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Holly Madison Reveals 'Grandpa' Hugh Hefner Would Coax Her Into Staying at Playboy Mansion by Leaving His 'Will Out on the Bed'

Photo of Holly Madison and Hugh Hefner
Source: MEGA

Holly Madison recalled Hugh Hefner's toxic attempts to get her to stay at Playboy Mansion.

May 7 2026, Published 5:00 p.m. ET

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Hugh Hefner reportedly employed a toxic means of convincing Holly Madison to stay at Playboy Mansion.

On the Tuesday, May 5, episode of the “Let’s Be Honest With Kristin Cavallari" podcast, the former Playboy Bunny, 46, revealed that the late magazine founder would ignore her desire to depart the “cult-like” mansion.

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Source: Let’s Be Honest With Kristin Cavallari/YouTube

Holly Madison appeared on the 'Let’s Be Honest With Kristin Cavallari' podcast.

“He wasn’t really taking it seriously that I wanted to leave. He kept trying to get me back,” Madison disclosed. “He would leave his will out on the bed on my side so I could see how much money was going to be left for me if I stayed…or after Kendra [Wilkinson] and I announced we were leaving, it was a big trend for tabloidy outlets to write like, ‘Oh, these girls just aren’t going to be famous anymore.’ So Hef would get all this stuff printed out and leave it out so I would see, hoping I would change my mind, like, oh my god, I can’t be irrelevant. I must stay.”

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Holly Madison Accuses Hugh Hefner of Pitting Girls Against Each Other

Image of Holly Madison never expected to stay so long at Playboy Mansion.
Source: Let’s Be Honest With Kristin Cavallari/YouTube

Holly Madison never expected to stay so long at Playboy Mansion.

Madison also accused Hefner of fostering a “super competitive” environment among the girls in the mansion.

“He liked to kind of play two different teams against each other, so he always felt fought over, and he could always get his way, and we couldn’t unionize against him,” she explained. “And I didn’t realize that was going on. I thought he was so great, and I thought it was just the girls being awful…but also coming from myself and just the fear and pressures I had. Because I was just this random girl from Oregon who felt like, okay, I made this decision.”

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Holly Madison Was 'Afraid to Leave' the Playboy Mansion

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Image of Holly Madison was manipulated by Hugh Hefner into staying at Playboy Mansion.
Source: Let’s Be Honest With Kristin Cavallari/YouTube

Holly Madison was manipulated by Hugh Hefner into staying at Playboy Mansion.

The 46-year-old assumed that Playboy was just a “crazy thing” she would do for a few years in college, then move on, but it wound up becoming a major part of her life, as she resided there for seven years.

“It became such a defining moment for me that I was afraid to leave because I just felt like I was going to be judged so heavily for my choices,” she emphasized.

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Holly Madison Hints 'The Girl Next Door' Wasn't Entirely Truthful

Image of Holly Madison starred on a reality show about the Playboy Mansion.
Source: Let’s Be Honest With Kristin Cavallari/YouTube

Holly Madison starred on a reality show about the Playboy Mansion.

Madison starred in The Girl Next Door, a reality TV series following the lives of Hefner’s girlfriends, including her. She alleged that the show — which ran between 2005 and 2010 — “definitely manipulated storylines.”

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Image of Holly Madison was Hugh Hefner's No.1 girlfriend.
Source: MEGA

Holly Madison was Hugh Hefner's No.1 girlfriend.

“It was definitely trying to clean the whole thing up and present it as like, oh, here’s this cute little grandpa and these three girls and maybe they’re doing stuff, maybe not,” she detailed. “You can decide for yourself, but it’s all very happy and sparkly and perfect. So that was definitely not real…they were always cutting to me rolling my eyes when I wasn’t and making it look like I was super jealous of all these people I wasn’t.”

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