The Playboy Murders and Holly Madison Look Back on Decades-Old Cold Case Involving Ex-Playmate’s Boyfriend

A new season of Research Discovery The Playboy Murders premieres Monday, and the first episode tells the twisted story of a shocking double homicide involving a former Playboy girlfriend.

The premiere episode, titled “Double Trouble,” deals with the murder of the boyfriend of former Playboy cover model Sandy Bentley, whose relationship with Hugh Hefner changed the way future Playboy friends were treated at the Playboy Mansion.

Bentley and her twin sister Mandy dated Hefner and lived in the Playboy Mansion in 1999 and 2000, shortly after he split from wife Kimberley Conrad. But Sandy’s ensuing affair with a prominent financier brought her into conflict with the late publisher of Playboy. From there, her story becomes even more incredible.

In an exclusive clip shared with PEOPLE, executive producer and former friend Holly Madison says the fallout from Hefner’s relationship with the Bentley twins has made him wary of future girlfriends.

“When I moved into the mansion, things weren’t as luxurious and I think it was because he felt so burned by that first relationship after the wedding that he was a lot more careful with his girlfriends about how to move forward,” Madison says in the exclusive clip.

Sandy and Mandy Bentley.

Richard Corkery/NY Daily News Archive via Getty

So what happened to Sandy Bentley after her relationship with Hefner?

She became involved with Mark Yagall, a financier who bought Sandy numerous gifts and jewelry during their relationship. However, everything came to a halt when Yagalla was arrested for running a Ponzi scheme. (He pleaded guilty to securities fraud in 2003.)

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But Sandy’s next relationship will end in real tragedy.

In 2002, Michael Tardio and Christopher Monson were found shot to death in the back of an SUV in the Hollywood Hills.

Sandy began dating Tardia after Yagalla’s arrest and, along with his friend Monson, allegedly hatched a plan to sell jewelry Yagalla had purchased that the federal government had previously tried to seize, according to authorities interviewed for the episode.

But the plan went horribly wrong, and Tardio and Monson were shot and killed on the night of the proposed sale, presumably by the agreed buyer. The murders remained unsolved and the jewels were never found.

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Holly Madison

Holly Madison.

Warner Bros Discovery

Madison, who dated Hefner after the Bentley twins, remembers hearing about the murders while living in the mansion. “I remember at the dinner table one night, not long after I moved in, one of Hef’s friends told me a story about the murder of Sandy’s boyfriend at the time and one of his friends, and all the events leading up to it and everything that happened,” Madison tells PEOPLE in an interview. “And it was so weirder than the fictional kind of true story.”

Madison hopes so The Playboy Murders could lead to a break in the case, which is now more than 20 years old.

“Probably the best case scenario that could come out of this is that some answers can be found,” Madison says. “Maybe by putting the spotlight back on those stories, someone will come forward or someone will remember something or something will come to light.”

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The second season of The Playboy Murders premieres Monday at 10pm Eastern on ID.

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Source: HIS Education

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