Hollywood Flashback: Donald Trump Tried to Topple the NFL in the 1980s

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Donald Trump (right) and New Jersey Generals coach Walt Michaels at Giants Stadium in 1983.

Andy Warhol helped judge the future president's cheerleader competition for his USFL team, and the two later had a failed collaboration over the artist's paintings of Trump Tower.

Perhaps Donald Trump's most creative innovation as a United States Football League team owner was having Andy Warhol choose its cheerleaders.

In 1983, the future president, then 37, paid $9 million for the New Jersey Generals — part of a startup league seeking to become a springtime alternative to the NFL. "The only reason Donald bought a USFL team is he wanted an NFL team and was not invited into their exclusive club," says Mandalay Sports Media co-chairman Mike Tollin, who made a documentary on the USFL.

To generate publicity, Trump held a cheerleader competition in Manhattan's Trump Tower basement with a jury that included impressionistic painter LeRoy Neiman, opera singer Beverly Sills and Warhol, who watched dozens of young women strut to Michael Jackson's "Billie Jean." Warhol had met Trump two years earlier at a birthday party for attorney Roy Cohn, and Trump visited his Factory. The artist, who in his Diaries calls Trump "a butch guy," created on spec eight 50-by-42-inch black-and-silver silk screens of Trump Tower for the building's lobby, then still under construction.

But the collaboration did not go well. "It was a mistake to do so many," Warhol wrote. (Trump also wanted the paintings in pink and orange.) "I think Trump's sort of cheap though. I get that feeling." Trump didn't buy them, and two now belong to the Andy Warhol Museum in Pittsburgh.

As for the USFL, it didn't fare much better, only lasting three years. A plan that Trump favored was to move its season from spring to autumn, try to force a merger with the NFL and, if that failed, have Cohn file a $1.32 billion anti-trust lawsuit against the dominant league. In a baroque way, it both worked perfectly and failed disastrously: The USFL won the lawsuit, but the jury awarded just $1 in damages (which Trump called "a moral victory"). The USFL folded, and the $3.76 settlement check (it included interest and triple damages for the anti-trust aspect) from the NFL, which is holding its 51st Super Bowl in Houston on Feb. 5, never has been cashed.

This story first appeared in the Feb. 10 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.