Ever wonder how close we came to a world where the 45th President was just another guy in an owner's box on Sundays? It’s one of those wild "butterfly effect" moments in American history. In 2014, the sports world and the political world almost collided in Western New York. Donald Trump and the Buffalo Bills were a headline that nearly changed everything.
Honestly, it wasn’t just a passing fancy or a publicity stunt for a reality show. Trump was actually a finalist to buy the team. After the legendary Ralph Wilson passed away at 95, the franchise was up for grabs, and the bidding war got intense. Trump was right in the middle of it, facing off against rock star Jon Bon Jovi and the eventually victorious Terry Pegula.
The $1 Billion Poker Game
Trump didn't just kick the tires. He put a $1 billion all-cash offer on the table. He even sent a letter of credit to Morgan Stanley to show he wasn't playing around. At the time, the Bills were valued somewhere around $870 million, so a billion seemed like a safe bet. He told The Buffalo News back then that he’d keep the team in Buffalo because his plane could get there from NYC in an hour. Basically, he didn't want a five-hour flight to some other city.
But there’s a catch. Trump didn't want to overpay. He called the final price "ridiculous."
While he was bidding $1 billion, Terry Pegula—who already owned the Buffalo Sabres—swooped in with a massive $1.4 billion bid. That’s a $400 million gap. In the world of NFL ownership, that’s not a gap; it’s a canyon. Trump later tweeted that he was glad he didn't get them because the NFL had become "boring" and "too soft," but the reality was simpler: he got outspent.
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Why the NFL Bankers Were Skeptical
It wasn't just about the cash. Documents that surfaced during Trump’s later civil fraud trials showed that the investment bankers at Morgan Stanley were pretty skeptical of his chances from the jump. K. Don Cornwell, an executive at the bank, wrote in internal emails that Trump had "little chance" of being approved by the NFL.
Why? The league has a long memory.
- The USFL Grudge: Back in the 80s, Trump owned the New Jersey Generals in the rival USFL. He led a massive antitrust lawsuit against the NFL. He technically won, but the jury only awarded the USFL $3. That lawsuit basically killed the USFL, and the NFL owners weren't exactly lining up to invite the guy who tried to sue them into their exclusive club.
- The Casino Factor: At the time, the NFL had incredibly strict rules about owners being involved in gambling. Trump’s Atlantic City holdings were a massive red flag for the league’s buttoned-up culture.
- Financial Transparency: Michael Cohen, Trump's former lawyer, testified later that Trump didn't want to release his full financial statements until he was named the "final bidder." The NFL is notoriously invasive about finances. They want to see every penny and every debt.
The Ultimate "What If"
This is where it gets crazy. Trump himself has said that if his bid for the Donald Trump Buffalo Bills deal had gone through, he probably wouldn't have run for President in 2016. In a 2016 interview with the Associated Press, he admitted, "If I bought that team, I wouldn't be doing what I'm doing."
Imagine that.
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Instead of rallies, he’d be worrying about salary caps and draft picks. Instead of the Oval Office, he’d be sitting in a suite at Highmark Stadium. Bills fans—who are famously intense (looking at you, Bills Mafia)—would have been his primary constituents.
What Most People Get Wrong About the Bid
A lot of people think Trump was just trying to get his name in the papers. While he definitely loves the spotlight, those who were in the room, including Russ Brandon (the Bills' CEO at the time), confirmed he had multiple serious conversations about the purchase. He was obsessed with the idea of being an NFL owner. He’d tried to buy the Colts in the 80s and kicked the tires on the New England Patriots too.
Some critics argue his bid was a "paper tiger" backed by inflated asset values. During the New York fraud trial, prosecutors alleged he used "deceptive" financial statements to back his bid. Trump, of course, denied this, claiming his brand value actually made him worth more than what was on paper.
The Aftermath for Buffalo
Looking back, Buffalo fans mostly feel they dodged a bullet or hit the jackpot, depending on who you ask. Terry Pegula bought the team, kept them in Buffalo, and eventually drafted Josh Allen. Trump, meanwhile, took a very different path.
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After losing the bid, Trump took a few shots at the team on Twitter. He predicted they’d never be winners under Pegula. That tweet famously resurfaced when the Bills won the AFC East in 2020. Fans didn't forget.
Actionable Insights: Lessons from the Bid
If you're looking at this from a business or history perspective, there are a few real takeaways:
- Valuation is subjective, but cash is king: Trump’s $1 billion was a fair market offer, but Pegula’s $1.4 billion was an "emotional" offer to ensure he won. In high-stakes acquisitions, the "fair" price rarely wins.
- Relationship capital matters: You can’t sue an organization (like the NFL) and expect them to welcome you into the boardroom twenty years later without some serious friction.
- Check the rules first: The NFL’s ownership requirements (30% equity, strict debt limits, no gambling ties) were always going to be a massive hurdle for Trump’s business model, which relied heavily on branding and real estate leverage.
The story of Donald Trump and the Buffalo Bills remains a fascinating footnote. It’s the moment where sports history and political history almost became the same thing.
Next Steps for You:
- Review the NFL's current ownership rules: If you're interested in the business side, look at how the league recently relaxed rules to allow private equity firms to buy minority stakes—a huge shift from the 2014 era.
- Explore the "USFL vs. NFL" documentary: For the full backstory on why the NFL owners were so wary of Trump, check out the 30 for 30 film "Small Potatoes: Who Killed the USFL?"
- Compare the 2014 sale to recent ones: Look at the sale of the Washington Commanders for $6.05 billion to see how much team values have exploded since Trump’s $1 billion bid.