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'Sleep With Donald Trump', The Competition We All Missed in 1990

Updated: Jul 7, 2022

In August 1990, Playgirl Magazine advertised the chance to “Sleep with Donald Trump” on its cover to its predominantly female audience.

The move followed Trump’s messy and public divorce with his first wife, Ivana, who alleged that the entrepreneur had sexually assaulted her and pulled out her hair. Ivana Trump reportedly walked out of the marriage with a settlement of between US$14 million and US$25 million.

As his divorce pended, the magazine quickly ran a contest with the offer to “sleep with” the businessman. “He’s rich, almost single and yours for the asking,” a blurb on its table of contents read. “Here’s how you can get the Donald out of your dreams and into your bed!”

Obviously, readers weren’t actually invited to get frisky with Trump. According to fact-checking site Snopes, the contest was simply a PR stunt approved and paid for by Trump and/or a book publisher which explained, in the small print, that winners would receive a pillowcase silk-screened with an image of his face.

The description also touted Trump as a fitting bedfellow by stating, “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.’” As well as a pillowcase made for audiences to “lie there whispering sweet nothings to his ear all night,” winners would each be handed a copy of Joel Reed’s Donald Trump: The Man, The Myth, The Scandal. “Don’t wait,” Playgirl magazine prompted. “A catch like Donald Trump won’t stay out of someone’s bed for long!”


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