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(Bloomberg) -- Bit by bit, billionaire Ronald O. Perelman is parting with his treasures.His Gulfstream 650 is on the market. So is his 257-foot yacht. Movers hauled crates of art from his Upper East Side townhouse after he struck a deal with Sotheby’s to sell hundreds of millions of dollars of works.He’s unloaded his stake in Humvee-maker AM General, sold a flavorings company that he’d owned for decades and hired banks to find buyers for stock he holds in other companies.What in the world is going on with Ron Perelman? His exploits on and off Wall Street have been tabloid fare in New York since the go-go 1980s. But now, at an age when most fellow billionaires are kicking back, Perelman, 77, is facing a range of financial challenges, most of all at Revlon Inc., his cosmetics giant.Once touted as America’s richest man, his wealth has dropped from $19 billion to $4.2 billion in the past two years, according to the Bloomberg Billionaires Index.Bankers, socialites and art collectors have been buzzing about Perelman since his investment company, MacAndrews & Forbes, said in July it would rework its holdings in response to the coronavirus pandemic and the ravages it caused to American businesses, including his own.“We quickly took significant steps to react to the unprecedented economic environment that we were facing,” Perelman said in a statement. “I have been very public about my intention to reduce leverage, streamline operations, sell some assets and convert those assets to cash in order to seek new investment opportunities and that is exactly what we are doing.”Read Ronald O. Perelman's full statement herePerelman also gave more prosaic reasons for the shift, including spending time with his family during lockdown and a desire for a simpler life.“I realized that for far too long, I have been holding onto too many things that I don’t use or even want,” he said. “I concluded that it’s time for me to clean house, simplify and give others the chance to enjoy some of the beautiful things that I’ve acquired just as I have for decades.”Graydon Carter, the former editor of Vanity Fair who’s known Perelman for three decades, said the shift in Perelman’s attitude is sincere.“Often when people say this sort of thing, it’s masking something else. In Ronald’s case, it’s true,” said Carter, who partnered with Perelman to reopen the Monkey Bar in Midtown Manhattan. “He has learned to love and appreciate the bourgeois comforts of family and home.”Carter described Perelman as a “charismatic swashbuckler” who once enjoyed evenings on the New York social circle a little too much. But he said Perelman is now “crazy about spending time at home” with his fifth wife Anna, a psychiatrist, and their two young sons.Richard Hack, who wrote a 1996 unauthorized biography of Perelman, is skeptical.“If you want a simpler life, you go buy a farm in Oklahoma, not sell a painting out of your townhouse in Manhattan,” Hack said. “If he’s selling his art, it’s because he needs cash.”The art includes Jasper Johns’s “0 Through 9,” priced in the $70 million-range, Gerhard Richter’s “Zwei Kerzen (Two Candles),” which went for more than $50 million and Cy Twombly’s “Leaving Paphos Ringed with Waves (I),” which found a buyer for about $20 million, according to people with knowledge of the matter, who asked not to be identified as the sales were private.“What he’s selling is as blue chip as it gets,” said Wendy Goldsmith, an art adviser in London.Some proceeds are slated to pay down loans from Citigroup Inc., according to people with knowledge of the arrangements. He also has loans from JPMorgan Chase & Co., Bank of America Corp. and UBS Group AG related to his artwork, filings show.These are not forced sales, said a spokeswoman for Perelman. She also denied a New York Post story that “The Creeks,” his 57-acre East Hampton estate, is being discretely marketed and said that he remains committed to his considerable philanthropy. Perelman is building a performing arts center in the Financial District, is vice chairman of the Apollo Theater, and sits on the boards of Columbia Business School and New York-Presbyterian Hospital.Read More: Billionaire Perelman Seeks to Reset Empire to Face New WorldIt’s a striking turn for Perelman, long celebrated and feared for engineering some of the most ambitious deals of the 1980’s and 1990’s, and for the litigation, divorces and corporate brawls he left in his wake.“He was imaginative, aggressive and innovative in ways that changed the financial landscape,” said investment banker Ken Moelis, a long-time Perelman adviser.But now, one of the original pioneers of the Michael Milken-fueled junk-bond takeover era is realizing that there’s such a thing as too much debt — especially during a pandemic.Take Revlon, which sits at the center of his empire.Its $365 million market value is a whisper of the $1.74 billion he paid for the company in 1985. He owns about 87% of Revlon and has full control over the firm, run by his daughter, Debra Perelman.For decades, it strained under a heavy debt load, forcing Perelman to provide loans or inject funds as he switched executives to pursue various turnarounds. The billionaire made clear in a Wall Street Journal interview that he “loved the business” and, for better or worse, it most defined him.Revlon, which was slow to respond to shifting trends 20 years ago, has more recently lost sales to smaller beauty companies that lured customers with social media. Now revenue is plunging further because of store closures. The company has $3 billion of debt, some of its bonds trade at 14 cents on the dollar and the company faces a cash crunch in November. A Revlon spokesperson declined to comment.His problems aren’t confined to lipstick. Perelman used his Revlon shares as collateral for MacAndrews & Forbes debt, filings show. The shares have plunged 68% this year, a decline that would typically require lenders to seek additional collateral or repayment of the loans.Shares of other companies in his portfolio, including Scientific Games Corp. and Vericast Corp., were also pledged against MacAndrews & Forbes debt. At least nine banks have claims against Perelman’s assets, including his art collection, house in the Hamptons and various aircraft. About $267 million in mortgages are linked to the firm’s Upper East Side headquarters in Manhattan and other buildings he owns.Perelman has made progress on plans to sell some of his holdings.MacAndrews & Forbes struck a deal this week to sell its 35% stake in Scientific Games to an Australian investment firm. KPS Capital Partners in July agreed to buy Perelman’s stake in AM General, the Indiana-based maker of Humvees and other vehicles, for an undisclosed amount. A $439 million deal to sell Flavors Holdings, a maker of sweeteners and food products, to Whole Earth Brands Inc. was completed in June.Further simplifying Perelman’s holdings, however, might be easier said than done.Revlon’s $3 billion of debt would be a concern for any potential buyer. And Vericast, a collection of marketing and payments businesses, has struggled to navigate industry changes while dealing with its own substantial debt burden. Two of its major revenue streams are check printing and print-based advertising, both in decline due to digital payments and online marketing. Its RXSaver and RetailMeNot units are being shopped, indicating it may be easier to sell the company in parts than as a whole.Read More: Perelman’s Coupon Company RetailMeNot Said to Weigh Sale OptionsEven art sales can be troublesome. A Francis Bacon painting belonging to Perelman, valued at about $15 million to $23 million, was pulled from auction at the last minute due to a lack of interest. The art collection — which contains some of the most valuable 20th century works, including sculptures by Alberto Giacometti and paintings by Mark Rothko and Ed Ruscha — is now responsible for more than a third of his fortune.There are signs that the turmoil is taking a toll within MacAndrews & Forbes, where several of Perelman’s most senior staff have exited in quick succession.In July general counsel Steve Cohen departed, followed by spokesman Josh Vlasto and James Chin, who headed the capital markets group. Chief Financial Officer Paul Savas resigned in June over irregularities with $5 million in insurance payments between Revlon and MacAndrews & Forbes. He was replaced by Jeffrey Brodsky, who according to his LinkedIn profile, has “an extensive background in crisis and turnaround management.”Still, those who know him well say any recent stumbles won’t define him.“Ronald has been dealmaking at the highest level for forty years,” Moelis said. “Even Michael Jordan missed a shot.”For more articles like this, please visit us at bloomberg.comSubscribe now to stay ahead with the most trusted business news source.©2020 Bloomberg L.P.