How Donald Trump was blocked from buying the Patriots—and what the NFL may have avoided

Long before he was president or a polarizing political figure, Donald Trump came close to becoming an NFL team owner. In 1988, he had his sights set on the New England Patriots, a franchise in financial chaos following a disastrous investment by its owners, the Sullivan family. Trump appeared poised to swoop in and save the day—but the NFL had other plans.In the late 1980s, the Patriots were a struggling franchise teetering on the edge. The Sullivan family, desperate after losing millions on a failed Jacksons concert tour investment, began looking for a buyer. Donald Trump quickly stepped up and secured exclusive negotiating rights. He even promised to keep the team in New England, which reassured fans and local leadership.Everything looked like it was lining up for Trump. He had the money. He had the access. But he didn’t have the support of the other NFL owners.To understand why the deal fell apart, you have to rewind to Trump's role in the downfall of the USFL, a short-lived league that tried to challenge the NFL. In 1983, Trump bought the New Jersey Generals and pushed the USFL to go head-to-head with the NFL by moving to a fall schedule. He also led the league into an antitrust lawsuit against the NFL.The USFL technically won—but was awarded just $3 in damages. The league collapsed shortly after, and most NFL owners blamed Trump. So when he came knocking again in 1988, they weren’t interested.According to Boston.com, many NFL executives “loathed” Trump. Despite having a two-week exclusive window, he never submitted a formal bid, likely realizing he wouldn’t get the required votes from existing owners. Only a few supported him, including former Browns owner Art Modell—but it wasn’t nearly enough.Trump walked away, and the Patriots were eventually sold to Victor Kiam for $84 million. Six years later, Robert Kraft bought the team and led them into the Tom Brady-Bill Belichick era that would define modern NFL dominance.Trump would try again in 2014, this time with the Buffalo Bills—but lost out to the Pegula family. He also passed on buying the Dallas Cowboys in the '80s, calling them a “sure money loser”—a comment that now reads like one of the worst misjudgments in sports business history.Also Read: “The death of my dream”: Gisele Bündchen’s tearful interview marked a turning point in her healing journey after Tom Brady divorceWhat if Trump had succeeded? Would Belichick and Brady still have joined the Patriots? The NFL dodged a bullet—or missed a massive what-if—depending on who you ask.