Charles Oakley, MSG Still Sparring as Judge Weighs Dolan Testimony

A federal judge in New York last Thursday issued a mixed set of rulings in retired New York Knicks star Charles Oakley’s long-lasting litigation against Madison Square Garden Networks over Oakley’s removal from his seat at a Knicks game in February 2017. The rulings indicate that unless the parties reach a settlement, a dispute that began shortly after Donald Trump became the 45th president could last well into Trump’s term as the 47th president.

U.S. District Judge Richard J. Sullivan sided with MSG on its demand that MSG chairman James Dolan face deposition only after MSG personnel are deposed. Sullivan agreed with MSG that having Dolan go last would help to “narrow the scope” of Dolan’s deposition. The judge reasoned that MSG employees “who were directly involved in Oakley’s removal and thus have the knowledge most relevant to determining whether unreasonable force was used against Oakley” should go first.

The fact that MSG employees haven’t yet been deposed is partly a reflection of the litigation’s turbulent path. The case has been dismissed twice at the trial level but reinstated twice by the U.S. Court of Appeals for the Second Circuit, meaning it’s now in round three at the Southern District of New York. There are also disputed questions about key testimony and evidence that could further bog down the case. In the current version of the litigation, Oakley’s civil case is related to assault and battery claims stemming from his removal.

While Sullivan agreed Dolan would face deposition after MSG personnel, he sided against MSG’s request that Dolan not face deposition at all. 

The judge explained that Oakley’s assault and battery claims “ultimately boil down to two considerations.” The first is the amount of force MSG staff used to remove Oakley from the Garden and, second, whether that force “was objectively reasonable under the circumstances.” 

Oakley believes Dolan instructed staff to remove him. Sullivan reasoned that Dolan’s potential testimony is relevant in that he would have to answer under oath about whether he instructed—by words and/or “hand gestures”—the security guards to push Oakley and use excessive force. If Dolan gave an instruction to use force, his testimony, Sullivan wrote, “would support the reasonable inference that the guards followed Dolan’s instructions and would therefore make it more probable that the guards did in fact push him.”

Sullivan further observed that Dolan’s testimony is relevant to a key factual question: Whether the security guards “only resorted to force after Oakley physically escalated the situation.” Oakley’s case would be hampered by a finding that he instigated the altercation, since, Sullivan explained, “it might have been reasonable for the security guards to use greater force if Oakley was behaving aggressively.”

The judge was similarly unpersuaded that Dolan ought to be exempt from deposition on account of the apex-witness doctrine. As Sportico detailed in September when Sullivan rejected MSG’s earlier attempt to invoke this doctrine, high-ranking executives are sometimes exempt from depositions since they lack personal knowledge of key facts. In his latest ruling, Sullivan said Dolan “is not the prototypical apex witness who sits in the knowledge or involvement in the underlying conduct.”

Instead, Dolan literally “had a courtside seat to the action” and is accused of being involved in the incident. “The apex doctrine is plainly inapplicable here,” Sullivan insisted. 

Sullivan also disagreed with MSG that Oakley is merely trying to depose Dolan to harass him. MSG cites text messages sent to Oakley from people urging the former player to go after Dolan, with one text saying Oakley should “sue the [expletive] out of Dolan.” Another text encouraged Oakley to use the discovery process to inflict a “public relations, social media, [and] social responsibility toll.” With negative attention stemming from the case, MSG might be more inclined to cut a deal. Sullivan didn’t find this evidence indicative of an intent by Oakley to harass, as there’s no evidence Oakley responded or otherwise endorsed the texts.

“We are pleased that the Court denied James Dolan’s latest attempt to avoid being deposed in this case,”  Wigdor Law partner Valdi Licul, who is one of Oakley’s attorneys, told Sportico in a statement. 

In September, the two sides told Sullivan their “present best estimate” was that a trial would take a couple of weeks. The judge at the time indicated there would be a post-discovery conference on March 4, 2025, though the parties’ recent disagreement about discovery suggests the case has a long way to go.

(In the next-to-last paragraph, Wigdor Law amended its original statement, replacing “to be excused from deposition in this case” to read “to avoid being deposed in this case.”)