Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny

by Holly Madison

  I assumed she had to work for Playboy or Jack Daniel’s or something. I mean, you had to be getting paid to be that bubbly, right?

  That evening, after freshening up, I wandered downstairs for dinner and heard someone blurt out, “You cut your hair!” My new look had been so poorly received that I wasn’t expecting any sort of compliments when I arrived in the great hall. Immediately, I spotted Miss Chiquita Banana sitting on the bench in a Clueless-inspired plaid skirt and matching top.

  “Oh yeah,” I finally replied, self-consciously running my hand under my new blond bob. “I donated it to charity.”

  “Oh, Locks of Love?” she asked, seeming genuinely interested.

  “Yeah,” I said, feeling the tension in my shoulders begin to melt away. “They say they don’t take colored hair, but my hair is really strong and it was super long, so I sent like 20 inches off in case they could turn it into a wig or something.”

  It was the most I had said in hours . . . maybe days. Something about this girl allowed me to relax. I didn’t feel like I needed to be on guard and I could sense that she genuinely wanted to be my friend.

  “Oh, that’s so sweet! I’ve always wanted to do that,” she cooed before sticking her hand out in front of me. “I know we’ve met before, but I’m Bridget.”

  “I’m Holly,” I said, a smile taking over my face. “It’s really nice to meet you again.”

  Bridget started popping up around the mansion pretty regularly after that. Much to my surprise, she was just another girl invited to spend time at the mansion; her cheerfulness wasn’t an act and she wasn’t being paid to promote a brand, as I had initially assumed. She didn’t have that same desperate air about her that plagued most of the girls who frequented Hef’s place. Plus, she wasn’t another platinum, plastic wannabe: this girl was refreshingly natural. She had dark blond hair, natural makeup, was plastic surgery free, and was always outfitted in some sort of themed ensemble. She was a walking, talking candy cane and I liked having her around. In a way, she reminded me of myself before Hef and his girlfriends had completely stripped me of my confidence.

  It wasn’t long before we became best friends. Her energy was contagious, making it nearly impossible to ever be in a bad mood when you’re with her. Plus, it was a welcome relief to have a new friend in the house.

  Eventually, Bridget Marquardt became one of Hef’s girlfriends. When she moved in, I had already been at the mansion for more than a year and had been witness to the comings and goings of quite a few girlfriends. But for once, I didn’t mind a new face taking up residence.

  Looking back, I often wonder if having a friend like Bridget earlier might have saved my sanity. If I had had anyone else to turn to besides Hef, maybe I would have been able recognize the situation for what it was instead of convincing myself to fall in love with him.

  CHAPTER 5

  Alice thought the whole thing very absurd, but they all looked so grave that she did not dare to laugh.

  —Lewis Carroll, Alice’s Adventures in Wonderland

  Over the year I lived with her at the mansion, Vicky became increasingly hostile. She wanted desperately to be a Playmate, but Hef was done making girlfriends centerfolds—only we didn’t know that then. Hef still let the possibility linger, knowing it was the key to attracting and keeping countless young girlfriends. Earning Playmate status became Vicky’s obsession. A new crop of girls had moved into the mansion over the past year and Vicky was hell-bent on beating this new group to the coveted title. It seemed to me that she felt her seniority in the group gave her an edge or made her an exception when it came to snagging herself a centerfold.

  “If he’s not going to give me a centerfold, I’m at least going to get everything I can out of this place,” Vicky fumed in my general direction. She had invited me to her room to “talk,” something we hadn’t done since my earliest days at the mansion. After Lisa became a centerfold and moved out a few months earlier, Vicky moved up into one of the largest of the rooms designated for girlfriends.

  I watched as she stumbled around the large pink room, trying to avoid tripping over the piles of junk she’d amassed in every corner, including those covering a long white couch that had occupied the room since the ’80s. She motioned that I grab a seat on her bed, but I was unsure how to navigate the journey. I was fairly certain that this particular room had plush white carpeting, but you couldn’t see the ground anywhere. Random trinkets, mementos, and tchotchkes were scattered about: a skateboard collection, a wall full of Barbie dolls still in their original packaging, an oversize aquarium, a Ping-Pong table covered with Hello Kitty merchandise, an oversize disco ball, and a stable of inflatable unicorns.

  I mean, I love me some camp, but this was enough to make Angelyne cringe. If “getting everything she could out of this place” meant becoming a hoarder, than she was succeeding with flying colors (many of which were shades of pink).

  I noticed that she had a piece of paper taped over a vent on the wall. “What’s that?” I asked.

  Vicky looked over her shoulder.

  “Oh, that?” she asked, pointing towards the vent.

  I nodded.

  “The girls who were in here last night put that up,” she nonchalantly explained. “They were up here smoking meth and it has this like, really foul smell, like rotten eggs, so they covered up the vent.”

  I nodded again, hoping the shock and amusement wasn’t readable on my face.

  “They knew if the smell made its way down to the butler’s pantry, someone might figure it out and bust ’em,” she continued.

  “Huh,” I said, going through a mental Rolodex of her girlfriends to figure out which ones she was talking about.

  “Speaking of the other girls . . .” Vicky began, a new focus in her voice. “You know I can’t stand Dianna, right?”

  “No, I didn’t,” I replied. How would I know who was on Vicky’s list of enemies?

  At the ripe old age of 29, Dianna was one of the oldest in this new crop of girlfriends. She was beautiful, but there was something a little off about her. She had wild, violent mood swings and looked more like an attractive 40-something with a face full of Botox and fillers than a 29-year-old.

  “Okay. Well, you know how when you do coke, there’s like a pile in the center with some lines next to it for people to do?” She paused. It took me a second to realize she was waiting on me to respond. Quickly I nodded. I didn’t do it myself, but I’d been offered cocaine countless times since moving in—it was definitely the drug of choice among the girls of the mansion.

  Apparently satisfied with my response, she continued: “Well, Dianna doesn’t do the lines . . . she does the whole fucking pile!” Her eyes were wild as her arms flew in the air. “It’s like, bring your own shit.”

  I wondered if Vicky was high this very moment. It would explain her spastic behavior and even why she invited me into her room in the first place.

  “You know Amanda, that new Playmate?” she asked, jumping to the next subject without missing a beat.

  I actually had an answer for this one!

  “Yes!” I exclaimed. I’d only met Amanda a handful of times while she was shooting her pictorial, but the wholesome dark-haired beauty definitely left an impression. She possessed an air about her, like she just walked off the pageant stage. I always noted her impeccable manners—a rarity in the Playmate world. “I really like her. She’s so pretty and seems really classy.”

  “Well, she’s not!” Vicky whirled around with a huff. Apparently that was the wrong answer, because Vicky unleashed her Amanda-focused tirade. “You know, don’t you ever wonder, for a girl to want to pose nude, there has to be something wrong with her, right?”

  I kept my mouth shut. Her eyes narrowed on me as she waited for my response. It seemed like a loaded question, since both Vicky and I were eager to become Playmates. I thought she might be getting to some sort of point—perhaps whatever it was that motivated her to ask me to her room in the first place.

  �
�Well, she makes a lot of money,” Vicky finally said, her claws momentarily retracted. “Like, thousands of dollars a night. Actually, almost all of the Playmates make that kind of money.”

  Vicky paused, waiting for me to take the bait and ask how they made that kind of money. She took a seat on top of what appeared to be a small mound of dirty clothes on the white couch and began casually petting the tiny dog that had crawled into her lap. After it was clear I wasn’t biting, she continued her story on her own.

  “Take Carrie, for example . . .” she continued, her eyes on the little animal.

  A recent Playmate, Carrie was a 21-year-old with a 16-year-old face. She had striking green eyes, but no personality. I remembered seeing her a few days earlier at the Fun in the Sun party droning on about her swimsuit.

  “Do these look like pumpkins,” she had asked Vicky, stretching her orange-dotted Dior bikini over her chest.

  Wow, I remembered thinking. Playmates must make some pretty good money to be able to afford Dior bikinis.

  “Well,” Vicky continued, snapping me back to the present, “she has a lot of sugar daddies. One pays for her apartment, one pays her bills, one takes her shopping . . .”

  “No way!” I shouted, unintentionally cutting Vicky off. Rumors of Playmates working for “high class” escort agencies had plagued Playboy for decades, but it wasn’t common knowledge and I’d never heard of it firsthand before.

  “Yeah,” Vicky said with a carefree laugh. “And everybody does it.”

  And as casually as if she were inviting me to tea, she asked: “Do you think it might be something you’d be interested in?”

  “No way!” I said, almost laughing. Was she really asking me if I’d consider becoming a hooker!? Sure, I’d made a bad decision moving into the mansion, but I wasn’t down for full-on prostitution. She wasn’t going to get me this time.

  My eyes fell on Vicky and I quickly adjusted my expression. I couldn’t be certain, but I was fairly sure our newly rekindled friendship would be short-lived. “Umm, I mean,” I sputtered, uselessly trying to recover, “that’s just not something I’m into.”

  Her face was starting to morph from terribly offended to wildly angry. I kept talking, hoping it would stave off the shit storm I just walked into.

  “I mean, it’s just a little much for me, there’s nothing special about it,” I floundered, trying in vain to come up with anything that might not piss Vicky off. I could feel the blood pumping in my cheeks, certain I was bright red. Vicky had just opened the door to her secret little world and I slammed it in her face.

  “Okay, whatever,” she spat. “Hey, I need to get ready, so I’ll see you later, okay?”

  “Okay,” I said, recognizing that it was my cue to leave.

  Oh my god, I thought, I can’t wait to tell Bridget about this!

  I came to believe that Vicky was working for Hollywood madam Michelle Braun (the owner and operator of the high-end escort service Nici’s Girls). In the late 1990s and early 2000s, “Nici” was the premier madam who prided herself on a reputation of having the most exclusive girls in the business—many of which were Playmates and even some of Hef’s own girlfriends.

  In a 2009 New York Post article, Braun boasted, “at one time, seven of the eight girls living in the Mansion were working for me. I had one of his girlfriends in the Mansion just to recruit for me.”

  When I read this article, it was obvious to me that Vicky must have been her recruiter. I compared notes with a few of the other girlfriends and found that they had also been approached by Vicky. One of the girls said Vicky had confided in her that she got a cut or fee for the girls she was able to introduce to Braun. Girls were routinely convinced that these men were willing to pay a premium for simply the pleasure of their company and not necessarily for sex—but, from what I understand, that was almost never the case. While I was at the mansion, there were a handful of girlfriends who refused the invitation to hook (Bridget was never even approached), but I have no idea what went on before I got there.

  A few years ago, Braun’s client and employee list, circa 1999, surfaced on the Web (gossip site HollywoodInterrupted.com published the documents). Among the many notable names were Hef’s former girlfriends Mandy and Sandy Bentley, as well as his former main girlfriend Tina Jordan. (In 2009, Braun was indicted after pleading guilty to transporting women across state lines for the purpose of prostitution and money laundering and was sentenced to three years’ probation and six months of house arrest.)

  The women were tempted with the lavish life that a $1,000 weekly allowance certainly wouldn’t provide for. They would travel all over the world and make upwards of $25,000 to spend an evening with whoever was willing to shell out the cash. Girls were making money hand over fist! They became addicted to L.A.’s opulent lifestyle—expensive cars, designer handbags, luxury apartments—and sadly, for many of these women, the majority of their income went to supporting some pretty nasty drug habits.

  At the end of the day, whatever their reasons for making this choice, I never judged them—and I certainly don’t now. Vicky, however, disgusts me. If she was indeed Michelle Braun’s recruiter, then she preyed on the young, naïve women who tumbled into L.A. with stars in their eyes, and used them for her own gain.

  In 1997, ’80s Playmate Rebecca Ferratti made headlines when she participated in an E! True Hollywood Story titled “The Sultan and the Centerfold.” Ferratti recalled her spiral into the world of prostitution. In her day, high-end call girls were being shipped off to Brunei to meet their clients. In the early 2000s, Turkey was the hotspot for these L.A.-bred escorts.

  Braun said during a 2008 Rolling Stone interview that her big break in the escort business was landing Turkish billionaire Hakan Uzan as a Nici’s Girls client (the article named Playmate Tishara Cousino and Playboy cover girl Ashley Massaro as employees, as well as Tina). “Hakan would send me an instant message at 3 A.M., and I would have to get four Playmates ready right away,” Braun told the magazine. “The first flight to Istanbul was around 6 A.M. through Paris, and sometimes I’d wake them up in the middle of the night for that flight.”

  The madam was arrested in 2007 and revealed details about her global hooking empire during the Rolling Stone interview, but Playboy—and Hef—had known about the racket for years. In fact, Hef even launched his own private investigation into the matter in hopes of shutting down Nici’s Girls and other agencies standing on the shoulders of the Playboy name. The hypocrisy here is palpable. Considering Hef kept his own “harem” of sorts, it’s easy to see the mansion as a gateway to hooking. But Hef was determined to plug this leak—not necessarily for the benefit of the girls, I believe, but to maintain Playboy’s image. It wouldn’t look that good if a majority of Playmates graduated to sex for pay. Playboy was supposed to be “classy,” after all.

  Eventually, I learned more about the situation from Mary O’Connor, who had become a close friend. During my morning visits to her office, I would hear about the goings-on and frequently come across documents pertaining to the investigation. Instinctively, I grabbed a stack of contact sheets off Mary’s desk, thinking it had to be negatives from the newest Playmate test shoot—something I always pored over.

  My heart sank when I saw what the images actually were. In the photos was a red-faced, swollen-eyed Playmate, one that I knew well. Wearing a hot pink wig, looking like she was drugged out of her brain, posing nude for the unknown photographer, she was subjecting herself to the most repulsive and demeaning positions. She was showing parts of her anatomy never even seen in the pages of Playboy; in fact I’m not sure you’d even see some of this in Hustler. In her drug-fueled state, she must have thought the hot pink wig would sufficiently mask her identity . . . despite her face being very clearly on display.

  Hef was determined to put an end to the Playboy prostitution ring—still unaware he had an enemy under his own roof—and put new restrictions in place to better ensure that his centerfolds weren’t participating in Nici’s Girls
.

  If he found out that one of his Playmates had been associated with this ring, that person would be stripped of any Playmate responsibilities. (I don’t even think he considered that any of his girlfriends had been participating.) As soon as word of these new restrictions started circulating, it didn’t take long for girls to start panicking.

  “Holly, I need your help,” the breathless caller squeaked through the splotchy connection.

  As 2002 was nearing its end, it was time for Hef to select Playmate of the Year. Amanda was in close contention with a handful of other girls, and I was not so quietly rooting for the fresh-faced beauty. I thought she was warmer and friendlier than most of the other candidates and would make a good representative for the magazine.

  While Amanda and I had met a few times, we were by no means close, so when one of the mansion butlers rang my room from the pantry switchboard to tell me Amanda was on the line, I was surprised.

  “Sure, what do you need?” I said. I figured she wanted me to put in a good word with Hef about her candidacy. People always thought I had a lot more leverage than I did.

  “I need you to talk to Hef,” Amanda begged, sounding desperate. “They told me I was getting Playmate of the Year, but now they’re saying they aren’t going to give it to me.”

  Immediately, my conversation with Vicky months earlier popped into my head.

  “Why?” I asked, hearing my own trepidation.

  “They asked to see my passport,” she explained urgently. “And I don’t have it.”

  “Why do they want to see your passport?” I asked, already suspecting the answer.