Ivan F. Boesky, a brash financier who came to symbolize Wall Street greed as a central figure of the 1980s insider trading scandals, and who went to prison for his misdeeds, died today at his home in the La Jolla neighborhood of San Diego. He was 87.

His daughter Marianne Boesky said he died in his sleep.

An inspiration for the character Gordon Gekko in Oliver Stone’s movie “Wall Street” and its sequel, Ivan Boesky made a fortune betting on stock tips, often passed to him illegally in exchange for suitcases of cash. His guilty plea to insider trading in November 1986 and his $100 million penalty, a record at the time, sent shock waves through Wall Street and set off a cascade of events that marked the end of a decade of frenzied takeover activity and the celebration of conspicuous wealth.

As federal investigators closed in on Boesky, he agreed to cooperate, providing information that led to the downfall of investment bank Drexel Burnham Lambert and its junk bond king, Michael Milken.

Boesky brought an aggressive style to the once-sleepy world of arbitrage, the buying and selling of stocks in companies that appear to be takeover targets. Sniffing out impending deals, he amassed stock positions at levels never seen before.

At the top of his game in the mid-1980s, he had a net worth of $280 million (about $818 million in today’s currency) and a trading portfolio valued at $3 billion (about $8.7 billion today), much of it financed with borrowed money. Home was a sprawling estate in Westchester County, New York, its main house adorned with a Pierre-Auguste Renoir painting and carpets embossed with his monogram, “IFB.” (The estate was once owned by the Revson family, founders of Revlon cosmetics and, before that, the family behind Macy’s, the Strausses.)

Besides a Manhattan pied-a-terre, there was a retreat on the French Riviera, a lavish Paris apartment and a condo in Hawaii. Through his first wife, Seema Boesky, he was part owner of the celebrated Beverly Hills Hotel, a lush pink concoction favored by Hollywood stars as well as by titans of finance attending the Predators’ Ball, Drexel Burnham’s annual get-together.

Ivan Boesky claimed to sleep only two to three hours a night, rising at 4:30 a.m. to work out before taking a limousine to his New York office, where he stood command over an array of video terminals, news wires and stock tickers, as well as 160 telephone lines and a set of screens allowing him to see and hear his employees at all times. Each day he dressed the same way: in a signature three-piece black suit and starched white shirt, with a gold chain dangling from his vest pocket. He preferred to stand all day than to sit, and he barely ate, consuming vast amounts of coffee instead.

‘Greed Is Healthy’

On Wall Street, it was a decade born of greed. Fueled by the easy money of junk bonds, a small group of kingmakers — including Carl Icahn, T. Boone Pickens, James Goldsmith, Saul Steinberg, Boesky and Milken — became fabulously wealthy by engaging in schemes of financial engineering and corporate raids that drove the stock market to dizzying levels before its crash in 1987.

Boesky embraced the go-go ethos of the time. “Greed is all right, by the way,” he told business school students at the University of California, Berkeley, in a commencement speech in 1986. “I think greed is healthy. You can be greedy and still feel good about yourself.” He was greeted with rousing applause.

A year later, those words were immortalized on screen in “Wall Street,” in which unscrupulous corporate raider Gordon Gekko (played by Michael Douglas) gives his famous “Greed is good” speech.

“All that mattered to Ivan Boesky was making money,” Jeff Madrick, author of “Age of Greed” (2011), said in an interview for this obituary in 2019. “He found a path to that and he abused it badly.”

Boesky touted his success whenever he could. In 1985, he published a book, “Merger Mania,” which promoted his deal-making skills and his uncanny ability to identify the next takeover target. But behind Boesky’s success was a story of deceit: He was paying others to provide him with insider information.

One of his biggest sources was Martin Siegel, at the time an investment banker at Kidder, Peabody & Co. The two hatched their scheme in 1982, and soon Boesky was having a courier deliver suitcases filled with $100 bills to Siegel — $150,000 one time, $200,000 another time and $400,000 a third — in exchange for inside information about forthcoming takeovers. Using the code words “red light” and “green light” for the handoff, the courier delivered the suitcases to Siegel in the lobby of the Plaza Hotel in Manhattan.

By 1986, Boesky’s world had begun to unravel. In May, when a lower-level Drexel banker, Dennis Levine, was indicted on insider-trading charges, federal prosecutors found Boesky’s name in his notes; he had been paying Levine for tips. Hot on Boesky’s trail was Rudy Giuliani, the U.S. attorney who had been bringing down Mafia dons and crooked politicians and was now focused on Wall Street malfeasance.

In September 1986, Boesky was invited to one of the most lavish bar mitzvahs in memory. Gerald Guterman, a real estate developer, paid nearly $1 million to rent the entire Queen Elizabeth II to celebrate his son, taking guests on a cruise up the Hudson River and out into the Atlantic. Huge banners, clowns, musicians and a crew of 1,000 greeted the guests. But Boesky was nowhere to be seen.

Claiming he had missed the sailing, Boesky staged his arrival: A helicopter descended from the sky and landed on the ship. As its blades whirred, guests craned their necks to watch as Boesky emerged in a tuxedo and black tie, by all accounts looking like a latter-day James Bond and completely upstaging the host family.

The next day, Sept. 17, Boesky surrendered to federal authorities and agreed to wear a wire in his conversations with Milken and others on Wall Street.

A Boy From Detroit

Ivan Frederick Boesky was born in Detroit on March 6, 1937, to Helen and William Boesky. His father was a Jewish immigrant from Russia. The family ran a string of restaurants under the name Brass Rail that became strip clubs as the city declined. The business eventually went bankrupt.

As a 13-year-old, and without a driver’s license, Ivan drove an ice cream truck for nickels and dimes. (In later years, he named one of his investment vehicles, Farnsworth & Hastings, after the street corner location of his family’s business.)

For a year, Ivan attended Cranbrook, a prestigious prep school outside Detroit, where he excelled at wrestling and in later years left many with the impression that he was an alumnus; he had actually left Cranbrook and graduated from Mumford High School, in middle-class Detroit.

He attended three colleges — Wayne State, the University of Michigan and Eastern Michigan — and graduated from none of them. It took him five years, after dropping out twice, to get a degree in 1964 from the Detroit College of Law. He got a one-year clerkship with a federal judge through connections, was rejected by Detroit’s top law firms and worked as an accountant at the local Touche Ross office.

Boesky’s marriage in 1962 to Seema Silberstein, a daughter of Ben Silberstein, a real estate developer who owned the Beverly Hills Hotel, catapulted him into a world of wealth and sophistication.

He was unable to find his professional footing until he was 27, when a former Cranbrook classmate who was working at Bear Stearns told him about arbitrage. Hooked on the idea, he moved to New York, where his father-in-law bought the young couple a Park Avenue apartment.

He cycled through jobs, working as a trainee at the investment banking firm L.F. Rothschild, an analyst at First Manhattan Co. and an arbitrageur at Kalb, Voorhis, where his losing $20,000 got him fired. In 1971, Boesky went to the brokerage firm Edwards & Hanly, where he first displayed his aggressive style, betting millions into a single stock position and incurring a $10,000 fine for selling securities — which he didn’t have — short.

By 1975, the firm was bankrupt, and Boesky decided to strike out on his own. Backed by $700,000 from his wife’s family, he started Ivan F. Boesky & Co.

The arbitrage business was accustomed to small, cautious investments in publicly announced takeovers, with hopes that the stock price would rise. But Boesky bet big.

He put down multimillion-dollar wagers — $10 million, and even $100 million or more — on companies that he thought might be takeover targets, before any deals were announced. He relied heavily on borrowed money and kept the bulk of any gains for himself: His partners would get 40%, and he would take 60%. His partners would absorb 90% of any losses, and he would take 10%.

On Wall Street, he was given two monikers: Piggy and Ivan the Terrible. He was known for going into fancy restaurants and ordering every dish on the menu, tasting them and then nibbling on one dish while ignoring the rest.

He once showed up to play tennis in a pink Rolls-Royce. And he loved to entertain at the Harvard Club in Manhattan, even though he had never attended Harvard University. (He made a large donation to the University’s School of Public Health, which named him to its board of overseers, making him eligible for club membership.) He told investors that he was an adjunct professor at Columbia Business School. The school said that was not true.

Boesky made an estimated $65 million when Chevron acquired Gulf, $50 million when Texaco bought Getty and $50 million from Philip Morris’ acquisition of General Foods. Other multimillion-dollar home runs — some helped by information that the Securities and Exchange Commission said was obtained illegally — involved deals with Nabisco Brands, Union Carbide and Boise Cascade.

Boesky’s closest ally in the world of finance was Milken, head of Drexel Burnham’s fabled junk bond desk in Los Angeles. The two spoke daily, with Milken arranging for much of the capital behind Boesky’s trades and Boesky becoming a profit center for Milken. Their fingers were on nearly every takeover deal, their every move followed in the financial press.

After turning himself in to federal investigators, Boesky, in an appeal for leniency, agreed to become a government informant, wearing a wire when meeting with Milken, who was an even bigger target of federal prosecutors.

“Milken and Boesky were deeply intertwined in what was a sweeping criminal conspiracy,” James B. Stewart wrote in his book “Den of Thieves” (1991). “Taken together, the ventures were practically a catalog of securities crimes, starting with insider trading, and including false public disclosures, tax fraud and market manipulation, as well as a slew of more technical crimes.”

In the end, Milken, too, would end up in prison and pay an even bigger fine: $600 million. In February 2020, he received a pardon from President Donald Trump.

A Quieter Life

Boesky pleaded guilty to insider trading charges in November 1986 and agreed to pay $100 million — a $50 million fine and $50 million in repayment of illegal trading profits. (He was later able to deduct half of his $100 million penalty from his income taxes.)

In December 1987, Boesky was sentenced to a three-year prison term. He spent 18 months at the Lompoc federal prison camp, a minimum-security facility in Santa Barbara County, California, followed by four months at a Brooklyn halfway house. While in prison, he studied the Talmud and earned pocket change by working on a prison cleanup crew. He later admitted to violating prison rules by paying fellow inmates to do his laundry.

He emerged from prison in 1990. He was 53. In 1991, his wife of 30 years sued him for divorce. Pleading poverty, he asked for half of her $100 million fortune; he settled for $20 million, annual payments of $180,000 and a $2.5 million California home.

For many years, Boesky lived quietly in La Jolla, where he remarried and became a father again.

In addition to his daughter Marianne, he is survived by three sons from his first marriage, William, Theodore and Johnathan; his wife, Ana (Serrano) Boesky; their daughter, Blu Boesky; and four grandchildren.

In a 1985 interview with The Washington Post, Boesky gave a remarkably prescient view of his ultimate downfall. “I can’t predict my demise,” he said. “But I suspect it will occur abruptly.” It did. Within a year, he was arrested and charged with insider trading.

This article originally appeared in The New York Times.

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