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Back in 1990, businessman Donald Trump — although already famous by some measure — possessed a much lower public profile than he does today. In ensuing years, events such as the publication of multiple books by and about him, the success of the television show The Apprentice, and his entry into U.S. politics would multiply his level of national (and international) fame many times over. But perhaps the single thing Donald Trump was most famous for at the beginning of the 1990s was his messy divorce from his first wife Ivana, which played out across the headlines of New York tabloids. Amid Ivana's claims of cruel and inhuman treatment at the hands of Donald, and Ivana's accusations that Donald had raped her and pulled out her hair by the handful, the couple eventually reached a divorce settlement that reportedly left Trump's ex-wife with anywhere from $14 million to $25 million. Against the backdrop of this very public divorce, the August 1990 issue of Playgirl magazine (a publication intended to emulate the success of Playboy magazine but with a female audience) teased its readers with a cover blurb that stated Sleep with Donald Trump: The magazine's table of contents offered a blurb for the Sleep with Donald Trump contest that proclaimed: He's rich, almost single and yours for the asking. Here's how can you get [sic] the Donald out of your dreams and into your bed!: The underlying contest — which was quite likely a PR effort coordinated and paid for by Trump himself and/or a book publisher — turned out to be little more than deceptive wordplay, full of flattering remarks about the Donald (even if they were invented ones) and catty references to his divorce. Readers quickly learned that the only prize to be won in this contest was a pillowcase with Trump's face silk-screened onto it: Unfortunately, history has not left us a record of the reactions of the contest's winners (if indeed there actually were any).
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