Ivan Boesky, the 1980s financier who was caught for insider trading and spawned the stereotype of the out-of-control stock trader on Wall Street, has died at the age of 87.
His death was confirmed by his daughter Marianne Boesky, who gave no further details about how he died, according to the New York Times reported.
Boesky’s blatantly illegal actions – which often involved handing over suitcases of cash in exchange for valuable stock tips – were partly the inspiration for the creation of the breakout character Gordon Gekko in Oliver Stone’s hit film “Wall Street.”
In 1986, Boesky’s decades-long existence in the financial industry, fueled by hostile corporate takeovers and arbitrage trading, landed him on the cover of Time Magazine.
Also in 1986, everything came to an abrupt end when federal authorities persuaded the hundred millionaire to sign a settlement admitting his insider trading.
He was sentenced to three years in prison and a $100 million fine, a record punishment at the time that marked the end of the wild, wild west on Wall Street.
Ivan Boesky, seen here in a helicopter flying over Lower Manhattan, served as one of the key influences for fictional Wall Street dynamo Gordon Gecko, known for the motto “Greed is Good”
Members of the media surround financier Ivan Boesky and his attorney as they arrive at federal court in New York City, where he pleaded guilty to a criminal charge stemming from his insider trading.
At his peak in the mid-1980s, Boesky had a net worth of $280 million (about $818 million today) and a trading portfolio of $3 billion (about $8.7 billion today).
Before he was caught in 1986, Boesky had an enviable rise that allowed him to own homes in Manhattan, Paris, Hawaii and, of course, his sprawling estate in Westchester County, where his ex-wife Seema Boesky still lives.
He and Seema moved to New York City in 1966, where the couple lived in an apartment on Park Avenue Seema’s father paid.
Getting money from his wife’s family became a pattern.
In the late 1960s, Boesky worked for investment firms LF Rothschild (which later went bankrupt during the stock market crash of 1987) and the company First Manhattan.
He then served as a general partner at the financial services firm Edwards & Hanley from 1972 to 1975, where he first demonstrated his risk appetite by betting millions on a single stock position and incurring a $10,000 fine for short-selling securities that were not t in his possession.
And when Edwards & Hanley went bankrupt, Boesky took $700,000 from his wife’s family to start his own arbitration firm, Ivan F. Boesky & Company.
Michael Douglas plays Gordon Gekko in the film Wall Street, inspired by Boesky
Boesky is featured on the cover of the December 1 issue of TIME Magazine.
Ivan Boesky pleads guilty on April 23, 1987 in the U.S. Courthouse for the District of New York
This is when his bets got a lot bigger.
He placed bets of up to $100 million on companies he thought were prime takeover candidates, even before any deals were announced.
To obtain the capital needed for these absurdly large bets, he lived on loans. And when he hit it big, Boesky kept 60 percent of the profits, while his partners would get the rest.
He also expected his partners to absorb as much as 90 percent of any losses they suffered.
The biggest deals he was involved in made him millions of dollars. He made $65 million when Chevron acquired Gulf, $50 million when Texaco bought Getty, and $50 million from Philip Morris’ acquisition of General Foods.
His takeover deals involving Nabisco Brands, Union Carbide and Boise Cascade were insider trading, the Securities and Exchange Commission said.
In the elite circles in which Boesky moved, people called him “Piggy” – sometimes referring to the size of his deals – or “Ivan the Terrible.”
An aerial view of Seema Boesky’s home in Westchester County, New York. The house is located in Bedford, an affluent city about 40 miles north of New York City. Boesky bought the house in the late 1970s for $850,000, but lost it during his divorce with Seema
Seema Boesky poses with her dog, Sashi, a Maltese, at her home in Westchester on May 4, 2006
Ivan Boesky’s 1985 book, “Merger Mania,” promoted his deal-making skills and talent for identifying takeover targets
He was known for going into expensive restaurants and ordering every dish on the menu, tasting them all and then choosing one dish to nibble on while ignoring the rest.
His flair for the extravagant didn’t stop there once he showed up to play tennis in a pink Rolls-Royce, the New York Times reported.
Boesky’s success was not his own. Of course, he started with a generous seed fund from his wife’s family, but he also had a close friendship and business relationship with the charismatic junk bond salesman Michael Milken.
The two were the titans of the financial sector in the early 1980s. They spoke daily and had their fingers deep in almost every high-profile corporate takeover, with Milken Boesky providing much of the capital for his wild transactions.
But when Boesky surrendered to the government in 1986, part of the deal was that he had to deal with Milken, who would be an even bigger catch for federal investigators.
He carried a wire to a meeting with Milken, and their subsequent recorded conversation led to Milken’s arrest in 1989 for racketeering and securities fraud.
Rudy Giuliani, then a federal prosecutor, holds a press conference about the Ivan Boesky case in New York City on April 23, 1987.
Despite being convicted of crimes even more serious than Boesky, Milken led a life marked by charitable acts. He founded the Milken Family Foundation before his death and this has been a major focus after he served his time
Ivan Boesky would live in this house in San Diego’s La Jolla neighborhood for many years. Former Republican presidential candidate and current Utah Senator Mitt Romney purchased the home in 2008
Milken paid a fine even higher than Boesky’s ($600 million) and spent 22 months in prison. President Donald Trump pardoned him in February 2020 and despite his crimes, Milken still has a net worth of $6.5 billion.
Compared to Milken, who still occasionally makes headlines with his charitable contributions, Boesky had a much quieter life after his conviction.
He spent 18 months in Lompoc federal prison, then a minimum-security prison known for housing white-collar criminals and mob bosses.
While there, he studied the Talmud and earned pocket money by working on a cleaning crew. He later admitted that the extra change went to paying fellow inmates to do laundry for him, which was against prison rules.
Fresh out of prison in 1990, his wife divorced him a year later. He claimed to have nothing to his name and begged Seema for half of her $100 million fortune, which he said came from his radically successful career on Wall Street.
Ultimately, Boesky received a $20 million lump sum from his ex-wife, annual payments of $180,000 and a $2.5 million home in San Diego’s La Jolla neighborhood.
He is survived by three children from his first marriage, Marianne, William, Theodore and Johnathan, as well as his second wife, Ana (Serrano) Boesky; their daughter, Blu; and four grandchildren.
Creepily, Boesky told the Washington Post in 1985, a year before he would plead guilty to a litany of crimes and bring Wall Street to its knees, that his downfall would be swift.
“I cannot predict my demise,” he said. “But I suspect it will happen abruptly.”