Playgirl Ran a ‘Sleep with Donald Trump’ Contest in 1990?

For years, claims have spread across social media platforms that Playgirl magazine ran a “Sleep with Donald Trump” contest in their August 1990 edition.

An X (formerly Twitter) post from 2023 stated, “That one time #Trump was in Playgirl for anyone to win a trip to his bed.” Attached were four images that allegedly showed the contest in question.

We found posts about the claims on other social media platforms, including TikTok, Reddit and Instagram.

Playgirl did run a “Sleep with Donald Trump” contest, as we previously reported in 2020. We reached out for further details to Playgirl, which confirmed the magazine had run the contest in its August 1990 edition, as well as in the “Coming Up” section in its July 1990 issue.

As we reported in 2020, Trump and his first wife Ivana were in the midst of their divorce around the time the photo contest was announced. The contest claimed it picked 25 winners, one for “each million of soon-to-be-ex-wife Ivana’s prenuptial agreement.” (The New York TImes reported in 1991 that she received $14 million in the divorce settlement.)

The prize for winning the contest was a pillowcase with Trump’s face on it, as well as a copy of “Donald Trump: The Man, The Myth, The Scandal” by Joel Reed:

He’s tall, good-looking, about to be divorced, and rich beyond your wildest imagination. His every move makes headlines — even his bedroom moves One woman reportedly called him “the best sex I’ve ever had.” He’s multi-billionaire Donald Trump, and now, if you win our contest, you can snuggle up and get to know him too.

It’s easy! Just fill out the coupon below, and mail it in to us by August 15, 1990. We’ll pick 25 winners at random (one for each million of soon-to-be-ex-wife Ivana’s prenuptial agreement).

Each lucky winner will receive a pillowcase exclusively silkscreened for this PLAYGIRL contest with the Donald’s face, so you can lie there whispering sweet nothings in his ear all night. If you win, you’ll also get a copy of Masquerade Books’ hot new read, Donald Trump: The Man, The Myth, The Scandal, by Joel Reed. You’ll be able to find out whatever you want to know about America’s most magnetic magnate.

Don’t wait. A catch like Donald Trump won’t stay out of someone’s bed for long!

The magazine wasn’t able to provide us with any further information about the winners of the contest.

We’ve previously reported on claims that involve Trump and other magazines, including the allegation that the former president once told People magazine that “Republicans are the dumbest group of voters.”