He was left with little beyond the Playboy Mansion's roof over his head.

By Jen Wieczner
September 29, 2017

When Hugh Hefner died in the Playboy Mansion Wednesday, the legendary magazine founder had a surprisingly low net worth, with little to his name besides that roof over his head.

As fans mourned the loss of the 91-year-old cultural icon while others were critical of his exploits, speculation began almost immediately over who would inherit the magnate’s remaining fortune, with several publications estimating Hefner’s net worth at upwards of $45 million. A thorough review of financial records and agreements, however, reveals a less glamorous truth: Hugh Hefner was worth relatively little at his death, Fortune has found.

Indeed, while Hefner collected a $1 million salary and enjoyed the privilege of essentially free housing, he owned virtually no tangible assets nor real estate. Although it has been widely reported that he sold the Playboy Mansion for $100 million to his next-door neighbor last year, Hefner likely received none of that money—because by then, he no longer even owned the property.

The situation dates back to 2011, when private equity firm Rizvi Traverse Management, in partnership with Hefner, bought Hefner’s company Playboy Enterprises (which in turn owns Playboy) and took it private for about $217 million. But Hefner didn’t actually put up the money, nor did he sell his stock. Instead, he just gave all his shares to Rizvi in exchange for a minority stake in the new company and a couple of simple promises: Hefner would receive an annual salary of $1 million, and he would be allowed to live out the rest of his life in the Playboy Mansion for rent of just $100 a year.

The merger agreements read like a will, with clauses referring to “HMH’s death” and the “posthumous term.” But in effect, they rendered Hugh Hefner a mere employee of the media company he created, known for nude magazine spreads and celebrating sexuality. In addition to taking the rights to the Playboy brand and iconic bunny head logo, the buyer got the license to Hefner’s name, signature, and even his own likeness. While the Playboy trademarks still account for more than $1 billion in annual sales, according to the company’s statement announcing Hefner’s death, none of those royalties directly contributed to Hugh Hefner’s worth.

The very same day the merger closed—March 4, 2011—the deed of the Playboy Mansion was transferred over to the company’s new owners, property records show. So when Daren Metropoulos bought the 12-bedroom house in 2016, it was the private equity firm Rizvi—through a shell company called “Mansion Holdings”—on the other side of the $100 million deal, according to the public records.

Ultimately, Hugh Hefner was effectively reduced to a million-dollar pensioner, living almost rent-free in Beverly Hills, Calif. Hefner still owned an estimated 36.7% of the surviving company, now called Playboy Enterprises International, according to Delaware state court documents, “so that he can continue bearing the risks and rewards of equity ownership,” the merger agreement says. But the shares entitled Hefner to nothing unless the company was sold or went public. When a prospective $500 million buyout of Playboy last year fizzled, so too did Hefner’s hopes of realizing any of his equity stake’s paper worth.

The prevailing guesses for Hugh Hefner’s current net worth are based on his 2009 divorce papers, ending his second marriage to Kimberley Conrad. Obtained by TMZ, the documents reveal assets of $43 million, not including his Playboy stock.

But that nest egg can go fast, particularly when you’re an aging rebel married to a Playmate a third of your age. (Hugh Hefner wed current wife Crystal Harris, now 31, in 2012.) The divorce documents also show that eight years ago, Hefner was spending $46,000 per month on food, entertainment and health care, plus more than another $20,000 a month on alimony. Add to that the nearly $54,000 in monthly rent and household expenses he was paying at the time, and Hefner has since burned through some $7.4 million on routine costs alone. It’s enough to more than wipe out the roughly $5 million he took home in salary after taxes, by Fortune’s calculations, over the same period.

Living on a fixed income didn’t seem to deter Hugh Hefner’s free-spending tendencies, either. And with multiple marriages came an accumulation of obligations. There was Hefner’s undisclosed legal settlement with ex-wife Conrad in 2010, a suit in which she sought $5 million. A few months later, he shelled out almost $1 million more to help buy the Los Angeles park that houses the Hollywood sign.

Then there was the reported $1.3 million Hugh Hefner ponied up for engagement rings (yes, there were two) and a Bentley for his new wife, Harris. Not to mention the $5 million Hefner dropped to buy her a house in 2013, or the $40,000 yacht she gained last year. Property records show that those assets are owned by the HMH Crystal Trust—an entity that very likely also contains a millionaire’s allowance, making up for what Harris reportedly gave up in her prenuptial agreement with Hefner.

Donating an average of about $250,000 each year to his charity, the Hugh M. Hefner Foundation, also took another $2 million bite of his net worth annually since 2009. The organization now has approximately $1.5 million in assets, and Hefner has said that he intended to bequeath his estate to philanthropy in addition to his four children.

But exactly how much net worth is left to pass down? A generous back-of-the-envelope estimate is that Hugh Hefner is worth $26 million, not accounting for price fluctuations in Hefner’s stock market and bond investments. The figure is likely to be significantly lower—perhaps closer to $15 million or less—assuming he gave more of his fortune away to Harris and other family members. (If he picked the right stocks, however, the profits might have replenished some of that dent.)

Split between the kids and a few good causes, it’s still the kind of money that most Americans only dream of when they buy lottery tickets. But for Hugh Hefner, who started Playboy in 1953 with just $8,000, as he once told Fortune, and was rich by the 1960s, it’s a relative pittance. Consider that he purchased the Playboy Mansion for $1.1 million all the way back in 1971. At its peak in 1999, his Playboy stock alone was worth some $250 million.

The tension between Hugh Hefner’s desires and his purchasing power came to a head in recent years when Playboy, struggling with a faded empire and dwindling advertising revenue, needed rescuing. In 2009, as pressure mounted on Playboy Enterprises to sell itself or go private, Hefner initially explored acquiring it outright himself, asking his advisors to determine whether it was financially feasible, according to merger documents. In the end, he decided not to participate as a buyer at all, though it’s not clear if he couldn’t afford to, or if it just wasn’t worth it to him. After all, with a lifetime pass to the Playboy Mansion playground, the man needed little else. As Hugh Hefner once famously said: “In my wildest dreams, I could not have imagined a sweeter life.”

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