'I Tried, Michael Jordan Tried': Adam Silver Admits Failure to Mend Oakley-Dolan Knicks Feud

The roots of this feud go back to the time when Oakley played for the Knicks in the 1990s, when the Dolan family bought the Knicks. Oakley had criticized the way the management was running the team. But the real spark to the feud came decades later.

On February 8, 2017, during a game between the Knicks and the Los Angeles Clippers at Madison Square Garden, an altercation between Oakley and MSG security resulted in Oakley being arrested.

Days later, Silver hosted a meeting at the league headquarters in New York. Jordan joined the conversation over the phone to help calm the tempers of both Oakley and Dolan.

Silver brought Jordan into the situation because the basketball icon had credibility with both sides of the fight. Jordan is a longtime personal friend of Oakley and Dolan’s, and a team owner as well. But despite both Silver and Jordan’s efforts, the two remain at odds

That temporary peace didn’t last, and later that year, Oakley decided to take the matter to federal court. In September 2017, Oakley filed a federal civil lawsuit against Dolan and the Madison Square Garden Company.

Once the dispute entered the legal system, informal league mediation lost all its remaining leverage. Silver made it clear that the commissioner’s office cannot override active court proceedings. 

How a courtside incident turned into one of the NBA’s longest-running feuds

The legal battle has dragged on for 9 years with appeals, dismissals, and legal bills on both sides.

The case took a turn in November 2025 when a federal judge sanctioned Oakley for deleting 5 years of relevant text messages, ordering him to pay MSG over $642,000 in attorney fees. 

The Knicks reportedly offered to welcome him back as a celebrated alumnus with full benefits in May 2025 if he dropped the suit, but he rejected the offer.

Do you believe these two sides will ever find a way to settle their differences outside of a courtroom?