American football fans never thought they would see the day - the head of the National Football League standing shoulder to shoulder with Donald Trump in the Oval Office.

Trump has frequently traded blows with the NFL since he first became US president in 2017, but he and America's most popular sports league have been sparring partners for more than 40 years.

Trump's 'feud' with the NFL has involved him testifying against the league and failing, on multiple occasions, to buy a team. It may even have propelled him to the presidency.

When NFL commissioner Roger Goodell joined Trump in May to announce the NFL Draft would be coming to Washington, D.C. for the first time, it seemed Trump had finally made friends with arguably his oldest foe.

With this season set to conclude with Super Bowl 60 on Sunday, let's examine Trump's long and complicated relationship with the NFL and why it could be set for another twist.

Lawsuit fails to force league merger

Already a real-estate magnate at that point, Trump viewed owning an American football team as a means of building his brand. After attempting to acquire an NFL franchise, Trump bought the New Jersey Generals in September 1983.

The Generals were founding members of the USFL, which started in the spring of 1983 so did not clash with the NFL. The new league managed to lure top players from the NFL and the college game.

The Generals improved during their two seasons under Trump but lost in the first round of the play-offs in both 1984 and 1985. However, Trump had made his intentions clear from the outset—he wanted to go directly against the NFL in the autumn-winter.

In August 1984, Trump convinced team owners to vote on switching to an autumn-winter schedule from 1986. Then, two months later, the USFL filed an anti-trust lawsuit against the NFL, led by Trump.

The trial lasted 42 days, and although a jury found the NFL to be an 'illegal monopoly', it rejected the other charges, awarding the USFL just $3. Days after the verdict, the league folded.

Trump's subsequent relationship with the NFL was rocky at best. He attempted to buy the Buffalo Bills in 2014 but was ultimately outbid, which he claimed was a significant unfairness that contributed to his decision to run for president.

Trump’s criticisms of player protests during the national anthem have also defined his interactions with the NFL. As tensions flared, it became increasingly clear that Trump's interest in the NFL wasn't solely about sports.

Whether he will rekindle that interest remains to be seen, especially as he pushes against them once again with the upcoming Super Bowl event threatening his political gains. Trump continues to navigate the complex and intertwining worlds of sports and politics.