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Charles Oakley Reaches Plea Deal With MSG Prosecutors but Civil Action may Remain

Charles Oakley agreed to stay away from Madison Square Garden for one year. SI's legal expert examines what may still come from his dispute with James Dolan.

Don’t expect to see Charles Oakley at Madison Square Garden anytime soon. But don’t expect the high-profile dispute between the 53-year old former New York Knicks star and Knicks owner James Dolan to end anytime soon, either.

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On Friday, Oakley and Manhattan prosecutors reached a plea deal that calls for Oakley to stay away from MSG for the next year. In exchange, misdemeanor assault and trespass charges against Oakley have been—tentatively—resolved. Those charges were brought after Oakley’s much-publicized altercation at a Knicks-Los Angeles Clippers game in February with two MSG employees. Oakley threw punches and caused minor injuries. Oakley’s scuffle stemmed from his ongoing dispute with Dolan, whom Oakley contends has disrespected him in recent years. During the game, Oakley allegedly heckled Dolan, who was sitting nearby, and others sitting around Dolan. Oakley is said to have used profanities as part of his heckling.

The condition that Oakley avoid MSG doesn’t appear to be a meaningful concession. Oakley’s attorney, Alex Spiro, said on Friday that his client hadn’t planned on going to MSG anyway.

Oakley’s plea deal also calls for him to avoid engaging in any criminal behavior for six months. If Oakley violates the terms of his plea deal, the criminal case against him would be restored.

Charles Oakley Banned From Madison Square Garden for One Year After Plea Deal

While there is tentative closure to the criminal law aftermath of Oakley’s MSG scuffle, the possibility of civil law ramifications remain. Spiro told media on Friday that Oakley reserves the right to pursue a lawsuit against Dolan, MSG and the Knicks.

So what might Oakley and Spiro have in mind?

As a starting point, MSG clearly had the legal right to demand that Oakley leave the game and the legal right to apply reasonable means of compelling Oakley to exit.

Tickets to NBA games constitute what are known as “revocable licenses.” A game ticket provides a legal right to a person to enter an NBA arena and sit in a particular seat in order to watch an NBA contest. Without that license, a person in the arena would be committing trespass. If the ticket holder violates the terms of the license the arena can revoke the license and order that the ticket holder leave the arena immediately. Disturbing the peace of other ticket holders is one ground that can trigger revocation.

As a result, whether Oakley was morally justified in confronting Dolan isn’t a relevant legal point in assessing Oakley’s behavior. Available video evidence suggests that Oakley clearly disturbed the peace. He thus had an obligation to leave MSG.


But Oakley “having to” leave MSG doesn’t mean MSG employees could compel Oakley to leave in any way they saw fit. Here is where Oakley might have a viable case. Oakley’s removal had to be reasonable under the circumstances. The methods employed by MSG security should not have caused Oakley undue harm or needless embarrassment. If Oakley believes MSG security behaved unreasonably, Oakley could sue MSG for various claims, including negligence, battery, false imprisonment and intentional infliction of emotional distress.

On the other hand, the more aggressive and dangerous Oakley seemed upon the revocation of his license, the harder it would be for him to argue MSG employees behaved unreasonably. So how would a jury interpret the situation? The fact that there is ample video and audio evidence, as well as numerous potential witnesses, would allow a jury to consider a very thorough account of what took place.

In addition to suing MSG over his removal, Oakley might also consider suing Dolan and the Knicks for defamation.

Dolan has made a number of public remarks about Oakley that are, to put it charitably, insulting. In a February interview on The Michael Kay Show, Dolan described Oakley as suffering from “personality problems” that include “anger” issues. Dolan also insisted that Oakley is “both physically and verbally abusive.” Further, Dolan implied that Oakley might suffer from alcohol problems. For their part, the Knicks public relations’ department released what might be viewed as a condescending or suggestive of Oakley suffering from a medical problem. The team said “we hope he gets help soon.”

Oakley could assert these remarks were designed to harm his reputation and ridicule him. Oakley, however, would face several legal hurdles.

First, truthful statements are not defamatory. Therefore, if Dolan was correct that Oakley suffers from various personality problems, Dolan’s statements wouldn’t have been unlawful. To be sure, those remarks may have been degrading. And one could argue that those remarks were completely inappropriate, especially when voiced by an NBA owner in reference to a popular former player on that owner’s team. But if those statements were true, then Dolan wouldn’t have broken the law by saying them.

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Second, Oakley is a public figure, meaning he would need to prove “actual malice:” that the statements about him were not only untrue but that Dolan knew the statements were untrue. If Dolan could establish that he genuinely believed Oakley suffered from diagnosable personality problems, then even if such a belief proved unfounded, Oakley likely wouldn’t be able to show Dolan acted with actual malice.

Third, defamation requires specific and factual statements, rather than statements of opinion. Dolan might contend that his descriptions of Oakley were just amateurish takes and shouldn’t be regarded as authoritative or based on any professional training.

The most likely outcome? Oakley and Dolan reach an out-of-court resolution to their dispute. It seems everyone believes their quarrel makes both of them look bad. Certainly NBA commissioner Adam Silver, who has previously tried to negotiate a peace deal between Oakley and Dolan, would urge a resolution that removes the dispute from the limelight and preempts litigation. Silver, an attorney by trade, knows that if Oakley-Dolan litigation commences, the risk of pretrial discovery would surface. Pretrial discovery would include sharing of evidence and sworn statements. It might lead to damaging evidence about both Oakley and Dolan and perhaps others, too.

Sometimes the best approach is for cooler heads to prevail. We’ll see if that happens.

Michael McCann, SI's legal analyst, provides legal and business analysis for The Crossover. He is also the Associate Dean for Academic Affairs at the University of New Hampshire School of Law.