From Playboy superstar to secret lover of a future president,
here's the truth about Trump's alleged former mistress, Karen McDougal.
Karen McDougal was born in Indiana in 1971 and grew up in rural Michigan as the fourth of five
children. In addition to the number of athletic and artistic activities she took up in school,
her sweet demeanor and beauty earned her the nickname "Barbie."
After high school, McDougal attended college for two years at Ferris State University before
departing to a suburb of Detroit to work as a preschool teacher — and she may have stayed
in that lane indefinitely had it not been for a friend convincing her to enter a swimsuit contest,
which led to an opportunity to begin competing internationally.
During one of the international competitions, McDougal met a photographer affiliated with
Playboy, a connection which encouraged her to move to California for a test shoot with
the magazine. She didn't know it yet, but as soon as she set foot in the Playboy
Mansion for the first time, she was launching a lucrative and highly successful new career.
Growing up, Karen McDougal had dreams of her own but never could she have imagined that someday,
she would be posing for Playboy magazine, revealing in her Playmate interview -
"I was always wholesome little Karen. [...] That sort of girl isn't expected
to be seen in the most-looked-at men's magazine in the world."
But as the saying goes, life is full of surprises. Two days after her first
test shoot for Playboy, McDougal got the call booking her for her first
professional photo spread in the magazine. Soon after she began working with Playboy,
she was crowned Miss December 1997. Writing on her website, McDougal said -
"It all happened very fast. I honestly didn't think that I was going to be
accepted considering that Playboy has tens of thousands of girls apply every year."
Thanks to a large number of votes earned through call-ins, write-ins, and Playboy TV,
McDougal became the magazine's 1998 Playmate of the Year. By 2001, she had become so popular
through her evocative photo spreads and promo work that she was voted the number 2 Playmate
of the '90s by the magazine's readership, bested only by superstar Pamela Anderson.
Modeling might have been her first love but Karen McDougal was not one to be confined in a box. In
2001, McDougal's career took a detour into acting when she starred in the Roger Corman-produced
B-movie "The Arena," playing a Roman slave who becomes a gladiatrix named Jessemina. Though
"The Arena" remains her biggest movie to date, the model also snagged a few more uncredited
appearances in films, and a brief speaking role came in the series "Anger Management. "
"How do you do?" "Did you just curtsy?"
"A little."
When her acting career didn't garner as much success as expected,
McDougal also tried her hand at reality TV. In 2004, McDougal was one of the 28 finalists
that contested for WWE Diva Search, a talent competition organized and produced by WWE,
where she was eliminated in the semi-finals. In her heyday, the former model also tried
her hand at hosting various things, from Red Carpet events to the World Series of Poker.
She might not have been able to talk about her alleged relationship with Donald Trump
as much as she would have liked, but Karen McDougal always had a friend in her diary,
where she documented their reported affair. McDougal's diary would later be used in a 2018
New Yorker exposé written by journalist Ronan Farrow. As reported by the outlet,
Trump and McDougal met in 2006 during a party for "The Apprentice" at the Playboy Mansion
where he asked for her cellphone number. By their supposed interaction that night,
it did not take much to see that the business mogul was interested in pursuing a relationship
with McDougal, who wrote in her diary - "It was so obvious that a Playmate Promotions
exec said, 'Wow, he was all over you — I think you could be his next wife."
But what seemingly started as a fling soon reportedly evolved into
a months-long affair which McDougal claims was more than just a physical relationship.
"There was a real relationship there. There was a, there were real feelings between the two of us,
not just myself, not just him. There was a real relationship there."
After their supposed first date, Karen McDougal and Donald Trump reportedly started seeing
each other often, with most of the meetings happening whenever the Mar-a-Lago owner was
visiting Los Angeles. Soon enough though, the pair graduated to attending public events together,
with Trump allegedly funding all of McDougal's trips. But even though
Trump was more than happy to take care of the bills, he was also sure to do it with
utmost secrecy. According to a report from The New Yorker, McDougal wrote in her diary -
"No paper trails for him. In fact, every time I flew to meet him,
I booked/paid for flight + hotel + he reimbursed me."
Their travels took them to California, where the future President reportedly did his best
to keep her away from the orbit of pro golfer Tiger Woods, another notoriously unfaithful
public figure. Apparently, Trump specifically warned her to stay away from the golf star.
Karen McDougal and Donald Trump reportedly began seeing each other with what she described as a
first date at the Beverly Hills Hotel, with Trump favoring one bungalow that they would
allegedly return to often. According to her diary, McDougal saw him whenever he came to LA,
and she made several observations about Trump in her writings during this time,
including that he was supposedly a man who stuck to habit. According to McDougal,
he would always order steak and mashed potatoes when they ate. But while she
enjoyed the time together, he seemed to view their relationship as transactional.
"After we had been intimate, he tried to pay me, and I actually didn't know how to take that."
McDougal claimed that she didn't see their relationship that way at all,
writing in her diary -
"After, we got dressed to leave. He offered me money. I looked at him [...] and said,
'No thanks — I'm not that girl.' I slept with you because I like
you — NOT for money.' He told me 'you are special.'"
In hindsight, the gesture may make sense. At the same time that Trump was reportedly seeing
McDougal, he was also allegedly carrying on affairs with several other women.
Karen McDougal claimed that during their alleged affair,
she paid multiple visits to Trump Tower in midtown Manhattan. There,
she noted in her diary that Melania Trump had a separate bedroom. At the time, Donald Trump and
Melania had been married for less than two years, with McDougal writing in her diary -
"He did take me to his house — showed me around. Pointed out
his wife's bedroom. Said she liked her space — to read or be alone sometimes."
This wasn't the only uncomfortable moment she reportedly had with Trump's family.
According to McDougal, Trump had a habit of frequently remarking on similarities he saw
between herself and his daughter Ivanka, sending her articles about himself or his
daughter and showing off her appearances on magazine covers. McDougal's encounters
with Trump's sons were more muted. She says she sat with Donald Trump,
Jr. and his wife during an event for Trump Vodka. She also supposedly had an encounter with Eric
Trump during a party for "The Apprentice" held at the Playboy Mansion, writing in her diary -
"I was working as a 'Bunny' that night. [Donald's] whole family was there. We took
pics together alone and with his family. He told me he asked his son, Eric, who he thought was the
most beautiful girl here and Eric pointed at me. Mr. T said 'He has great taste' and we laughed!"
Karen McDougal ended her relationship with the real estate mogul after nine months, supposedly
unable to get beyond feelings of guilt about intervening in his marriage. According to her
friend who provided her diary to The New Yorker - "She couldn't look at herself in the mirror
anymore, and she was concerned about what her mother thought of her."
McDougal raised her concerns about their alleged affair to Donald Trump,
particularly the one about her mother's disapproval, to which Trump allegedly replied -
"What, that old hag?"
This, among other inflammatory comments about gender and race supposedly offended
McDougal to the point where she finally felt comfortable breaking off the relationship.
Today, she reportedly regrets the affair, telling The New Yorker that upon looking back, she would
do things differently. McDougal says that she came forward about the affair to add her voice
to the chorus of other women who are standing up to showcase the abuses made by high-profile,
powerful men. As The New Yorker piece notes, several of the women Trump has
allegedly had affairs with have accused him of sexual assault, with McDougal saying -
"I know it's a different circumstance,
but I just think I feel braver. Every girl who speaks is paving the way for another."
In November 2016, only a few days before the Presidential election, The Wall Street Journal
published an exposé revealing that Donald Trump pulled some strings to prevent the story of his
affair with McDougal from becoming public. According to the article, McDougal was at
some point attempting to sell the story of their alleged affair when Trump and his friend David
Pecker, then CEO of American Media Inc. also known as AMI, caught wind of her plans. To contain the
situation, The National Enquirer, a subsidiary of AMI, subsequently reached out to McDougal,
striking a non-disclosure agreement deal to pay $150,000 in exchange for the story. In addition
to the $150,000, McDougal was reportedly also offered two cover page features as well as a
column in the magazine's wellness section — a contract that was only partially fulfilled.
Given the NDA clause in their agreement, McDougal was for a long time unable to publicly discuss her
alleged affair with the former president, admitting to The New Yorker in 2018 -
"It took my rights away. At this point, I feel I can't talk about anything without getting into
trouble, because I don't know what I'm allowed to talk about. I'm afraid to even mention his name."
Though McDougal was eventually freed from the contract in 2018,
she has since retired from the spotlight, seemingly enjoying life away from the Trump drama.