How Trump’s NFL Obsession Led to His Fraud Conviction — and Presidency

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It was the spring of 2014, and Chuck Sonntag just had his left leg amputated. The rare bone disease he’d been struggling with all of his life forced him to get the surgery, just like it had taken his left arm. Now he was in a rehab center, trying to recover, when he got a call from an old friend, the political operative Michael Caputo. 

Growing up, Caputo, Sonntag, and a few more buddies had a crew they called the Big Tree Boys, a reference to their neighborhood of Orchard Park, New York, right next to the Buffalo Bills’ stadium. They worked out a scam where Sonntag would use his disability to help the other Boys sneak into games. “I was in a wheelchair, and I would go around the gate and see what security guy would let me in for five bucks,” Sonntag tells me. “And then when he opened up the gate, all my brothers and my friends [would] jump on the other side.” The break-ins continued, even during the off-season. Sometimes they’d let themselves in to see the Grateful Dead. At others, they’d do a bit of shopping. “They had a lot of equipment over there. And so the first thing we hoisted was some bolt cutters,” Sonntag says. “And then we emptied out their tool supply, you know, the nice electric drills. We filled up the garage and sold them. So yeah, we did pretty good.”

Caputo had already come by the rehab facility once to check on his friend and reminisce about old capers. But on this day, Caputo wasn’t calling with more well wishes. He was on a mission for his client, Donald J. Trump. It seemed Trump wanted to buy the Boys’ beloved Bills.   Even more than that, he wanted to block one of his main rivals for the Bills from becoming their new owner, and possibly moving the team to Canada. That rival: the superstar hair-rocker Jon Bon Jovi.

It was a battle Trump needed some local muscle to help fight, so he enlisted Caputo, who knew just the superfan to call. 

“Mike comes to me,” Sonntag recalls, “he said, ‘Listen, you got to do something. Trump’s gonna buy the Buffalo Bills. And he wants to know if the Bills fans still want them here.’ And I told Mike, I said, ‘Mike, I just got my leg cut off two days ago. What do you want me to do?’”  

What happened next in the spring of 2014 was weird and silly and short-lived. But it provided something of a preview of the decade to come, and how Trump would operate in it: the petty obsessions, the celebrity fights, the flex-in-the-endzone machismo, the run-ins with the law. When Trump tried to acquire the Bills, he inflated his net worth by billions of dollars, part of his ham-handed effort to prove to the NFL that he was rich enough to join the owners’ club. That was one of many, many times he attempted to land a deal by overstating his financial wherewithal, and it was one of the many, many examples the New York attorney general’s office used to prove earlier this year that the Trump Organization had repeatedly, serially engaged in fraud. Trump’s lawyers are appealing, but he’s right now on the hook for $450 million — that’s in addition to the roughly $90 million he owes E. Jean Carroll, and all the other court cases still in front of him, especially if he loses November’s election. 

Had Trump’s play for the Bills actually worked out, he might never have been in this position. In fact, he might not have run for president in the first place.

“If he was doing that [owning and operating the Bills] and running that kind of a business, that would have been relatively new for him,” one former Trump associate tells me. “I think it would have been hard for him to then put all his energy into running for president.” 

Trump himself said as much in February of 2016, right after a debate with Ted Cruz and Marco Rubio and Jeb Bush and all the rest, amid the campaign that’s upended our politics ever since: “If I bought that team, I wouldn’t be doing what I’m doing.” 

THESE DAYS, TRUMP is more associated with sports like MMA and pro wrestling. But he’s been infatuated with football, at the idea of owning a football team, for far longer — more than 40 years. 

It’s easy to see the appeal, if you get inside Trump’s head: the glamor, the violence, the cheerleaders, the publicity, the power. Becoming an NFL owner meant “joining one of the most exclusive clubs,” the Trump associate says. “It’s like being a U.S. senator, being an NFL owner. There’s a very small number of people in those clubs. And obviously as a business, it couldn’t be more lucrative, right?”

Trump showed in his early football dealings the same relationship to the truth that would become a hallmark of his political career, and the same kind of business acumen that led to his six bankruptcies. In 1981, Trump was part of a group that tried to acquire the Baltimore Colts; when the offer was rebuffed, he denied ever making it. Not long afterward, he passed on buying the Dallas Cowboys for $50 million. “In my opinion, only a loser can buy the Dallas Cowboys,” he said. (Today, the Cowboys are worth over $10 billion, perhaps because they had owners other than Donald Trump.) Instead, Trump paid an estimated $9 million for the New Jersey Generals, a club in the United States Football League, a fledgling alternative to the NFL, in 1983. Afterward, Trump quickly announced that he was on the verge of luring legendary Miami Dolphins coach Don Shula to the new, B-league team. “One of the little obstacles is he’d like an apartment in a building I have on Fifth Avenue called Trump Tower,” Trump claimed to sportscaster Brent Musburger. The next day, Shula said he was “not interested in the United States Football League and the New Jersey Generals in particular.” 

Trump did manage to recruit former NFL Most Valuable Player Brian Sipe to play alongside Generals running back (and future MAGA candidate for U.S. Senate) Herschel Walker. Trump also tried to woo New York Giants star Lawrence Taylor, promising to keep the negotiations and a $1 million signing bonus secret. According to the USFL history Football for a Buck, Trump “immediately” called “the various New York newspapers,” pretending to be his publicist, “John Barron.” Taylor never played for Trump (though he later backed him as a political candidate).

Meanwhile, Trump was engineering a far bigger — and far more damaging — con. The USFL had early success by playing in the spring, when the NFL season was done and football fans were starved for action. Trump pushed the USFL owners to move to the fall and have their new league take on the powerhouse of pro sports head to head. Trump was clear in his intentions; he wanted the leagues to merge so he could get a big-boy franchise out of it. (“I have the money to get into the NFL,” he told his fellow owners, “and that’s where I plan on being.”) This was the business equivalent of the Charge of the Light Brigade, of Jonestown, of Sid and Nancy at the Chelsea Hotel. Somehow, Trump managed to convince those owners to go along. 

It was an instant disaster. The TV networks already had their Sundays filled. The stadiums were already booked for fall football, so the league champion USFL Philadelphia Stars had to play in College Park, Maryland, 127 miles away. In response, Trump and his lawyer Roy Cohn deployed a favorite tactic: They took the National Football League to court, filing an antitrust suit. “Is this action akin to a drowning man grabbing at razor-sharp knives to stay afloat?” a CNN reporter wondered at the time. Well, yes, even though the USFL actually wound up winning. The NFL teams really did collude to keep out competition (they literally had a playbook for doing so, written by a famed Harvard Business School professor, you can read it right here). But the jury also thought the USFL’s Trump-led strategy to play in the fall and directly challenge the National Football League was so insane, they awarded the USFL a whopping one dollar in damages. The USFL had hoped to win as much as $1.69 billion through the suit; they were counting on it, because the shift to the fall had so severely damaged their economic viability. Without that money, the league closed shop. Trump’s scheme to win an NFL team on the cheap had crushed not only his own dream but 13 other franchises.

Trump looked at buying the New England Patriots a few years later in 1988, “but his people told him between the team and the stadium there was $104 million in debt, and that was too much for him to handle,” a source told The Boston Globe at the time. (Trump allegedly had a net worth of $1 billion by then.) Over the years that followed, Trump became close with many an NFL owner, especially the packaging-and-paper magnate Bob Kraft, who eventually bought the Patriots. Kraft’s star player Tom Brady was an even more intense object of fascination. Both in private and in public, Trump would float the idea of the comically-handsome quarterback dating Ivanka Trump. (“Tom Brady would make any father-in-law proud,” he told Playboy.) This kind of talk continued long after Ivanka linked up with Jared Kushner — so much so, it became a running joke in Trump Tower, according to former aide Sam Nunberg: “If Brady came up [in conversation] and Ivanka was in the office, she would talk about, ‘I told you he wouldn’t be a good husband’ or ‘I told you he wouldn’t be loyal.’”  

But Trump’s thirst for an NFL connection couldn’t be slaked through chit chat and a little light innuendo. So when the Bills’ longtime owner died on March 25, 2014 — the same week Chuck Sonntag had his leg amputated — Trump made his move.

TRUMP FACED TWO hurdles. One was convincing NFL executives that he actually had the money to buy the team. Here, he employed another favorite tactic, the same one he had used to get a nine-figure loan on the Trump International Hotel & Tower in Chicago — which according to court documents he’d told tax authorities was worthless — and to obtain the lease for what became the Trump Hotel in Washington, D.C.: A judge found that he inflated the value of his holdings and got a major financial institution to sign off on the higher number. Trump’s underlings drew up documents in the early summer of 2014 stating that Trump was worth $5.1 billion and had $310 million in cash on hand. Deutsche Bank certified the figures, without taking “any independent procedures to verify the accuracy” of them, a prosecutor later noted.

“Our understanding is that Mr. Donald J. Trump has made, or intends to make, a bid for the Buffalo Bills in the amount of $1 billion in the aggregate,” a Deutsche Bank managing director wrote. “It is our assessment that Mr. Donald J. Trump would have the financial wherewithal to fund his bid.” 

Trump upped the ante in a follow-up note to the Bills’ bankers at Morgan Stanley: “I have a net worth in excess of Eight Billion Dollars (financial statements to be provided upon request), comprised of substantial cash balances, highly liquid assets (including Class A real estate) and very little debt.” That August, Trump met with the Morgan Stanley executives in Detroit. The statements were not, in fact, provided upon request, as one of the bankers recounted at the civil fraud trial that this past February resulted in a $450 million judgment against the Trump Organization. 

“Do you recall whether Mr. Trump provided any documents to you at the presentation?” a prosecutor asked.

The banker answered, “He gave us handouts of the Forbes list of the top-paid entertainers.”

Trump’s second big obstacle was that another group of bidders had a major head start on the negotiations — and a famous face. Jon Bon Jovi had linked up with the owners of the Toronto Maple Leafs and Toronto Blue Jays to make a run at the Bills, too. Unlike their Manhattan-based rival, the Canada-Jersey crew seemed to have the balance sheet for a credible bid. Fans were worried about any new owners relocating the team, though, and the Bills had already played a number of games north of the border. That gave Trump an opening, and he knew who to call to crack it wide.  

A FEW DAYS after Chuck Sonntag’s leg operation, he got the call from Caputo, who had just heard from Trump. “He was going to make Michael Caputo the general manager of the Bills,” Sonntag recalls. (Caputo, for his part, tells me that’s just a Big Tree rumor. Otherwise, he wouldn’t comment for this story.) The operative showed up to Sonntag’s rehab days later with a couple of old members of the Big Tree Boys: a cop named Charles Pellien and a T-shirt maker named Paul Rudolph, who brought his buddy Anthony Lynch. All of them were civic-minded Buffalonians, raising money for local charities. (Pellien secured Kid Rock’s help for one benefit, and Lynch told me a story about a charity event that somehow involved a TV matchmaker and getting stuffed into an Elmo suit.) All of them were Bills fanatics. And all of them loved a good dust-up. “I mean literally, Big Tree Boys were a street gang. We would get in fights with other gangs in the street. It was like West Side Story without tunes,” one Boy tells me. 

They decided to start a group, 12th Man Thunder, which would push for the team to stay in their home city — and, more importantly, would publicly pound Bon Jovi and his associates for allegedly trying to take the Bills away. “Trump knew he couldn’t outbid the Canadians,” Caputo told GQ in 2017. But, with a little help, he could make them completely unpalatable to Buffalo. 

So the Big Tree Boys and 12th Man Thunder did. “We went to every restaurant and bar and told them they couldn’t play Bon Jovi,” Sonntag recalls. It worked. One radio station, then another, agreed to take the band out of their rotation. Jack FM 92.9 even re-recorded “Living on a Prayer” with new anti-Jovi lyrics. Businesses all over town hung up signs declaring Buffalo a “Bon Jovi Free Zone.” Pellian claimed local cover band playing Bon Jovi at a bar were booed and pelted with anti-Bon Jovi posters.

Jon Bon Jovi wrote an open letter to the city, assuring fans he’d never move the Bills. The Big Tree Boys weren’t having it. “This is just like a politician saying what he needs to say to get elected,” Pellien told reporters, somewhat ironically in retrospect. “He’s saying what he needs to say to get his hands on our team.”

Trump had to distance himself from the whole thing, because NFL rules said he couldn’t be part of any PR efforts surrounding the sale. But he seemed to keep tabs on the campaign. Once, Sonntag says, Caputo was driving him to a radio interview to promote their efforts when Trump called. “[Caputo] said, ‘I’m taking my friend to AM Buffalo about banning Bon Jovi,’” Sonntag recalls. “And Trump said, ‘Hey, how’s your friend doing?’ …That was pretty cool.”

In the end, neither Bon Jovi nor Trump got the Bills. The Pegula family, who own the Buffalo Sabres hockey franchise, purchased the team. What would’ve happened if Trump had somehow won this fight in 2014? Would he still have run for president the next year? Nunberg, the former aide, says yes. “The reality TV boardroom helped propel him to the presidency. Can you imagine [the effect of] being an NFL owner?” he asks.

Many others disagree. “Donald Trump called yours truly, that would be me. And he said that he wanted to purchase the Buffalo Bills,” ESPN’s Stephen A. Smith told his audience eight years later. “And I’ll never forget what he said to me. He said, ‘If they screw me over, I’m gonna show them. I’m gonna get them all back. I’m going to run for President of the United States.’ That’s what he said to me back in 2014.”

THE AFFAIR HAD all kinds of after-effects. Jon Bon Jovi said it “took years of therapy” to deal with the boycott campaign. He wouldn’t comment for this story, but he made it clear to GQ that he’s still not fully over what happened: “I won’t ever go back to the city of Buffalo. You will never see my face in Buffalo ever. I have knocked it off the map.” 

Texas A&M threatened to sue Sonntag and Caputo and friends for violating the school’s “12th Man” copyright. Trump hired a lawyer for the Big Tree crew, Sonntag remembers, while Caputo launched a PR counteroffensive and quickly turned the tables on A&M, portraying them as bullies picking on the double amputee. (Keith Olbermann declared the university president the “Worst Person in the Sports World.”) 

“A week goes by. The lawyer calls me, and he says, ‘Hey, Chuck, what do you want?’” Sonntag says. “I said, ‘What do you mean?’ They were suing me. ‘They want to pay you. Just call off the dogs.’ And so I said, quickly, ‘How about twenty-five grand?’” The group renamed itself Bills Fan Thunder, and uses the money to this day to buy underprivileged kids tickets to home games. Sonntag and the old Big Tree Boys still go to Dead & Company shows together. 

Pellien continues to help run the fan group, but his opponents have moved well beyond hair rockers. He participated in anti-lockdown protests during the pandemic, and started a “patriot” organization that some outside observers have likened to a far-right militia — a charge the group denies. At least one of the group’s demonstrations devolved into a brawl with antifascist counter-protesters. “My flashlight was dented,” Pellien wrote on Facebook, according to The Washington Post. “Not sure if it was from head #1 or head #2.” (Pellien wouldn’t comment for this story.)

Caputo worked on Trump’s first presidential campaign for a while. In 2017, he was swept up in the various Russia investigations; he had previously been a PR man for Moscow’s state-run energy company Gazprom. In April 2020, he was appointed to be an assistant secretary for public affairs at the Department of Health and Human Services. Emails showed him trying to browbeat Centers for Disease Control scientists whom he accused of exaggerating the lethality of Covid-19. He apologized to department staffers for a deeply unhinged Facebook video, and resigned from the department after receiving a cancer diagnosis. Today, he’s a policy adviser on Trump’s 2024 campaign. 

About that. We all know what happened to Trump in the ensuing years. But it can be easy to forget the strangely central role that professional football has played in his political life. “What used to be considered a great tackle, a violent head-on… now they tackle. ‘Oh, head-on-head collision, 15 yards,’” he complained at a January 2016 rally. “Football has become soft like our country has become soft.” A few months later, then-Buffalo Bills head coach Rex Ryan introduced the candidate at a rally in western New York, where Trump praised the team’s new owners before jeering at a protester, “Go home to mommy.” NFL owners and their businesses wound up contributing $7.7 million to Trump’s inaugural. 

That didn’t stop him from repeatedly going after the league when more and more players began taking a knee during the national anthem. “I have so many friends that are owners. They’re in a box,” he told Fox News. “I think they’re afraid of their players, you want to know the truth, and I think it’s disgraceful.” In a subsequent interview, he said of player-protesters, “Shouldn’t be playing, shouldn’t be there. Maybe you shouldn’t be in the country.” 

The controversy — and Trump’s attitude toward football — came up again in a 2019 interview with CBS. He was asked whether he’d let his son Barron play the game. “I would have a hard time with it,” Trump answered. “I mean, it’s a dangerous sport.”