When the Knicks reached the 2026 Finals, their first since 1999, Madison Square Garden was filling with former Knicks. The team was back on the biggest stage in decades. Yet Adam Silver was asked about the one Knicks legend who wasn’t there: Charles Oakley.
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Silver then revealed that he and Michael Jordan had tried to broker peace between Oakley and James Dolan, but failed. He called it “a shame” and said the matter was still caught up in litigation. But Oakley did make it to Game 5 of the Finals in San Antonio. He was there when the Knicks won the championship, just not at home.
That long-running legal fight has now taken another turn. Judge Richard J. Sullivan has ruled in favor of Madison Square Garden, dismissing Oakley’s surviving assault and battery claims for the third time. The ruling is another setback for Oakley after the Second Circuit had twice revived those claims and sent the case back to federal court.
The latest ruling closes another chapter in a case that has been dismissed and revived multiple times since Oakley was removed from Madison Square Garden during a Knicks game in 2017. The case is not technically closed yet, as two motions remain pending, but Friday’s ruling is a major victory for MSG on the central claims that survived the earlier appeals.
Oakley had alleged assault, battery, false imprisonment and defamation stemming from the confrontation with arena security. His original complaint also named Dolan, but the claims against the Knicks owner were dismissed in 2020. The assault and battery claims that survived the appeals are now directed at MSG and related entities. MSG celebrated the ruling and turned its attention towards the former NBA star’s longtime attorney, Douglas Wigdor.
“For more than nine years, Mr. Oakley’s lawyers have pursued claims they knew were false,” MSG said in its statement. “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.”
U.S. District Judge Richard J. Sullivan, who is sitting by designation as a circuit judge, ruled that Oakley had not presented enough evidence for a reasonable jury to find that MSG security committed an actionable assault or that MSG intended to place Oakley in fear of unlawful physical contact.
“Even though the alleged assault occurred in the middle of Madison Square Garden in front of 19,000 and scores of cameras, Oakley concedes there’s no other witness — besides himself — who says he was pushed to the ground,” Sullivan wrote on the first page of his opinion and order.
The judge pointed to more than Oakley’s lack of supporting eyewitness testimony. He wrote that videos from multiple angles, sworn declarations and depositions showed Oakley had a reasonable opportunity to leave the Garden, that he instead engaged in physical violence and that he was never pushed to the ground as he alleged.
“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,” Sullivan wrote.
The legal dispute began on February 8, 2017, when Oakley was removed by security. He was sitting near Dolan during the Knicks’ game against the Los Angeles Clippers when the confrontation began. Oakley was handcuffed and arrested after the altercation, although the criminal charges were later dropped. Oakley filed a lawsuit later that year, alleging, among other claims, assault, battery, false imprisonment and defamation.
The case was initially dismissed in February 2020. But in November 2020, the appeals court reversed the dismissal of his assault and battery claims, allowing those portions of the case to continue.
The case was dismissed again in 2021. But in May 2023, the Second Circuit reversed that decision for a second time, holding that the question of whether the force used against Oakley was reasonable was generally a question best left for a jury. The case was sent back to Sullivan’s court, where the parties entered a lengthy discovery process.
That discovery process produced another unusual chapter in the fight. In 2024, Oakley’s lawyers discovered that text messages sent to and from his phone before February 2022 had been lost. Oakley had upgraded his phone without preserving the messages, leaving MSG to seek sanctions over the missing evidence.
In July 2025, Sullivan ruled that MSG could present evidence of the missing messages at a future trial and receive an adverse-inference instruction. Months later, another judge ordered Oakley to pay MSG $642,337.65 in attorneys’ fees and costs tied to the company’s efforts to recover the deleted messages. MSG had originally sought more than $1.5 million.
That history matters because Friday’s ruling did not arrive in isolation. By the time Sullivan considered the assault and battery claims again, the case had already produced multiple appeals, years of discovery and a six-figure fee award over lost evidence.
MSG is now seeking to take the fight beyond Oakley himself, saying it plans to pursue legal action against Wigdor over what it calls years of frivolous litigation. That remains MSG’s allegation; it is not a court finding that Wigdor or his firm engaged in misconduct.
And the dispute has remained personal for Oakley even as the legal case dragged on. In June, he said he had no plans to return to Madison Square Garden unless Dolan apologized. “He started it, he can make it go away,” Oakley said. “He’s the boss.”
Dolan has lifted the ban on Oakley, and he is allowed to attend games. The ban imposed after the 2017 incident was lifted later that year, meaning Oakley has technically been free to return to the Garden for years. He has chosen not to do so.
That distinction became especially striking during the Knicks’ 2026 championship run. Oakley attended road playoff games and was among the Knicks legends at Game 5 in San Antonio, where New York clinched the championship. But he remained absent when the series returned to the Garden.
For Knicks fans, that has created an odd split: Oakley is still visibly connected to the team and its history, but the building most closely associated with that history remains off limits in practice.
Previous reports indicated that Oak wanted a public apology, while The New York Post reported in 2025 that the Knicks were willing to welcome him back as a “celebrated team alumnus” if he dropped the lawsuit. Neither side has managed to turn that possibility into a reconciliation. That’s why multiple fans are pleading for it to end.
Fans hope for reconciliation between Dolan and Charles Oakley
“Hopefully, all parties will reconcile at some point in the near future,” one fan wrote. Another asked, “Can we broker a peace treaty now?”
Oakley has also made clear that his feelings toward the Knicks themselves are separate from his dispute with Dolan. During the Finals, he said he wanted the team to succeed despite his disagreement with its owner. “Even though me and the owner are in a dispute, I hope the team has success, especially for the city of New York,” Oakley said. “They’ve been waiting for it.”
While the judge dismissed it for the third time, Charles Oakley’s lawyer hasn’t given up.
“We are disappointed with the Court’s rulings,” Wigdor said in a statement to The New York Post. “We believe there are conflicting accounts, and only a jury can decide what exactly happened.”
Wigdor said he was hopeful the U.S. Court of Appeals for the Second Circuit would agree with Oakley’s position for a third time and send the case back for an immediate jury trial.
That would mean another appeal in a case that has already been revived twice. For now, however, Sullivan’s latest ruling leaves Oakley facing another defeat in the same courtroom where the dispute has spent years cycling between dismissal and revival.
And while the legal fight may continue, the larger Knicks question remains just as unresolved: Oakley has already been allowed back into the Garden, has watched his former team win a championship and has remained part of its wider story. The one thing that still hasn’t happened is the reunion fans keep asking for, Oakley and Dolan putting the 2017 fight behind them.