Imagine a world where Donald Trump wasn’t just building skyscrapers or residing in the Oval Office but owned one of the NFL’s most storied franchises, the New England Patriots. Back in 1988, this was nearly a reality.
Deep in negotiations, Trump had exclusive bargaining rights with the Sullivan family, who at the time were the owners of the Patriots. Their financial struggles were no secret, thanks in part to a failed $22 million investment in a Jacksons tour. For about two weeks, it seemed like Trump was on the verge of adding NFL owner to his resume, promising to keep the team in New England. But in the end, it was a deal that never crossed the finish line.
The sticking point? It wasn’t the mountain of debt the team was buried under, around $104 million from the team and stadium. Instead, the issue stemmed from a widespread reluctance among NFL owners to let Trump into their exclusive club.
The shadow of Trump’s history with the USFL loomed large. In 1983, Trump had purchased the New Jersey Generals and went all-in, signing big names like Doug Flutie in an audacious attempt to compete with the NFL. Unfortunately, this bold strategy didn’t end well, culminating in the USFL folding by 1985. The league’s subsequent antitrust lawsuit against the NFL did little to mend fences, despite technically winning a $3 settlement.
By the time Trump was attempting to buy the Patriots, he needed the green light from other NFL team owners. Yet, according to reports, the vote was far from in his favor. Many owners viewed him as an unpredictable force, someone “loathed” by his would-be peers in the inner circle. Even with preliminary negotiating rights, he never made a formal move since league approval was unlikely.
While not all owners were against him – Art Modell, the Browns’ then-owner, showed him some support – the winds were against Trump. Instead, Victor Kiam purchased the Patriots for $84 million, and the team’s ultimate fate would see Robert Kraft take the reins in 1994, leading to a dynasty era.
Trump didn’t abandon his NFL ambitions, however. Fast forward to 2014, and he was back in the fray trying to acquire the Buffalo Bills, only to be bested by the Pegula family. He even passed up the opportunity to purchase the Dallas Cowboys in the ’80s, dismissing it as a “sure money loser.”
Today’s NFL fans are left to muse over the what-ifs. What if the vote had swayed in Trump’s favor? Might we have seen him celebrating on the field with Tom Brady, hoisting those six Lombardi trophies? It’s a tantalizing scenario, a chapter of football history that almost was.
