Charles Oakley's lawsuit against Madison Square Garden and owner James Dolan has been dismissed for the third time, marking another development in a legal dispute that began in 2017. The dismissal came on Friday.
MSG issued a statement asserting that the court had dismissed all claims in their entirety and announced plans to pursue legal action against Oakley's attorney, Douglas Wigdor, and his firm, accusing them of "years of frivolous litigation and their blatant abuse of the judicial system."
Wigdor expressed disappointment with the ruling but maintained hope for a jury trial, stating that "conflicting accounts" exist and "only a jury can decide what exactly happened." He indicated an appeal to the Second Circuit was possible.
The legal drama dates back to February 2017, when Oakley was ejected from Madison Square Garden during an altercation with security guards. Although the initial charges were dropped, Oakley filed a lawsuit later that year alleging assault, false imprisonment, and defamation. That lawsuit was dismissed in February 2020.
However, the case saw reversals. The 2nd Circuit Court of Appeals revived the dismissal of battery and assault claims in November 2020. In May 2023, the appeals court again ruled that the "question of whether the use of force was reasonable under the circumstances is generally best left for a jury to decide," reviving the case for a second time.
Despite these reversals, a third dismissal followed. In the recent opinion and order, Circuit Judge Richard J. Sullivan 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." Sullivan noted that "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's written assessment stated that "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."
Oakley, a prominent player for the Knicks for a decade and a key figure in their 1990s success, had a public falling out with Dolan that has been a lingering issue for the franchise. Reports in 2025 suggested the team was open to welcoming Oakley back as a "celebrated team alumnus" if he dropped the lawsuit. An initial ban instituted by Dolan in 2017 had previously been lifted, and Oakley attended playoff games on the road during the Knicks' championship run in the spring.