President Donald Trump’s criticism of NFL players and the league itself at a political rally Friday evening, which he followed up with a series of tweets Saturday, marked the latest entry in his long-running dalliance with the NFL, which, in some ways, is like a super-elite country club whose membership Trump has never been able to attain.

In 1983, when the going rate for an NFL team was about $80 million, Trump spent $6 million to buy the New Jersey Generals of the rival U.S. Football League, which played its seasons in the spring.

In interviews after the real estate magnate announced his acquisition at a news conference in the atrium of Trump Tower, Trump claimed he decided to buy into the rival league because he wanted a challenge.

“I could’ve bought an NFL team if I wanted to. … But I’d rather create something from scratch,” Trump said. “I feel sorry for the poor guy who is going to buy the Dallas Cowboys. It’s a no-win situation for him, because if he wins, well, so what, they’ve won through the years, and if he loses … he’ll be known to the world as a loser.”

As owner of the Generals, Trump went on a spending spree that drew the ire of NFL owners. He landed Herschel Walker, the Heisman Trophy-winning running back at the University of Georgia, with what was then the richest contract in the history of professional football: $5 million over three years. A year later, Trump signed another Heisman Trophy winner — quarterback Doug Flutie out of Boston College — to a five-year deal worth $7 million. He tried to sign star linebacker Lawrence Taylor away from the New York Giants, forcing the Giants to give Taylor a raise.

Trump tried to lure coach Don Shula away from the Miami Dolphins and then claimed the discussions ended because Shula asked for one thing Trump would not offer: a free apartment in Trump Tower.

“Money is one thing, gold is another,” Trump said.

Shula denied this and said he ended the negotiations because Trump kept publicizing them. Dolphins owner Joe Robbie derided Trump as “engaged more in ballyhoo … than in a serious effort to build a franchise completely by sound professional management.”

In 1986, Trump convinced his fellow USFL owners to launch what amounted to a hostile takeover attempt: They moved the league’s schedule to the fall to compete directly with the NFL, then sued the NFL, alleging antitrust violations. Trump predicted to his fellow USFL owners that the lawsuit would result in a massive judgment — hundreds of millions if not billions of dollars in damages from the NFL — that would force the NFL to offer to merge the leagues.

In the trial, NFL attorneys framed their case around Trump, arguing that the lawsuit was a charade orchestrated by Trump as a way to get into the NFL on the cheap. The argument worked.

“I thought he was extremely arrogant and I thought that he was obviously trying to play the game,” juror Patricia Sibilia recalled in a telephone interview last year. “He wanted an NFL franchise. … The USFL was a cheap way in.”

The jury ruled that the NFL had violated antitrust law but concluded that the USFL’s financial struggles were of its own making and awarded only $1 in damages. In antitrust cases, damages are tripled, so Trump’s legal assault on the NFL won a grand total of $3. The USFL folded.

“Only Donald Trump could somehow turn the behemoth of the NFL into an underdog,” said Michael Tollin, director of the ESPN documentary “Small Potatoes: Who Killed the USFL?”

Trump lost an estimated $22 million on the New Jersey Generals. The Dallas Cowboys team — which Trump said he considered buying in 1983 but did not because you could succeed only “laterally” in the NFL — was sold in 1989 to Jerry Jones for $140 million. According to Forbes, the team, still owned by Jones, is now worth an estimated $4.8 billion, making it the world’s most valuable sports franchise.

After the USFL folded, Trump’s name arose periodically in discussions about NFL ownership. In 1988, he made a bid for the New England Patriots but ultimately bowed out. In 2014, Trump said he offered $1 billion for the Buffalo Bills, but he was bested by a $1.4 billion offer.

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“I did it a little tentatively,” Trump told the AP of his attempt to purchase the Bills. “When I put the bid in for the Buffalo Bills, I always was a little concerned if the NFL would remember how I knocked the hell out of them.”

For once, however, Trump expressed contentment with defeat.

”This is more exciting,” he said of running for president. ”And it’s a lot cheaper.”