. Oakley was handcuffed and arrested after an altercation with security while sitting near owner James Dolan during a game against the Los Angeles Clippers. Oakley initially brought a number of claims against MSG that were dismissed in February 2020. After appeal, Oakley’s assault-and-battery claim remained.
More on Charles Oakley: Recent HoopsHype Rumors
LeBron James bypassed a reunion with his hometown team for a new opportunity with the 76ers ... so how should Cavaliers fans feel about the rejection?? Ex-NBA star and Cleveland
native Charles Oakley says they should GET OVER IT!! TMZ Sports caught up with Oak at the 17th Annual Amazon Kids Back-to-School Fashion Show in NYC on Thursday ... and asked him all about the 41-year-old King's latest decision to join a fourth franchise. The Knicks great shut down any criticism about James heading to the City of Brotherly Love in pursuit of more rings ... saying what he's doing this late in his career should be admired -- and he's still a role model to young kids. — 8/2/2026 TMZ.com
Charles Oakley: "I was supposed to be on the Roommate podcast. I get a call the day before. They said, we have to cancel you. And then three weeks later, guess who was on there? Dolan. Dolan. I was shooting a commercial right across from the Garden and Cafe 31 and something else. We shot for one day, the next day somebody said, somebody said we had to shut it down. We had permission and everything. So he bullying me around the city, too." — 6/21/2026 YouTube
Charles Oakley: "Brunson is a better Knicks than Patrick." — 6/21/2026 YouTube
Charles Oakley: "Patrick (Ewing) always been like that. He never stood up for nobody. Even when they offered him the D-League job, I said something. And the coldest thing out of this all, I took a case for Patrick on an airplane. Put that out there. I took a case from him. Ask any teammate, Chris Childs, Charles, Allen, John, they might not say nothing, but I took a case to better his self. And this happened to me, he don't say nothing." — 6/21/2026 YouTube
Charles Oakley: I want to talk about the series. I want to talk about the commissioner lying again. When the commissioner is talking about with him and Michael Jordan, he's throwing Michael Jordan under the bus. That's what he's really doing. He's trying to have a conversation like they just talked yesterday. He's coming back out with something from 2017 when we met with that guy from New York, Michael, and himself. And he's trying to act like they tried to solve a problem. And he went to the public in 2017 said we met and we came to an agreement that this is over with. And now you look in the paper he's making another statement about that, but you didn't solve the problem in 2017 cuz it's nine years later and it's still going on. Q. So, Charles, there was no new meeting between you, James Dolan, the commissioner of the NBA, Michael Jordan, nothing like that has happened. Oakley: No. He's lying again. It's two times in this case he has lied about. He lied about putting the statement out that what happened. And he’s lying now like they talked two days ago. No, he didn't. I haven't talked to James, I've been to court with James. And we tried to settle and he said no. So, this has been a whole thing of they ain't blackballing me from the NBA. — 6/5/2026 YouTube
What are your thoughts with the physicality in the league and what you're seeing and just watching Michael Jordan go through that and now with today's NBA where you got to go to a damn review if you blow on somebody. Charles Oakley: Well, I don't think they need to get physical now. I think that they need to get rid of that replay and this and that. If they going to have all that, they might just get two officials. I mean, keep one on each half of the court. But I don't know. The game has changed and it's a new time in life and we got to realize that as you get older, things going to change. But the game changed with the three-pointers. I don't like that. They don't have guys don't have the high IQ, but they get they getting the big money. And I'm glad they're getting the money because they hid the money from us but they got to pay for less talent. — 6/4/2026 YouTube
Rachel Nichols: Adam Silver says both he and Michael Jordan tied their best to broker peace between Charles Oakley and James Dolan, but neither was successful. Oakley has been at Knicks road games during this playoff run but has not been at The Garden. — 6/4/2026 x.com
Mr. Oakley said he has enjoyed watching the play and leadership of the Knicks star Jalen Brunson, who delivered clutch baskets in the Knicks’ Game 1 victory. “Even though me and the owner are in a dispute, I hope the team has success, especially for the city of New York,” he said. “They’ve been waiting for it.” — 6/4/2026 New York Times
But in an interview last week, Mr. Oakley said he had no plans to return to the Garden to watch the finals. On Wednesday, the Knicks won the first matchup in the best-of-seven series against the Spurs in San Antonio. The series will shift to New York for Game 3 on Monday and Game 4 on Wednesday. Mr. Oakley did not say under which conditions he would consider being there. “He started it, he can make it go away,” Mr. Oakley said of Mr. Dolan. “He’s the boss.” — 6/4/2026 New York Times
Louis Williams: "I got to tell you Charles Oakley is he's a urban legend around here. I've heard stories about Oak. Man, give me something good. Give me something good about Oak, man."Derek Harper: "I got something for you. When I first got to New York, I had to be initiated, like we're in college or something. So Oak, (Anthony Mason), John (Starks), all of them. They had me on the elevator in Boston. He tells me, this is the best time for us to do it. I said, do what? Like, what you talking about? He says this is the best time to initiate you. You got to be initiated into the dog pound. I said, man, I hear the little game you all playing. I said, but somebody is going to get hurt. I don't know who, but somebody is going to get hurt. And when I tell you, I've never been locked up like this in a choke hold ever in my life than that particular moment. Because Oak grabbed me and I couldn't move, man. Couldn't move, could not breathe, and was trying to get through it, man. But yeah, Oak and that's a different breed. Ask Antonio and Dale Davis. They'll tell you better than anybody." — 5/27/2026 YouTube
This article originally appeared on Hoops Hype: Judge sides with Madison Square Garden in legal battle against Charles Oakley, 'largely dismisses' case
