Charles Oakley’s case against MSG gets dismissed for third time in latest twist to years-long legal drama

Charles Oakley’s lawsuit against Madison Square Garden and owner James Dolan was dismissed for a third time Friday, concluding another chapter to the legal battle involving the former Knicks star that dates back to when he was ejected from the Garden following an altercation with security guards in February 2017. 

MSG said in a statement that the claims were dismissed by the court “in their entirety” and that it planned to pursue legal action against Douglas Wigdor — Oakley’s lawyer — and “his unscrupulous law firm.” Wigdor, in a statement to The Post, expressed disappointment with the court’s ruling and still hoped for a jury trial. 

“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 a 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 case was initially tossed in early 2020, revived later that year, tossed again in 2021 and then revived for a second time in May 2023. 

“We are disappointed with the Court’s rulings,” Wigdor said in his statement to The Post. “We believe there are conflicting accounts and only a jury can decide what exactly happened. We are hopeful that the Second Circuit will agree for a third time and remand the case for an immediate jury trial.” 

Oakley, who spent 10 years as a player for the Knicks and was a key piece of the franchise’s success in the 1990s, was arrested and removed from the Garden during the Knicks game on Feb. 8, 2017, and while the charges were dropped, he filed a lawsuit later that year — alleging, in part, assault, false imprisonment and defamation. That lawsuit was dismissed in February 2020. The 2nd Circuit Court of Appeals reversed the dismissal of the battery and assault claims in November 2020. When the appeals court reversed it for a second time in 2023, it ruled that the “question of whether the use of force was reasonable under the circumstances is generally best left for a jury to decide.” 

But more than three years later, a third dismissal followed. In circuit judge Richard J. Sullivan’s opinion and order, he wrote that “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.” 

“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. 

Oakley’s public feud with Dolan has loomed over the Knicks since it began. The Post’s Jared Schwartz reported in 2025 that the team was willing to welcome Oakley back as a “celebrated team alumnus” if he dropped the lawsuit. An initial ban instituted by Dolan in 2017 had been lifted. Oakley attended playoff games on the road during the Knicks’ championship run in the spring. 

“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.