President Donald Trump's long-running feud with the NFL is entering a new phase, with the booming online sports gambling industry emerging as what The Hill describes as "a potential new frontier in a long-standing era of tensions between President Trump and the NFL."

Trump's grievances with the league stretch back decades, rooted in his four failed attempts to buy an NFL franchise. Those efforts span from the early 1980s, when he tried and failed to acquire the Baltimore Colts, to 2014, when he was outbid for the Buffalo Bills. Locked out of the league, Trump instead purchased the New Jersey Generals, a team in the ill-fated rival USFL.

In recent years, the friction has persisted on other fronts. Trump has clashed with the NFL over what The Hill characterizes as its occasional "social justice posture," which ran afoul of his MAGA agenda, and he has expressed distaste for the league's new kickoff rules, which were designed to protect players by reducing high-speed collisions. He has also privately suggested that the new stadium for the Washington Commanders should be named after him, even threatening to complicate the construction process otherwise.

Now, per The Hill's report, the fast-growing and increasingly lucrative world of online sports wagering is set to become the latest stage for the conflict.

"Part of the reason for the NFL's boom in the live sports marketplace is the legalization of online gambling and rising fan interest in fantasy sports," the report detailed. "The country's most followed professional league by wide margin, the NFL is navigating a sports media landscape increasingly driven by daily online wagering. The league's growth through gambling comes at a time when the federal government is facing intensifying questions about game integrity and the potential public health risks tied to habitual wagering, particularly among younger fans."

The report continued: "Prediction markets, which pose a competitive threat to the top online sportsbooks that do big business with the NFL, have received the backing of the Trump administration in court as they face state-level legal challenges and work to fend off regulation. It's all leading to a potential showdown between the NFL and [the] Trump administration in a heated debate over what constitutes sports gambling and how a booming industry essential to the league's bottom line should be regulated." For readers unfamiliar with the term, prediction markets are exchanges where users trade contracts tied to the outcomes of real-world events — sports included — placing them in direct competition with the sportsbooks that do big business with the league.

Atlantic journalist Mark Leibovich told The Hill that friction is almost inevitable given the history between Trump and the league's power brokers. "There's always a really good chance that any relationship between Trump and other powerful people is going to result in some friction, especially there's history of them keeping him out of the [NFL owners] club," Leibovich said. "And he knows he has leverage over them. It does seem like sports gambling is the clear and present existential threat to football. They've always been terrified of it, but now they're in bed with it."

Meanwhile, the Trump Justice Department has been weighing the possibility of a probe into the NFL's media rights dealmaking and the antitrust exemption rules that allow for the league's special arrangements. The Federal Communications Commission, for its part, is considering an investigation into how online sportsbooks market themselves — a move that, according to The Hill, "was seen by many sports and business observers as directly related to the government's potential scrutiny of the NFL's media rights strategy." The stakes are underscored by the reporting itself, which frames wagering as a booming industry essential to the league's bottom line — meaning any formal federal action would land directly on the financial machinery of the country's most followed professional league. From here, the markers to watch are whether the Justice Department moves ahead with a probe, whether the FCC proceeds with its review of sportsbook marketing, and how prediction markets fare in the state-level court challenges the administration has so far backed them against.