Key Takeaways
- Charles Oakley’s lawsuit against Madison Square Garden and Knicks owner James Dolan was dismissed for a third time, but he vowed to keep fighting, posting “#ItsNotOver” and “#JuryTrial” on Instagram as his lawyer plans another appeal.
- Judge Richard J. Sullivan ruled that no rational jury could find Oakley reasonably feared wrongful physical contact and cited video and witness accounts showing he could have left but instead got physical with security during the 2017 incident.
- MSG declared Oakley’s claims dismissed “in their entirety,” said it will pursue legal action against his attorney for “frivolous litigation,” and the long-running case—which has been dismissed and revived multiple times—has already led to Oakley being ordered to pay about $642,000 in MSG’s legal fees.
Charles Oakley isn't ready to call his legal battle with Madison Square Garden finished, even after a federal judge dismissed his lawsuit for the third time. One day after the latest ruling, the former New York Knicks star posted an old photo from his playing career on Instagram with two hashtags that made his intentions clear: “#ItsNotOver” and “#JuryTrial.”
According to The New York Post, Oakley's response came after U.S. Circuit Judge Richard J. Sullivan dismissed the remaining claims against MSG and its related entities on Friday. The decision represents the latest turn in a case that has repeatedly been dismissed and revived since Oakley sued over his controversial removal from Madison Square Garden in 2017. His attorney, Douglas Wigdor, has already indicated that the legal team intends to pursue another appeal.
“We are disappointed with the Court's rulings,” Wigdor said in a statement. “We believe there are conflicting accounts and only a jury can decide what exactly happened.”
He added that Oakley's team hopes the Second Circuit will once again reverse the dismissal and send the dispute to a jury trial.
Sullivan reached a different conclusion. In his ruling, the judge wrote that “no rational jury could conclude that Oakley reasonably feared himself at risk of wrongful physical contact” during the encounter.
He also cited video footage and witness testimony that he said showed Oakley had an opportunity to leave the arena but instead became physical with security.
MSG responded by declaring Oakley's claims dismissed “in their entirety” and announcing plans to pursue legal action against Wigdor and his firm. The company accused Oakley's attorneys of pursuing false claims and engaging in “frivolous litigation” over the past nine years.
The dispute began when Oakley attended a Knicks game against the Los Angeles Clippers on February 8, 2017. Security approached the longtime Knicks fan favorite, and the encounter quickly escalated before Oakley was removed from the arena in handcuffs.
He was arrested on assault and criminal trespassing charges, which were later dropped. Oakley subsequently sued MSG and Dolan, with his claims including assault, battery, false imprisonment, and defamation.
The case has taken an unusually winding path since then. A federal court dismissed Oakley's lawsuit in 2020 before an appeals court revived his assault and battery claims later that year. It was dismissed again in 2021, only for the Second Circuit to revive it in 2023, finding that the question of whether security used reasonable force was generally one for a jury.
Oakley has faced other setbacks during the litigation. In 2025, a judge ordered him to pay approximately $642,000 in attorney fees and costs connected to MSG's efforts to recover deleted text messages.
