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Oakley wasn't aware, but according to another MSG security source there were discussions about tracking Oakley, even as he traveled hundreds of miles away. “They wanted to have us doing covert surveillance operations on him,” the source says, referring to Oakley, “just to see where he was at, what he was doing at the time, to try to dig up something to use.” As a series of court cases would later allege, the Garden security’s staff viewed the surveillance of perceived enemies as a normal part of doing business.
Oakley was one of the few people willing to talk on the record. Years ago, he claims, he was attending a game at MSG with his friend Anthony McNair. His former Knicks teammate, Hall-of-Famer Patrick Ewing, was the associate head coach on the opposing squad, and sought out Oakley before tip-off. The pair embraced, chatted briefly, and made plans to talk at the game's conclusion. Oakley and McNair said they were soon approached by security, who informed Oakley he wasn't allowed to stray from his seat or venture into areas where fans are restricted. After the final buzzer, Oakley met Ewing alone near the visitors’ locker room. There, according to Oakley, Ewing warned him about talking because listening devices were everywhere. “Don't talk too loud,” Oakley said Ewing told him. “This place is supposed to be mic'd up.”
"Don't talk too loud," Knicks legend Charles Oakley recalls Patrick Ewing saying. "They got the whole building mic'd-up." Then, a source tells us + @WIRED , Garden security discussed tracking him across America. And that's just the start of our new collab on MSG's deep state. 🕳️🐇
"Don't talk too loud," Knicks legend Charles Oakley recalls Patrick Ewing saying. "They got the whole building mic'd-up."
— Pablo Torre Finds Out (@pablofindsout) April 17, 2026
Then, a source tells us + @WIRED, Garden security discussed tracking him across America.
And that's just the start of our new collab on MSG's deep state.… pic.twitter.com/aveI3O6NXx
Charles Oakley, the legendary Knicks forward known as the toughest man in the league recalls that Trump was a constant presence in that scene. I spoke with Oakley by phone throughout the afternoon and he told me that he remembers Donald Trump being around New York City and very cool with NBA athletes and other celebrities back then when he was a media mogul and worked in travel long before he became President of the United States. On this particular night the elevator at the Grand Hyatt was crowded. Inside stood Trump and Jayson Williams who was a 6’10” powerhouse for the Nets and Oakley. When the doors opened, Kobe Bryant walked in.
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That search for respect hit a wall in the Grand Hyatt elevator. As the story goes Jayson Williams offered a casual greeting to the young Bryant. Kobe, perhaps distracted or simply possessing that singular aloof focus that would define his career gave a dismissive nod or a short response without making eye contact. Bryant was reportedly listening to a Walkman and while he heard the greeting he merely shrugged and slurred “Hey big man” without looking up. In the “Old School” code of the 90s NBA this was a cardinal sin. Williams was a man whose career was defined by both immense talent and a hair trigger temper and he took it as a personal insult. According to witnesses Williams lunged and shouted “Are you f—-n’ kidding me?” before landing a punch to Bryant’s cheek.
The confined space of an elevator is the last place you want to be when a 270 pound professional athlete decides to throw a punch. Williams reportedly swung at Bryant and the situation threatened to turn into a full blown brawl between a veteran who felt disrespected and a teenager who refused to back down. This is where the story shifts from a standard locker room scrap to a surreal piece of history. Donald Trump standing between the two giants didn’t head for the corner. He stepped into the fray. Trump later confirmed the lore during an interview with Jake Paul by stating that he was breaking up a fight. He noted that breaking up a fight is sometimes more dangerous than being in one. He liked Kobe and saw that Kobe was having a hard time with somebody but it worked out fine. Trump physically intervened and grabbed Williams and told Kobe to get out of there quickly. The doors opened and Bryant exited and a potential disaster for the NBA’s rising star was averted by the man who would eventually occupy the Oval Office. Interestingly when I spoke with Charles Oakley he mentioned that while he was there he does not personally remember the specific details of this elevator fight. However he noted that Jayson Williams tells the story often and he emphasized that Jayson is an awesome storyteller who brings these moments to life with incredible detail.
Former New York Knicks star Charles Oakley must pay more than $642,000 in lawyer fees to Madison Square Garden for deleting text messages during a court battle over his ejection from a game eight years ago, according to court documents. The 61-year-old former power forward — who filed a defamation lawsuit against the arena firm and its CEO James Dolan in September 2017 — is accused of sending the company’s high-priced attorneys on a wallet-busting wild goose chase.
Charles Oakley on Shaquille O'Neal: Shaq… I mean, Shaq is Shaq. He big. I didn't never take Shaq as a tough guy. I think they more tougher now on TV than they played. When Shaq always complains about guys fouling him, this and that, you’re 350 pounds. I mean, what are they going to do? Shaq is all right. We had a couple of little run-ins. I mean, I straightened him out. One time, he crossed the line and it was me and Michael Jordan, we were together in New York. We was in the Palace Hotel and MJ went to get some coffee. I was checking out and I saw him and I walked up to him like, you've been disrespectful, right? Him and his uncle were together. I said there was some BS you did. You crossed the line with me. This and that. He had called me out. MJ ran and said oh, what you doing, man? I said he crossed the line, man. He knows what he did. So MJ pulled me away. I guess cuz they frat brothers, but and I told him what happened. He's like, ‘Yeah, that’s f*cked up.’
Jorge Sierra: Pascal Siakam passed all these players in playoff scoring today: Anthony Davis Adrian Dantley Jerome Kersey Jrue Holiday Charles Oakley He's No. 117 all-time now.
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In an interview with former NBA player Jim Jackson, Charles Oakley was asked what it would take to get him to make peace with ownership and return to the Garden. Oakley largely blamed Patrick Ewing for him not being welcomed back.
“Even though all them guys [are] going back, I really can’t blame all them guys, because I didn’t really play with all of them,” Oakley said. “The ones I played with who got some power, I thought would be Patrick, but he didn’t step up. So I hold him more responsible than anybody else, because he’s supposed to be our franchise players. I played with him for 10 years...He haven’t spoke up yet, so I’m gonna let it just play out.”
Charles Oakley: “I would love to be there. I know the fans would love me to be there. I love the fans. They gave me a lot of cheer over the years, but it all started from the Commission[er Adam Silver], the owner and all other owners in the NBA, because he making it bad for all the teams in the league for something like this to be going on for eight years.”
The Knicks have opened the door. The ball is in Charles Oakley’s court. They would welcome him back with open arms as a celebrated team alumnus if he drops his lawsuit against owner James Dolan and Madison Square Garden, a source with knowledge of the situation told The Post.