In 2006, Donald Trump‘s reality show The Apprentice had only been on the air for two years, but everyone already knew it was a hit.
Anyone looking for a springboard to fame or a rejuvenating shot in the arm of a flagging career wanted a piece of it.
NBC was hosting a party for the production at The Playboy Mansion in Beverly Hills, California – and in the crowd was a bombshell brunette wearing a see-through dress over her swimsuit.
Her name was Karen McDougal.
On several occasions since that night, McDougal, now 53, has recounted the events of that evening and the alleged whirlwind romance with a future president that followed.
She even claimed that Trump once confided in her that he had actually turned to his son Eric that night and asked, ‘Who is the most beautiful girl here?’
Eric – apparently – pointed her out and within a few days, according to McDougal, she and Trump were alone together in his private bungalow at the Beverly Hills Hotel.
‘We talked for a couple [of] hours – then, it was «on!» We got naked and had sex,’ she wrote to a friend in a letter later leaked to the New Yorker.
NBC was hosting a party for the production at The Playboy Mansion in Beverly Hills, California – and in the crowd was a bombshell brunette wearing a see-through dress over her swimsuit. Her name was Karen McDougal (Above, center).
On several occasions since that night, McDougal, now 53, has recounted the events of that evening and the alleged whirlwind romance with a future president that followed.
Now McDougal finds herself thrust back into the public spotlight as Trump faces 34 felony counts for allegedly falsifying business records to cover up a purported affair with another woman – porn star Stormy Daniels.
Unlike Trump’s alleged fling with Daniels – who once described the tryst as ‘the worst 90 seconds of my life’ – McDougal has insisted that they were in love and she thought they would one day marry.
But despite those tender feelings, in 2016, as Trump was waging a political campaign, Ms. McDougal decided it was time to tell her story – and allegedly asked a lawyer to sell it to a supermarket tabloid.
In a Manhattan courtroom on Monday, the prosecution’s star witness and former Trump attorney Michael Cohen testified that he helped arrange the transaction.
The jury heard an audio recording that Cohen secretly made of himself briefing Trump in September 2016 about his plan to reimburse National Enquirer publisher David Pecker for buying McDougal’s tale, which began – improbably – in small-town America.
One of five children, McDougal was born in Merrillville, Indiana but spent her childhood in Sawyer, Michigan, where she excelled at tap dancing and cheerleading and became a state champion clarinet player four years in a row.
In high school, her wholesome nature earned her the nickname ‘Barbie.’ But all the accolades and girl-next-door looks apparently weren’t enough.
‘I think, like every girl, I wanted to enhance my appearance and I wanted my chest to be bigger and feel more womanly,’ she said years later.
In 1996, at 22 years old, McDougal underwent surgery to enhance her breasts from 34B to 34D.
In a Manhattan courtroom on Monday, the prosecution’s star witness and former Trump attorney Michael Cohen testified that he helped arrange for the National Enquirer to purchase karen McDougal’s story.
In high school, her wholesome nature earned her the nickname ‘Barbie.’ But all the accolades and girl-next-door looks apparently weren’t enough. (Above) Karen McDougal during 7th Annual Playboy Golf Scramble Championship Finals at Lost Canyons Golf Club in Simi Valley, California
In recent years, McDougal has become a spokesperson for ‘breast implant illness.’ The condition is not medically recognized, but McDougal says it led to her decision to have her implants removed in 2017.
After graduating from Ferris State University with a degree in elementary education, McDougal went on to teach pre-kindergarten in a suburb outside of Detroit.
Then a friend persuaded her to show off the voluptuous new figure in a local swimsuit contest.
McDougal came in first. And life changed forever.
From the regional competition, she went on to a national showcase in Florida – and it was there that she was discovered by a scout for Playboy Magazine.
She made her Playboy debut as ‘Miss December 1997’ with a fully nude outdoor photoshoot taken in the snowy fields of Park City, Utah.
While many men claim to have Playbook subscriptions ‘for the articles,’ they certainly couldn’t have professed to have gained any great insights from McDougal’s spread.
‘I love cats, they have a definite attitude,’ she mused in a flirty baby voice for the 1997 interview. ‘They allow us to feed them and pet them in exchange for letting us enjoy their presence. I never heard of a cat with a lack of self-esteem!’ she said.
In another revealing moment, McDougal divulged that despite being a natural in a bikini she was afraid of the water and didn’t know how to swim.
Regardless, Playboy readers believed this rising star had what it took.
She won ‘Playmate of the Year’ in 1998 and was awarded $100,000 along with a special edition silver Ford Shelby convertible with a customized license plate that read ‘PMOY 98.’
In 1999, she became the first woman to appear on the cover of Men’s Fitness magazine, landed small acting roles in the 2000 film Charlie’s Angels and the 2001 cult flick Gladiatrix, and magazine buffs voted her runner-up for ‘Sexiest Playmate of the 90s’ behind iconic former Baywatch babe Pamela Anderson.
Then, suddenly, the opportunities seemed to dry up.
From the regional competition, she went on to a national showcase in Florida – and it was there that she was discovered by a scout for Playboy Magazine. (Above) Karen McDougal (third from right with Hugh Hefner)
McDougal won ‘Playmate of the Year’ in 1998 and was awarded $100,000 along with a special edition silver Ford Shelby convertible with a customized license plate that read ‘PMOY 98.’
McDougal signed a contract with World Wrestling Entertainment (WWE) and advanced to the last stages in WWE Diva Search, a talent competition to become a female wrestler. She didn’t make the final cut.
Around this time, McDougal found herself back at the Playboy mansion – and her path crossed with Donald Trump.
After their chance meeting at the Hugh Hefner’s estate, McDougal said she and Trump had their first date at the Beverly Hills Hotel.
She was apparently shocked when Trump’s bodyguard allegedly drove her through the back entrance of the compound to Trump’s room for dinner.
They had steak and mashed potatoes in the kitchenette while the television played in the background.
After the meal, McDougal says they had sex.
It would have been two days before Trump’s 60th birthday. McDougal would have been 35 years old at the time.
And the night, unfortunately, ended in tears.
McDougal said Trump offered her money. ‘I’m not ‘that kind of girl,» she claimed to have told him.
Trump – she says – responded by telling her she ‘was special.’
They allegedly continued to hook up in hotels, at Trump golf courses in New Jersey and California, and his home in Bedminster, New Jersey. He purportedly even took her to his gold-laden, three-story penthouse in Trump Tower in Manhattan.
McDougal said Trump offered her money in exchange for the sex. ‘I’m not ‘that kind of girl,» she claimed to have said. Trump – she says – responded by telling her she ‘was special.’ (Above) Donald, Melania and Ivanka Trump pictured with Karen McDougal (far-right)
Today, McDougal is a born-again Christian splitting her time between Arizona and Los Angeles.
‘As we passed staff in the building, I asked: «Aren’t you afraid they’re going to say something?» And Trump said «nah, they won’t say anything,»‘ she remembered.
Trump was said to have paid her the ultimate compliment by comparing her to his beloved daughter, Ivanka. ‘He said I was beautiful like her and, «You’re a smart girl,»‘ McDougal claimed.
But by April 2007, the bloom was off the rose.
McDougal insisted that she decided to call it quits over alleged derogatory remarks made by Trump.
According to her private note that was given to The New Yorker, she and a friend were with Trump in a limousine when he reportedly suggested that the friend, who was dating an African American man, liked ‘big black ****.’
It was really over, McDougal told DailyMail.com in 2023, when Trump allegedly called her mother an ‘old hag.’
By this time, McDougal had already begun speaking to Hollywood superstar, Bruce Willis, whom she met at a Los Angeles nightclub.
Hot off his divorce from Demi Moore, Willis was pictured hand-in-hand with McDougal on holiday in Italy in August 2007.
They broke up six months later.
‘I wasn’t cheating on Trump but Bruce and I were talking on the phone a lot already so that made it easier to end it,’ she told DailyMail.com. ‘Why would I stay with a married man when Bruce was a nice guy, and single?’
Hot off his divorce from Demi Moore, Willis was pictured hand-in-hand with McDougal on holiday in Italy in August 2007.
‘I wasn’t cheating on Trump but Bruce and I were talking on the phone a lot already so that made it easier to end it,’ she told DailyMail.com. ‘Why would I stay with a married man when Bruce was a nice guy, and single?’
In recent years, McDougal has become a spokesperson for ‘breast implant illness.’
The condition is not medically recognized, but McDougal said it led to her decision to have her implants removed in 2017.
‘I got to the point where I had no life and I literally thought I was dying,’ she told PEOPLE Magazine. ‘In October 2016, I was on bed rest. I couldn’t drive, I was having panic attacks, I couldn’t see. I had hearing sensitivity, I couldn’t stand noise, I couldn’t tolerate light, I had joint pain, brain fog.’
Today, McDougal is a born-again Christian splitting her time between Arizona and Los Angeles.
‘He was in love with me. I know that because he told me all the time. He’d say «You’re my baby and I love you,»‘ she said of Trump.
‘There were real feelings between the two of us,’ she continued. ‘What everyone sees on TV, I didn’t see in that man, because that man was very sweet, very respectful, very loving, very kind, and very caring.’
It’s not clear how McDougal feels today about her story being used to attempt to put her alleged former paramour in prison.
DailyMail.com has reached out to McDougal’s representatives for comment, but has not received a response.
