“What if Donald Trump purchased the Buffalo Bills?” remains one of the most interesting alternate-history scenarios because it would have changed both American sports and politics.
Without Trump, the Bills are thriving. They have arguably the best quarterback in the sport and just opened a brand-new, state-of-the-art facility in Orchard Park, New York.
With Trump, America is, well, take a look around and be your own judge.
As the Bills opened their new stadium against the Detroit Lions on Thursday Night Football, Al Michaels offered a brief history lesson as to how Terry Pegula ended up purchasing the team in 2014.
“The other bidder? Donald J. Trump, who said publicly, ‘I’m gonna write a cashier’s check for a billion dollars.’ League said, ‘We’ll take Pegula.'” – Al Michaels on the Buffalo Bills sale in 2014 pic.twitter.com/25HBhFWfVH
— Awful Announcing (@awfulannouncing) September 18, 2026
“Ralph Wilson founded this team in the American Football League in 1960. Ralph, a terrific man, died in 2014; the team was put up for sale. There were basically three bidders,” Michaels said. “Pegula who won it at $1.4 billion. A Toronto group, Jon Bon Jovi was in it…And the other bidder? Donald J. Trump, who said publicly, ‘I’m gonna write a cashier’s check for a billion dollars. League said, ‘Nah, we’ll take Pegula.’”
Michaels similarly took a subtle dig at Trump during the preseason, when he joked about the president’s attempt at renaming Lake Erie. And while Michaels didn’t say anything insulting about the president with his latest subtle quip, Trump never likes to see his losses displayed in front of a large audience.
Some question whether Trump had enough money to buy the Bills back in 2014. But even with enough money, Trump was always a long shot, given he was at odds with the NFL for decades after buying into the USFL and trying to force a merger. Trump later led an $1.5 billion antitrust lawsuit against the NFL, which he ultimately won, but earned just $3.76 in damages.
Decades later, Trump tried to buy into the NFL through the Bills. Stephen A. Smith has long claimed Trump called him during his bid for the Bills and threatened to get back at the NFL by running for president if they didn’t let him into their owners’ club. Trump seemingly tried to get back at the NFL early in his first term as president by politicizing Colin Kaepernick’s protest. Fast forward to 2026, and the NFL seems unharmed by Trump, still the most powerful entertainment entity in the United States.
Surely, the NFL looks back fondly at its decision to let Pegula purchase the Bills instead of Trump. But instead of being the NFL’s problem, Trump was left to be America’s problem.
About Brandon Contes
Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to bcontes@thecomeback.com