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It’s been eight years since Charles Oakley was forcibly removed from a Knicks game in handcuffs and hit with criminal charges during an incident that led to him filing a lawsuit against James Dolan and the team. However, that ended up being a costly decision when you consider he’s been ordered to cough up a hefty sum after deleting text messages he sent in the wake of his arrest.
Charles Oakley spent the majority of his 19-year NBA career with the New York Knicks, and the big man played an integral role on the team that made the playoffs every single year he was on the roster—including a run to the NBA Finals in 1996 that ended with them losing to the Hawks in seven games.
Oakley was traded to the Raptors a year before owner James Dolan took an increased interest in the day-to-day operations of the franchise, and he is one of the many people who have not been shy about voicing their displeasure with the direction the team has headed since he decided to inject himself into management decisions.
In 2017, their feud hit a tipping point when Oakley headed to Madison Square Garden to watch the Knicks host the Clippers on February 8th.
According to his account of that night, Dolan (a noted authoritarian who rules the iconic venue with an iron fist) spotted him in the stands before instructing security to remove him, and the former All-Star was charged with assault and trespassing after declining to exit in a peaceful manner.
The following week, Adam Silver recruited Michael Jordan to help mediate a sit-down where Oakley and Dolan agreed to a truce, and the latter (who claimed the former had verbally accosted him before the physical altercation unfolded) lifted the ban he’d levied in the wake of the incident.
However, Oakley filed a civil lawsuit later that year, and that decision has come back to bite him based on the most recent development.
A judge has ordered Charles Oakley to pay James Dolan and the Knicks $642,000 for deleting text messages linked to his arrest at Madison Square Garden
Oakley decided to take Dolan and the Knicks to court in September of 2017 while accusing the franchise of defaming him by falsely accusing him of assault and issuing a statement that implied he had a drinking problem.
The two parties have spent more than eight years going back and forth while attempting to squeeze damages out of each other, and on Friday, things took another turn after a judge hit Oakley with a stiff penalty over five years’ worth of text messages he said he was unable to provide to the opposition’s legal team because they were deleted when he upgraded his phone.
According to Front Office Sports, attorneys representing Dolan and MSG argued they spent $1.5 million in an unsuccessful attempt to recover the texts in question. The judge declined to award that amount, but Oakley was nonetheless chided for failing to retain the texts and ordered to pay a grand total of $642,337 in legal fees.
As the outlet notes, he did make around $44 million in contract earnings alone during his time in the NBA, but that’s still a pretty hefty amount. One of his lawyers said they will appeal the ruling, and it doesn’t seem like the case is going to be settled anytime in the near future.