Judge Orders Charles Oakley to Pay $642K in MSG Legal-Fees Dispute

Former New York Knicks All-Star Charles Oakley has been ordered to pay more than $642,000 in attorney fees and costs to Madison Square Garden, a sanction tied to the loss of five years’ worth of text messages in his lawsuit over a 2017 ejection from a Knicks game.

The ruling was issued Friday, Oct. 31, by U.S. Magistrate Judge Robyn F. Tarnofsky in Manhattan federal court.

MSG’s lawyers at King & Spalding had asked for more than $1.5 million. Tarnofsky reduced that request, ultimately awarding about $604,000 in fees and trimming claimed costs to reach a total of roughly $642,337.

The fee award follows a blistering July order by U.S. Circuit Judge Richard Sullivan (sitting by designation in the Southern District of New York), who found Oakley failed to preserve messages from February 2017 to February 2022. Sullivan wrote that the loss of messages “cannot be credibly explained as involving anything other than bad faith.” He also held that MSG was prejudiced by the destruction.

Oakley, a 19-year NBA veteran who played for the Knicks from 1988 to 1998 and has a long-running feud with team owner James Dolan, sued after he was forcibly removed from his courtside seat on Feb. 8, 2017. His latest amended complaint, filed in April 2024, alleges assault and battery; MSG and affiliated entities deny wrongdoing. Reuters+1

In August 2024, Oakley’s legal team disclosed that the relevant texts were lost when he upgraded his phone after a prior device broke. The court noted Oakley had upgraded phones before without losing messages, a point that weighed into the sanctions analysis.

Following Tarnofsky’s Oct. 31 ruling, Oakley can pay the fee award or pursue an appeal. His attorney, Valdi Licul of Wigdor, said they “disagree that MSG is entitled to any recovery and will promptly seek to appeal.”

The order adds another turn to an eight-year legal fight marked by dueling sanctions motions and repeated skirmishes over litigation conduct. In earlier rounds, MSG pressed for sweeping fees while Oakley sought sanctions of his own, underscoring how the 2017 fracas has evolved into a broader, costly courtroom battle.

Bloomberg Law and Law360 also reported the award figure and date, aligning with Reuters’ account.

Key numbers: MSG requested >$1.5M; awarded ≈$642,337 (≈$604,000 in fees + ≈$38,000 in costs); messages missing 2017–2022; fee order dated Oct. 31, 2025.