Down the Rabbit Hole - Holly Madison

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.
“I don’t know,” she lied.
“Well, where is it?” I felt like I was interrogating her, but it was clear she was trying to
manipulate my position. If Hef knew she was a prostitute, I couldn’t very well campaign for her as
Playmate of the Year.
“I left it at my mom’s in Washington,” she cried. I could hear the panic in her voice. Her dreams