Holly Madison Reveals What Led to Her Fallout With Kendra Wilkinson

If you watched The Girls Next Door and thought Holly Madison, Bridget Marquardt, and Kendra Wilkinson were just three women living their best lives with Hugh Hefner in the Playboy Mansion, Holly would like a word. She moved in at 22 thinking it would be a quick, wild chapter she’d close in a year or two, but it stretched into seven.

On Let’s Be Honest with Kristin Cavallari, she gets into all of it: what Hef was really like behind the cameras, why she and Kendra haven’t spoken in over a decade, and what it actually took to walk away. Here are the highlights, adapted from the episode.

Holly Madison Playboy Secrets: Hugh Hefner, Kendra Wilkinson

Knowing what you know now, would you still move in? 

“I don’t know if I would have gone there if I would have known any different. But if I was going to put myself on the same path and be like, ‘okay, you’re going to be there, you’re going to be on the show, and you’re going to be here now,’ if I could have changed my attitude a bit, I just would have been like, don’t believe boys and just look at this as transactional as it’s supposed to be. Because [Hefner] was very, like, he always described himself as a romantic, and whoever his main girlfriend was, he would do this kind of playing house thing that felt very real to me. So I ended up getting really attached.”

You’ve described the mansion as cult-like. Where was all of that coming from?

“Definitely coming mostly from Hef, also from the other girls, because before it was just me, Bridget, and Kendra, there were a rotating cast of like six other slots, and nobody got along. It was super competitive. 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. 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. I thought it was going to be this crazy thing I did for a couple of years while I was in college, and then I’d move on and everybody would forget about it. But 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.”

What were the rules like? 

“The most famous one was the nine o’clock curfew. And I knew that existed before I moved in, but at the time it didn’t really bother me because I thought, well, I’m just going to live here for like a year max…but obviously, as I’m there for seven years and haven’t been allowed to earn any trust in the relationship, I’m still not allowed to go visit my family for a week or anything like that. Then it started to get really ridiculous for me.”

How real was The Girls Next Door?

“Definitely manipulated storylines. 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. 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.”

But it ultimately saved your life?

“Compared to my entire story with Playboy, the show saved my life. That gave me an out. That gave me an excuse to do other things because he wouldn’t let us travel. He wouldn’t let us do jobs outside of Playboy. But once we needed storylines for the show, he started to let us do that because he loved the show so much. So the things I was allowed to do because of the show were really empowering and gave me the confidence to finally move on.”

How did Hef react when you tried to leave? 

“He wasn’t really taking it seriously that I wanted to leave. He kept trying to get me back. 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 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.”

You and Kendra haven’t spoken in over a decade. What happened?

“The same guy who did Girls Next Door was also producing my spinoff and Kendra’s spinoff. And just as the years went on, he was getting really crazy with us as far as trying to get us to do certain things and motivate us by making us jealous of each other. He would come to me and be like, ‘Okay, that’s cute, all that stuff you’re doing in Vegas, but you know Kendra’s on the cover of all these magazines that people see when they’re not in a Vegas hotel room.’ Or he would go back to Kendra and be like, ‘You know what, we need plotline for your show. You’re not doing anything, but Holly’s making all this money out here, so why doesn’t she come over and you ask her about it?’ And then I’d come over and Kendra would be weird…

…And then Kendra was really wrapped up in the tabloid cycle. So if she needed like a feud to be mentioned that week, she would say she was never friends with me and I called her out on that over text and that didn’t go well.”

What does happiness look like for you today?

“I feel like I’m out of fight or flight for the first time in my adult life. I think part of it is my new podcast I’m working on where I’m interviewing people. It’s called You Wish, and I love it. And just where I’m at with my family and friends…everything’s good.”

Listen to the full episode on Let’s Be Honest with Kristin Cavallari, available wherever you listen to podcasts.

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