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.