Kendra Wilkinson-Baskett and Holly Madison Are Both Right, at Least About Themselves if Not Each Other

We'd ask where it all went wrong, but it was never really quite right between Hugh Hefner's former girlfriends

By Natalie Finn May 14, 2016 10:00 AMTags
Kendra Wilkinson, Holly MadisonRD/ Erik Kabik/ Retna Digital

Once upon a time Kendra Wilkinson-Baskett and Holly Madison were roommates, chummily living the high life as two of Hugh Hefner's three main squeezes.

The surreal party ended when Holly, and then Kendra, moved out of the Playboy Mansion in 2008, but both seemingly remained close to Hef, with Kendra even marrying Hank Baskett at her historic former residence in 2009.

But apparently life wasn't much of a party for Holly, at least in retrospect, and her personal revelations  over the past year have driven quite the wedge between her and Kendra, who has admitted to being "embarrassed" by the choice to shack up with Hef in exchange for a lifestyle but has refused to foist any blame onto the man himself.

The Girls Next Door Girl-a-Day Gallery

And just when you thought their feud was behind us—let alone behind them—the dust started swirling yet again when Kendra tweeted a blue streak at Holly in response to her onetime co-star's People magazine cover story, which revisited and expanded upon the disturbing memories Holly shared in her now year-old memoir Down the Rabbit Hole.


"I'm protecting Hef, I'm protecting myself, I'm protecting the things that actually made us famous," Kendra said Friday on SiriusXM's Morning Men with Evan Cohen and Mike Babchik, explaining why her first instinct was to fly off the handle.

"I am being truthful," she also insisted on Wake Up With Taylor, the Kendra on Top star making the SiriusXM rounds today. "It's what I saw constantly all the time…[Holly] wants to make you, like, 'Oh, I didn't do that. I never did that! Look away, look away!' But I'm saying, 'Dude, you're no better than I am.'"

Kendra called Holly's portrayal of herself as a victim of Hefner's manipulation "disgusting."

"She should refund Hef," she added.

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But was it Holly's recollection in Down the Rabbit Hole of Hef "being the manipulator" who "pitted" Holly, Kendra and Bridget Marquardt against each other the real tipping point in their relationship?

From what it sounds like now, there wasn't that much of a relationship to maintain in the first place.

Holly Madison and Kendra Wilkinson-Baskett's Complicated History: A Timeline of Frenemies Feuding

"At the end of the day, it's a very awkward situation 'cause it's not like we're The Spice Girls," Kendra also said Thursday on Fox 5's Good Day New York. "We dated an 80-year-old man at the same time. It's very awkward. She probably wants to distance herself from that situation. God bless her, she should. It's embarrassing because I saw some things that she probably doesn't want me to talk about."

It's far more likely, however, that Holly had her experience, Kendra had hers—and neither is lying as far as either one honestly believes.

Erik Kabik/RETNA/

Unlike Kendra, Holly—who's also now married with two children—did not move out of the Playboy Mansion because she had already found love with another guy. Instead, she had openly talked on The Girls Next Door about being ready to get married and start a family, and at the time she said she wanted that with Hefner.

"We were just growing apart. I wanted different things in life," Holly told the Chicago Tribune in November 2008, about two months after she left him and the Playboy Mansion life behind. "Hef is very routine and wants things the same way, and I just got older and to the point where I needed to move on and have new experiences. Hef will always be my best friend and I will always care about him so much, but he's very routine and he likes his life the way he likes it. I just feel like I needed to grow and do something different with my life."

Elayne Lodge/Playboy Enterprises

At the time, Hefner said he didn't realize how much she had been affected by him telling her, about six months beforehand, that he didn't plan on marrying again or having more children. He also said he was blindsided by the abrupt end of their relationship.

"The fact that she was depressed after that, I didn't know at all," he told USA Today shortly after Holly moved out. "That was a revelation in the last days and weeks. Quite frankly, we thought when the time came, we would make a combined statement and we expected that combined statement would be somewhere in the weeks and months ahead."

E! Networks

But Holly returned to the Playboy Mansion to be one of Kendra's bridesmaids in 2009 and helped Bridget throw a baby shower before the birth of Kendra's first child, Hank IV; and then in 2011, after Hefner got engaged to Crystal Harris, she went back to talk to him about in, her visit captured on camera for her show Holly's World.

"I have a lot of different feelings on it," Holly told E! News then about her ex's engagement. "I don't just feel one way. I kind of didn't want to put a generic statement out there, like, 'Congratulations!' because I felt everyone would see through that…I wanted to see him and Crystal and tell everybody face-to-face how I felt."

Ethan Miller/WireImage

Holly would then join Kendra in jumping to Hefner's defense after he and Harris broke up and, again in December 2011, when Harris wanted custody of their dogs.

"Why did you voluntarily give the dog to Hef (who loves him too) after u left, only to ask for him back a few months later?" Holly tweeted. She added, "@KendraWilkinson @hughhefner I agree!!! I'm so glad you said something, Kendra!!...dogs shouldn't be yanked from happy homes on a whim. She needs to quit attention-seeking!"

Of course, Harris and Hefner ultimately reconciled and they got married on New Year's Eve in 2012. Neither Kendra nor Holly was in attendance.

And when it came time for Holly to tie the knot with Pasquale Rotella in 2013, they picked Disneyland to hold their nuptials—and Kendra was not a member of the wedding.

Stars at Disneyland & Disney World

Kendra, meanwhile, became wholly engrossed in her own marital drama, much of which played out on Kendra on Top and, last year, Marriage Boot Camp: Reality Stars. So she had plenty on her plate already when Holly's book came out last June, calling Kendra "the fakest person [she'd] ever met," and she was presumably thrown for a loop.

Hefner's public reaction to Holly's book was this statement: "Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy, and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight."

Elayne Lodge/Playboy Enterprises

"I wrote the book not because I had an ax to grind or because I wanted a reaction from him," Holly said on The Wendy Williams Show in response to Hef's take. "I just wanted to tell my story and hopefully inspire other women if they're in a bad relationship or a bad situation, to move on and not feel branded by a choice they made or a person they're known to be with."

When the book came out, Bridget told Radar Online, "I like Holly and I'm friends with her. I'm happy for her that she wrote the book." Speaking of Kendra, she added, "I haven't seen or talked to her in years. It is crazy. We haven't had a falling out or anything. We just haven't talked."

But Kendra (whose reunion with Bridget just aired on Kendra on Top last week) immediately had all sorts of things to say about Down the Rabbit Hole.

"Holly, you can tell, had this ulterior motive every minute being at the Mansion, and that motive was—it was clear as day—she wanted Hef's kids, she wanted a piece of Playboy, and she wanted to marry Hef for, obviously, his will," Kendra told People last summer.

In response to that, Holly told E! News, "I don't know what she has against me. I think she's just still very much a part of the Playboy fold and she didn't experience exactly what I experienced when I was there. At the end of the day, I wish her the best."

Presumably—in addition to wanting to protect Hef as both a friend and, as she has since pointed out many times in calling Holly out, as the man who gave her a career—Kendra took issue with being called fake. In fact, who knows if she would have ever reacted the way she did if Holly hadn't written that.

But the fact that Holly's version of events differs from Kendra's doesn't mean that either one of them isn't calling it exactly as she sees it.

And while Holly seems content to boil the current state of their feud down to a difference in perspective, Kendra—who released her own memoir, Sliding Into Home, in 2011—still doesn't sound ready to dismiss this as an instance of she-said, she-said.

"Every day [Holly] wanted to be there," she also told Good Day New York Thursday. "Even towards the end it was, like, 'I want you two out of here so I can marry Hef.' And then all of a sudden this came out?"

Elayne Lodge/Playboy Enterprises

Asked if she thought Holly's enthusiasm at the time was genuine or if she was just playing for the cameras, Kendra answered matter-of-factly, "Well, that's her fault. That's everybody's fault, if they're fake like that."

Being with Hef, Holly "chose that," Kendra continued. "She redid herself to become this person and now she's trying to bury it. You either live in denial or you live in truth. You face the truth of your decisions in life, or you run, and she's trying to run and that's not going to work. That's why you're here, that's why you're writing books, because of Hef."

Holly's third book, The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention, comes out May 17.

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