

In an alternate universe, Donald Trump might be best known not as a former president, but as the man who once owned the New England Patriots.
Back in 1988, Trump came surprisingly close to buying the franchise during a time of financial chaos for its then-owners, the Sullivan family.
Their gamble on a failed $22 million investment in a Jacksons concert tour had backfired, leaving the Patriots drowning in debt.
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With ownership scrambling for a lifeline, Trump stepped in and secured exclusive negotiating rights to purchase the team.
He even promised to keep the team rooted in New England-a reassurance for local fans and league executives alike.
But despite how serious the talks were, the deal never materialized. Not because of money, but because of something far more personal: the NFL didn’t want Trump.
The USFL, Bad Blood, and the League’s Rejection
To understand why Trump‘s Patriots deal fell apart, you have to look back a few years earlier-specifically to his involvement in the USFL.
In 1983, Trump bought the New Jersey Generals of the fledgling league and immediately made waves, throwing massive contracts at college stars like Doug Flutie and pushing for a fall schedule that directly competed with the NFL.
His ambition to force a merger or legal victory against the NFL led to the USFL‘s demise. The league technically won its antitrust case against the NFL in 1986, but the symbolic $3 awarded in damages underscored the failure.
Most NFL owners blamed Trump for the collapse, and by 1988, those wounds hadn’t healed.
So when Trump tried to enter their world again by purchasing the Patriots, the owners weren’t interested.
Reports from outlets like Boston.com revealed that many league executives simply “loathed” him.
Despite having two weeks of exclusive negotiating rights, Trump never submitted a formal offer-likely because he saw the writing on the wall. Without the required approval from existing owners, no purchase would ever go through.
Only a handful of voices supported Trump‘s NFL ambitions. Notably, former Browns owner Art Modell backed him.
But that wasn’t nearly enough. The Patriots were eventually sold to Victor Kiam for $84 million. Just six years later, Robert Kraft would take over and build a dynasty that won six Super Bowls.
This wasn’t Trump‘s only brush with NFL ownership. He tried again in 2014, attempting to buy the Buffalo Bills but lost out to Terry and Kim Pegula.
He also once passed on buying the Dallas Cowboys in the 1980s, dismissing them as a “sure money loser”-a statement that now reads like a historic miscalculation.
It’s hard not to wonder what could’ve been. What if Trump had owned the Patriots before Kraft? Could he have hired Bill Belichick? Drafted Tom Brady? Celebrated championships from the owner’s box? We’ll never know.
But in the long history of “almosts” in sports, Donald Trump owning the Patriots might be one of the wildest what-ifs the NFL has ever seen.
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