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Donald Trump in His Youth: Rare Photos From His Childhood

17. Football Team Owner

In 1983, Donald Trump purchased the New Jersey Generals, a United States Football League team. That year, Trump managed to lure Heisman Trophy winner Herschel Walker to the USFL. Then in 1985, Trump landed Boston College quarterback Doug Flutie. However, the USFL would fold before the 1986 season after losing an anti-trust case against the more established National Football League, as well as Trump’s strategy of moving the league from its spring/summer schedule to compete directly with the NFL in fall/winter.