- - Federal Judge Rejects James Dolan’s $1.5M Demand In Charles Oakley Legal Battle

Caroline JohnNovember 4, 2025 at 7:00 PM

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Aug 17, 2019; Dallas, TX, USA; Killer 3s head coach Charles Oakley during the game at the American Airlines Center. Mandatory Credit: Jerome Miron-Imagn Images ©Aug 17, 2019; Dallas, TX, USA; Killer 3s head coach Charles Oakley during the game at the American Airlines Center. Mandatory Credit: Jerome Miron-Imagn Images

The Charles Oakley vs the Knicks war took a turn that may not be unexpected. As it tends to happen when the Knicks is feuding with its own players, it ended poorly for the player. Oak had upped his legal fight against Madison Square Garden in February. The Garden issued a statement that they’d welcome him back if he dropped the lawsuit but resolution was nowhere in sight. Now Oakley’s facing the punitive consequences of an eight-year long legal battle. But it’s not a total win for James Dolan.

According to reports, U.S. Magistrate Judge Robyn F. Tarnofsky ruled against the NBA legend last week. Oakley owes MSG $642,000 in attorney fees. It’s small consolation that the compensation sum is six figures.

The Garden’s lawyers at King & Spalding had sought more than $1.5 million in fees. The judge rejected that figure and instead reduced the amount by almost a million.

It, of course, stems from the infamous 2017 incident with Knicks and MSG owner, James Dolan. Oakley was ejected from the stands during a game. Both sides have conflicting stories and accused each other of defamatory statements. That case took an unusual turn this year resulting in Oakley’s recent defeat.

In an amended complaint from April 2024, Oakley’s camp made claims of assault and battery against the stadium and its related entities. His lawyers then said in August 2024 that the NBA legend had lost all text messages he had sent or received between February 8, 2017, and February 2022 when he upgraded to a new device.

“The court concludes that Oakley’s loss of his text messages cannot be credibly explained as involving anything other than bad faith,” U.S. Circuit Judge Richard Sullivan said in the July order. While the federal court is putting the burden of his mistake on him, Oakley is far from taking it on the chin.

Charles Oakley is determined to extend the fight

Oakley had claimed he didn’t know he had to preserve the texts and alleged his lawyers didn’t advise him about it. Note: under the Federal Rules of Civil Procedure, parties in litigation have a legal obligation to preserve evidence—including texts and other data from phones—related to claims and defenses. When parties fail to undertake reasonable efforts to preserve evidence, they can be issued what are known as ‘spoliation sanctions.’

These five years’ worth of text messages could have been used as evidence in the lawsuit Oakley filed over his ejection MSG in 2017. MSG’s lawyers claimed that AT&T, Oakley’s mobile carrier, revealed that retired forward sent and received 7,770 texts in the three-week span since his forced removal from the arena. Those texts could’ve provided context to the personal grievances between Oakley and Dolan. The Knicks legend had been critical of the billionaire’s management before the incident.

MSG’s legal team was seeking these texts through subpoenas to prove Oak’s state of mind behind his animosity with Dolan. They reportedly felt Oakley owed them $1.5 million in reasonable attorneys’ fees and costs in seeking the spoliation motion and “pursuing discovery related to Oakley’s loss of text messages.”

The judge noted that Oakley had previously upgraded his phone without losing these texts. As a result, the judge sanctioned him. Should the case go to trial, the spoliation sanctions could be presented to the jurors which would adversely affect Oakley’s case.

In response to the $642k verdict, Charles Oakley’s lawyer issued a scathing statement. Valdi Licul, a Wigdor partner, said they “disagree that MSG is entitled to any recovery and will promptly seek to appeal.” His lawyers alleged the sum should be either $0 or no more than $45,538 in fees and costs.

In something out of a courtroom drama, the legal documents indicate Oakley’s attorneys and the 2024 judge engaged in a debate about the MSG lawyers’ hourly fees and how this grudge match has devolved into a game of torts.

MSG is yet to respond to the decision. However, this is nowhere near a conclusion both sides are going for. Oakley and MSG have pending sanctions against each other amid allegations of making false statements.

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Source: “AOL Sports”