The bitter feud between Charles Oakley and James Dolan has dragged on since 2017. Oakley, a well-known player who played ten seasons in New York, sued the Knicks owner and Madison Square Garden after being ejected from a home game in handcuffs. Dolan, who was sitting only a couple of feet away, and the defendants argued in court that the former forward was drunk and belligerent.
Watch What’s Trending Now!
Although the case was dismissed in 2021, a federal appeals court overturned it in May 2023. However, last year, Oakley was ordered to pay $642,000 in attorney fees to Dolan’s representation after a judge scolded the NBA veteran for failing to preserve text messages following his arena ejection. About a year later, another piece of unfortunate news has hit Oakley.
“U.S. District Judge Richard J. Sullivan issued a 12-page ruling late Friday night, granting summary judgment in favor of MSG,” according to Front Office Sports.
Despite the latest dismissal, though, Oakley’s legal representatives insist they will fight on, planning yet another appeal to the U.S. Court of Appeals for the Second Circuit in search of a full jury trial.
“We are disappointed with the Court’s rulings,” Oakley’s attorneys said. “We believe there are conflicting accounts and only a jury can decide what exactly happened.”
In granting summary judgment, Judge Sullivan pointed out that extensive evidence, which included video footage from multiple camera angles, sworn witness declarations, and sworn depositions, contradicted Oakley‘s account of being physically assaulted by arena security officers. In fact, a video clip from the game showed Oakley getting physical and pushing security instead.
“Indeed, even though the alleged assault occurred in the middle of Madison Square Garden and in front of nineteen thousand fans and scores of video cameras, Oakley concedes that there is no other witness beside himself who says that he was pushed to the ground,” the judge wrote. “No rational jury could conclude that Oakley reasonably feared himself at risk of wrongful physical contact—let alone that MSG intended to stir such an apprehension.”
MSG has also issued a scathing statement celebrating the ruling while threatening to pursue counter-litigation, even though the case isn’t closed yet and two Oakley motions are still pending.
“For more than nine years, Mr. Oakley’s lawyers have pursued claims they knew were false,” MSG stated. “Those claims have now been dismissed by the court in their entirety—for the third time… We are pursuing legal action against Douglas Wigdor, and his unscrupulous law firm, to hold them accountable for years of frivolous litigation and their blatant abuse of the judicial system.”
The court’s latest dismissal reinforces a key legal milestone in the case in 2026 alone. Back in August, the case was in the U.S. District Court for the Southern District of New York, where Judge Sullivan formally overruled six specific objections raised by Oakley’s legal team. It upheld an earlier decision by U.S. Magistrate Judge Robyn F. Tarnofsky, which ordered Oakley to pay more than half a million in attorney fees and expenses to MSG Networks, Inc., Sphere Entertainment Group, LLC, and Madison Square Garden Sports Corp.
According to FOS, Oakley’s already paying it off and owes about $602,337.65. In evaluating the physical evidence surrounding the altercation near Knicks owner Dolan’s seat, Judge Sullivan stressed that the record leaves no room for Oakley’s claims of being victimized by security staff.
“Ample evidence – including videos from multiple angles and the unanimous testimony of every witness (even, to some extent, Oakley himself) – shows that Oakley had a reasonable opportunity to depart the Garden, that he instead resorted to physical violence, and that he was never pushed to the ground,” Sullivan wrote in court documents.
Oakley originally filed his civil lawsuit in September 2017, naming MSG and Dolan as defendants. While Dolan was dismissed as an individual defendant in 2020, Oakley’s primary assault claims against the corporate entities have swung between the federal district court and the appellate courts ever since.
Although Dolan briefly banned the fan favorite from the venue in 2017 before backing down later that year, Oakley has publicly refused to set foot inside Madison Square Garden until Dolan issues a formal personal apology.
New Yorkers also missed Oakley during the franchise’s first championship parade in June 2026. Several former players and franchise legends, like Walt Frazier and Patrick Ewing, joined Jalen Brunson and Co. Stephen A. Smith briefly spoke about Oakley, saying, “We love you. And not only that, those players love him.”
Oakley didn’t completely distance himself from the celebrations. He was spotted watching the parade with a group of people up in Harlem and declared that Knicks fans are the most passionate of the lot and had “earned” it.
In case you didn’t know, NBA Commissioner Adam Silver had revealed that he and Michael Jordan also tried to help Dolan and Oakley reach common ground and “broker peace,” but their efforts were “unsuccessful.”
Although two minor procedural motions filed by Oakley’s team technically remain pending on the docket, MSG’s summary judgment victory leaves the former NBA veteran facing both an uphill battle and a daunting $642,000 obligation.