Donald Trump passed on chance to buy the Patriots in 1988

According to the Boston Globe, Trump was approached by the Sullivan family about buying the team. Billy Sullivan founded the Patriots as members of the American Football League in 1960, but he was facing bankruptcy in 1988 and attempted to sell the team.

Although Trump was interested, he didn’t want the burden of taking on the team’s debts.

“Donald had a real interest and he felt the Sullivan family was honorable in their dealings with him,” a source close to Trump told The Boston Globe. “But his people told him between the team and the stadium there was $104 million in debt, and that was too much for him to handle.”

Instead Victor Kiam bought the team for $84 million and then was forced to sell the team four years later. Just a couple years after that, Robert Kraft bought the team for $172 million.

Two decades and four Lombardi Trophies later, the Patriots are now worth an estimated $2.6 billion, according to Forbes in August 2014, making them the second-most valuable NFL team.

Of course, purchasing the Patriots wasn’t as simple as Trump shaking hands with Sullivan. As Mike Florio of Pro Football Talk pointed out, Trump was at the forefront of an antitrust lawsuit filed against the NFL in 1986. As owner of the USFL’s New Jersey Generals, Trump pushed other USFL owners to challenge the NFL, although the lawsuit and the league proved unsuccessful ventures.

Convincing three-fourths of the NFL’s owners to then approve Trump, just two years after he filed suit against them, would have been an uphill climb. Then again, blazing through disapproval and jokes is something Trump has done before.