Charles Oakley Ordered To Pay $640K For MSG Ejection
Knicks Legend Charles Oakley Ordered To Pay $640K For MSG Ejection Over Deleted Texts

More than 20 years after retiring from the NBA, Charles Oakley’s enforcer ways are still getting him into trouble inside arenas.
The former New York Knicks player has been ordered to pay $642,000 in legal fees to Madison Square Garden, according to Front Office Sports.
The payout stems from a 2017 incident in which he was at MSG to watch a New York Knicks game against the Los Angeles Clippers. While seated near owner James Dolan, witnesses said he got into a verbal altercation with security, and Knicks officials say he was “verbally abusive” to people near the chairman.
What followed was security guards crowding around Oakley, and things turned physical, and the video shows them circling him as he grabs at them while dragging him out of the arena, and even placing him in cuffs.
When the footage went public, fans immediately found it distasteful that MSG would treat one of its legends that way.
The optics only got worse in the aftermath, with the Knicks alluding to Oakley having substance abuse problems, needing “help,” and appearing to be “inebriated” during the interaction.
Oakley, charged with assault, harassment, and trespassing, fired back, claiming that Dolan just didn’t like him.
Even NBA players joined the conversation as LeBron James even had Oakley’s back, while Michael Jordan and NBA Commissioner Adam Silver mediated a private meeting between the two in the days after, but it didn’t seem to help. The charges against Oakley were dropped, though he responded by filing a civil lawsuit against Dolan, claiming defamation, assault, and false imprisonment.
The ruling that orders Oakley to pay up comes from his deleting texts relevant to the case.
“On or around July 10, 2024, [Oakley’s] counsel discovered that all text messages sent to or from [his] phone prior to February 2022 had been deleted,” the court papers revealed, adding that Oakley had “not ever attempt[ed] to preserve, collect, image, or copy [his]personal devices.”
When asked about the missing text messages by Dolan’s lawyer in December 2024, he chalked it up to not being technologically inclined.
“I don’t do well with gadgets and stuff,” he said. “My phone is not that important. I don’t know what the cloud is.”
MSG initially demanded that Oakley pay $1.5 million to cover its legal fees, but the judge did the math and arrived at $642,337.65.
The legal proceedings may be over, but a true reconciliation may be out of reach.