatically increase its stock buyback program. Apple’s management, under Tim Cook, eventually authorized substantial increases in the buyback program. Icahn’s position appreciated significantly during the period he held it. He sold most of his position in 2016, producing approximately two billion dollars in profits on the trade. The campaign was conducted entirely through public advocacy and shareholder pressure rather than through a hostile takeover. The structural shift from 1980s raiding to 2010s activism was complete.

The framework: structural arbitrage between price and value

Icahn’s career rests on a small number of structural insights that, properly understood, translate into a framework working traders can adapt to their own scales of operation.

Markets systematically undervalue companies with weak governance. The single most reliable source of mispricing in equity markets is the gap between underlying business value and market value created by management decisions that do not maximize shareholder returns. Conservative management, dispersed shareholders, and entrenched boards create conditions where this gap can persist for years. The activist investor’s edge is the willingness to identify the gap, build a position large enough to force change, and then push for the changes that will close the gap.

The threat of action is often more valuable than the action itself. Many of Icahn’s most profitable campaigns produced returns through the share price appreciation that followed the announcement of his position, before any restructuring actually occurred. The market would price in the probability that Icahn’s involvement would force changes, and the share price would rise. In some cases, the campaigns produced no actual restructuring but still produced substantial returns because management would buy back shares from Icahn at a premium to avoid the prolonged battle. The structural insight is that the credibility of the threat matters as much as the execution. The trader who has reliably executed in the past has option value in every subsequent campaign that the inexperienced operator does not.

Reserves matter more than initial position size. Icahn has frequently said that in takeovers, the metaphor is war and the secret is reserves. The principle is that activist campaigns often take longer than anticipated and require additional capital deployment as the campaign develops. The investor who deploys all available capital in the initial position has no capacity to add when prices move against the position or when management’s defensive measures require more aggressive responses. The investor who maintains reserves can respond to changing conditions and can scale the position when the structural opportunity demands it. The retail equivalent of this principle is to maintain capital reserves for adding to high-conviction positions during drawdowns rather than deploying all available capital on the initial entry.

Process matters more than any single trade. Icahn’s thirty-one percent annualized returns over forty-three years were not produced by any individual brilliant campaign. They were produced by the consistent application of the activist framework across hundreds of campaigns over four decades. Some campaigns produced spectacular returns. Some produced losses. Some produced modest profits. The compounding came from the consistency of the process. The discipline to apply the same analytical framework across cycles, across market environments, and across the inevitable variation in individual outcomes is what produced the long-term record. The discipline to maintain process consistency through difficult periods is the structural feature that distinguishes long-term great investors from those who produced one or two great years and then disappeared.

The Icahn Enterprises era and the recent challenges

Throughout the 2000s and 2010s, Icahn increasingly conducted his investment activities through Icahn Enterprises, a publicly traded diversified conglomerate that he controls. The structure allowed retail investors to participate in his investment activities through publicly traded shares, while giving Icahn a permanent capital base that did not face the redemption risk that traditional hedge funds confront. The structure also produced complications that became more visible in subsequent years.

In May 2023, the short-selling firm Hindenburg Research published a critical report on Icahn Enterprises, arguing that the company was structurally overvalued, that its dividend payments were not sustainable, and that the company’s accounting practices created risks that public investors were not appropriately pricing. The Icahn Enterprises share price collapsed in response, falling more than fifty percent over the following months. Icahn himself faced margin calls related to personal loans collateralized by Icahn Enterprises shares. He was forced to renegotiate the loan structure to avoid forced liquidation of his stake.

The episode is part of the public record and is worth engaging with honestly. Icahn has been one of the most successful investors of the past half century. He has also, in his late eighties, encountered structural difficulties that the framework he built over decades did not anticipate. The difficulties do not invalidate the historical record. They do illustrate that even the most successful frameworks have edges where their effectiveness diminishes. Working traders should think carefully about what conditions made Icahn’s framework work for forty years and what conditions might be different in the current environment.

What Icahn means for your trading practice

Icahn’s career maps onto Mind, Method, Money in ways that translate directly to retail traders, partly because the structural insights that drove his career do not depend on the institutional scale of his operations.

Mind. Develop the temperamental capacity to act on analytical conviction when management and consensus disagree. The activist framework requires a specific psychological profile. The investor who needs validation from management or from the broader market while building a position cannot operate in the situations where the activist framework produces its highest returns. The retail equivalent is not to launch hostile takeovers, but to develop the psychological framework that allows you to deploy capital in situations where the consensus, or the company’s management, is telling you that you are wrong. The structural opportunities are concentrated in those situations precisely because most investors cannot tolerate operating there.

Method. Look for situations where governance failures have created persistent gaps between market price and underlying value. Most retail traders cannot deploy enough capital to force corporate restructurings, but the structural insight that drove Icahn’s career applies at smaller scale. Companies with weak governance, family-dominated boards, or entrenched management tend to trade at discounts to their intrinsic value. The discounts persist until something happens to close them, whether that something is an activist campaign, a strategic acquisition, or a generational transition in management. The retail trader who can identify these situations and hold positions through the time required for the discount to close has access to one of the most reliable sources of structural mispricing in equity markets.

Money. Maintain reserves. The single most consistent operational discipline in Icahn’s career has been the maintenance of capital reserves that allow for additional deployment when opportunities develop. Most retail traders deploy their full capital base on initial entries and have no capacity to add to positions during drawdowns or to scale positions when conviction increases. The discipline to maintain twenty to thirty percent of capital in reserves, even when the opportunity set looks attractive, is what distinguishes the operators who can compound through cycles from those who get forced out at the worst possible moments.

The last word

Carl Icahn is now in his late eighties. He continues to operate Icahn Enterprises and to wage activist campaigns across multiple American companies. His personal net worth, which peaked above twenty billion dollars in the 2010s, has declined substantially in the wake of the Icahn Enterprises share price collapse and the broader market environment of recent years. He remains one of the most consequential financial figures of the past half century, and his influence on the American corporate governance landscape has been more durable than the financial returns of any single campaign.

The thirty-one percent annualized returns over forty-three years stand as one of the most extraordinary track records in the history of active management. The returns were not produced by any individual brilliant trade. They were produced by the consistent application of the activist framework across hundreds of campaigns over four decades. Tappan in 1978. ACF Industries and Marshall Field in the early 1980s. Phillips Petroleum, Chesebrough-Pond’s, Texaco, USX, and TWA in the mid to late 1980s. RJR Nabisco in the 1990s. Time Warner, Yahoo, Apple, Netflix, and many others in the 2000s and 2010s. The list is long because the framework was applied consistently across decades.

What Icahn leaves the working trader is a framework that, in its essential elements, translates to retail scale. Identify situations where governance failures have created persistent gaps between market price and underlying value. Build positions large enough to matter to your overall return. Hold through the time required for the gap to close. Maintain reserves to scale positions when conviction increases. Refuse to be forced out by short-term volatility. The compounding curve that produced more than twenty billion dollars in personal wealth was built on these principles. The retail trader who learns to apply them at smaller scale has access to the same structural insights that built the career.

The most uncomfortable element of Icahn’s legacy is also the most important to engage with honestly. The framework that produced extraordinary financial returns for Icahn and his investors also produced significant externalities, including the long-term damage to companies like TWA whose underlying viability was compromised by the financial extraction. Working traders should be clear-eyed about both sides of this. The activist framework is structurally powerful. It is also structurally indifferent to the costs imposed on stakeholders other than shareholders. Whether to operate within the framework, and how to think about the externalities, is a question every investor has to answer for themselves. The framework’s effectiveness does not relieve the investor of the moral responsibility for the choice.

“In takeovers, the metaphor is war. The secret is reserves.” — Carl Icahn

Frequently Asked Questions

Who is Carl Icahn?

Carl Celian Icahn is an American businessman, investor, and corporate raider turned shareholder activist. Born on 16 February 1936 in Far Rockaway, Queens, he founded Icahn and Company in 1968 as a securities firm focused on arbitrage and options trading, and began taking activist positions in operating companies in 1978. He is the founder and controlling shareholder of Icahn Enterprises, a publicly traded diversified holding company. From 1968 through 2011, he compounded capital at approximately 31% annually. He is widely regarded as one of the pioneers of modern shareholder activism and as one of the most successful active investors in American financial history.

What is a corporate raider?

A corporate raider is an investor who acquires substantial stakes in publicly traded companies, often through hostile means, with the intent of forcing changes in corporate strategy, management, or capital structure to unlock shareholder value. The term emerged during the 1980s leveraged buyout era when figures including Carl Icahn, T. Boone Pickens, and Saul Steinberg pioneered the approach. Modern practitioners typically prefer the term “activist investor,” which describes substantially the same activity in language that emphasizes shareholder rights rather than the adversarial nature of the campaigns. Icahn was the most prominent figure in the transition from corporate raiding in the 1980s to mainstream shareholder activism in the 2000s.

What was the TWA takeover?

In 1985, Icahn launched a hostile takeover of Trans World Airlines, eventually gaining control of the airline. He took TWA private in 1988 through a $650 million stock buyback financed with high-yield debt. He sold TWA’s London Heathrow routes to American Airlines in 1991 for $445 million. By the time he departed in 1993, TWA had been left with approximately $540 million in debt and had lost its most valuable international routes. The airline filed for Chapter 11 bankruptcy in 1992 while still under Icahn’s control and was eventually sold to American Airlines in 2001. Icahn’s net profit on the campaign is estimated at approximately $469 million. The TWA episode is the single campaign most associated with his reputation as a corporate raider.

What were Icahn’s annual returns?

From 1968 through 2011, Icahn compounded capital at approximately 31% annually. The S&P 500 over the same period compounded at approximately 7%. The compounding gap is what produced the personal fortune that, at its peak, exceeded $20 billion. The returns were generated through a combination of arbitrage and options trading in the early years (1968 to 1978) and activist investing in operating companies from 1978 onward. Performance in the 2010s and 2020s has been more mixed, weighed down by challenges at Icahn Enterprises in particular. The 31% long-term compound annual return places Icahn among the most successful active investors in American financial history.

What is Icahn Enterprises?

Icahn Enterprises is a publicly traded diversified conglomerate holding company controlled by Carl Icahn. The company is based in Sunny Isles Beach, Florida, and operates across multiple business segments including investment, energy, automotive, food packaging, real estate, home fashion, and pharmaceutical. The structure allows retail investors to participate in Icahn’s investment activities through publicly traded shares while giving him a permanent capital base that does not face the redemption risk of traditional hedge funds. The company has faced challenges in recent years, including a critical short-seller report from Hindenburg Research in May 2023 that contributed to a substantial decline in the share price.

What is shareholder activism?

Shareholder activism is an investment strategy that involves acquiring substantial stakes in publicly traded companies and using shareholder rights to push for changes in corporate strategy, management, capital allocation, or governance structure. Modern shareholder activism evolved from the corporate raiding tactics of the 1980s into a more institutionalized approach that operates through proxy contests, public advocacy, and constructive engagement with management. Icahn was one of the pioneers of the approach, and his career bridges the corporate raiding era of the 1980s and the modern activist era of the 2000s. The strategy has become mainstream and is now practiced by multiple specialized hedge funds.

What was Icahn’s Apple investment?

Icahn acquired a substantial position in Apple stock beginning in 2013 and held it until 2016. Throughout the period, he publicly advocated for Apple to dramatically increase its stock buyback program, arguing that the company’s cash position was excessive relative to its operational needs and that returning more cash to shareholders would close the gap between the share price and the company’s intrinsic value. Apple’s management, under Tim Cook, eventually authorized substantial increases in the buyback program. The share price appreciated significantly during the period Icahn held the position. He sold most of his stake in 2016, producing approximately $2 billion in profits on the trade. The campaign is a representative example of the modern Icahn approach: public advocacy and shareholder pressure rather than hostile takeover.

What is the Icahn School of Medicine?

The Icahn School of Medicine at Mount Sinai is a graduate medical school in New York City. It was renamed in 2012 in recognition of Icahn’s $200 million donation to the institution, one of the largest single gifts to a medical school in American history. The school is part of the Mount Sinai Health System and is one of the leading research medical schools in the United States. Icahn’s connection to medicine is partly biographical: he attended NYU School of Medicine for two years before dropping out in the late 1950s to pursue a career on Wall Street. The medical school donation reflects both his philanthropic interests in medical research and a connection to a profession he briefly pursued before finding his way to finance.