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In 2016, Southern California real estate soared to new heights with the $100-million sale of the Playboy Mansion. The market-defining deal was the largest in L.A. County history at the time, and soon after, owners of iconic California estates brought them to market in hopes of securing similar fortunes.

One of those was attorney Leonard Ross, owner of the iconic Hearst estate in Beverly Hills. Weeks after the Playboy Mansion sold, he listed the trophy home for $195 million but couldn’t find a buyer.

Five years later, he faces a debt of more than $50 million on the estate. As a result, the famous residence with ties to William Randolph Hearst, John F. Kennedy and “The Godfather” will be auctioned off to the highest bidder Sept. 14, according to a court document obtained by The Times.