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 that the NFL Draft would be coming to Washington DC for the first time, it seemed Trump had finally made friends with arguably his oldest foe.

Well, maybe not. With the current season set to conclude with Super Bowl 60 on Sunday, we examine Trump's long and complicated relationship with the NFL and why it could be set for another twist.

NFL commissioner Roger Goodell in the Oval Office with Donald Trump as the US president announces that Washington DC will host the NFL Draft in 2027

Already a real-estate magnate by 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 didn't want the USFL to remain a spring league; he wanted to go directly against the NFL in autumn-winter.

In August 1984, Trump convinced team owners to vote on switching to an autumn-winter schedule from 1986. Then, the USFL filed an anti-trust lawsuit against the NFL - led by Trump. The case went to trial in May 1986, asserting NFL’s monopoly on TV contracts.

Despite a jury finding the NFL was an 'illegal monopoly', they awarded just $3 to the USFL due to their debt concerns. The league folded soon after.

Fast forward to present day, Trump’s relationship with the NFL is more complex, affected by political maneuvers and public relations challenges, especially surrounding the controversy of national anthem protests initiated by quarterback Colin Kaepernick.

As Trump continues to influence the narrative of sports through political means, his interactions with the NFL promise further intrigue in the future. With developments like the anticipated 2027 draft in Washington DC, the dynamics between Trump and the league are as unpredictable as ever.