On February 8, 2017, Oakley was involved in an altercation at Madison Square Garden as the Knicks faced the visiting Los Angeles Clippers. According to the Knicks, Oakley was ejected from the arena after he is alleged to have yelled at James L. Dolan, the Executive Chairman of Madison Square Garden and MSG Networks, and refused to stop, an allegation he denies. There were also accounts of him hitting a security guard in his face and shoving another guard before being dragged away from the game and handcuffed. He was charged with three counts of misdemeanor assault and criminal trespassing. In a statement, the Knicks stated that Oakley "came to the game tonight and behaved in a highly inappropriate and completely abusive manner. He was ejected and was then arrested by the New York City Police Department."