In the weeks after the New York Knicks traded Charles Oakley to the Toronto Raptors in 1998, head coach Jeff Van Gundy kept invoking what he called “the ghost of Charles Oakley.” The Knicks were trying to move forward, but Van Gundy believed something irreplaceable had left with the franchise’s emotional heartbeat. “When the ball’s driven into the paint, when there’s a loose ball on the court, we have to make up for what was lost,” Van Gundy said at the time.

Nearly three decades later, that ghost hovered over the happiest night in modern Knicks history. As New York celebrated its first NBA championship in 53 years at Frost Bank Center, Oakley watched from courtside. Yet according to ESPN’s Stephen A. Smith, one of the franchise’s most beloved figures still felt separated from the moment.

“I was at the game Saturday night, and there was one thing and one thing only that was incredibly, incredibly sad. And that was Charles Oakley being in attendance,” Smith said on First Take.

“I was there with Charles Oakley. Charles Oakley is one of the great Knicks.” Smith then revealed what struck him most about the championship night. “And the reason why this hit me so hard, I went over, and I sat next to him, and I talked to him. I’m telling you what my perspective is. I ain’t gonna tell anybody what he said. I’ll tell you what my perspective is. The brother was hurt,” Stephen A. pointed out.

Smith’s comments centered on one uncomfortable reality: while former Knicks legends such as Patrick Ewing, John Starks and Allan Houston celebrated alongside the franchise, Oakley watched from a distance despite being in the arena for the title-clinching victory.

“To know what this man meant to the New York Knicks, and for him not to be beyond that ticker tape that carted off everybody, he wasn’t able to get with it. No, he wasn’t.”

So, Stephen A. Smith declared, “I literally have to say on national television, Charles Oakley, we love you, bro. We love you. And not only that, those players love him.” The present New York Knicks team and the fans would love to have the legend walk into the Garden once again. However, the biggest hurdle on the way is James Dolan.

“You got James Dolan there because of the friction that happened with him and Charles Oakley. You can’t let it go,” Smith pointed out. “Mr. Dolan, here on national television, I’m going to tell you something that would exponentially help your image. If you care, which I sincerely doubt, but if you care, something that would significantly help your image, let it go.”

Oakley’s standing within Knicks history helps explain why Smith reacted so strongly. The former forward spent 10 seasons in New York and became the physical embodiment of the franchise’s rugged 1990s identity. When the Knicks traded him in 1998, Van Gundy admitted the departure was “very difficult” because of what Oakley had meant to both the team and his own coaching career.

Oakley’s influence extended far beyond statistics. He protected Patrick Ewing, set the tone defensively and became one of the most respected enforcers of his era. Former teammate Doc Rivers later summed up Oakley’s place in Knicks culture when he reacted to the 2017 Garden incident by saying, “That’s my guy.”

Moreover, Oakley is a part of the Knicks royalty until his rift with boss James Dolan changed everything. Since Oakley’s removal and arrest at Madison Square Garden in 2017, his relationship with Dolan has remained fractured. Oakley has repeatedly maintained that any return to Madison Square Garden begins with an apology from Dolan.

Charles Oakley’s broken relationship with James Dolan

While MSG security removed Charles Oakley from the stands, the crowd chanted, “Oakley! Oakley!” In his incident in 2017, the 62-year-old faced three assault charges. Moreover, authorities revoked his entry to the Garden. After his release from the Midtown South Precinct, Oakley spoke to the media about the incident. “What happened is me and four friends went to the game tonight, to watch the Knicks and Clippers. We did sit down, trying to have a good time. Next thing I know, I was asked to leave the building,” the Knicks legend said.

“I asked, ‘Why?’ and they said, ‘You have to leave because someone ordered you to leave.’ And I’m like, ‘I’ve been here four and a half minutes,”’ he shared. Oakley added, “I’m a Knicks fan, played here 10 years. I love the Knicks. I love New York. This is my heart. I wish them all the luck and success on the basketball court. I don’t know why I’m not welcome into the Garden.”

The scene immediately sparked backlash inside the arena, with fans chanting “Oakley! Oakley!” as security escorted the Knicks legend away. Even then-Clippers coach Doc Rivers, a former teammate of Oakley’s, admitted he nearly ran onto the floor during the incident. “That was tough for me to watch,” Rivers said afterward. “That’s my guy.”

Meanwhile, authorities reported that three arena staff members sustained minor injuries during the incident involving Charles Oakley. Although the Knicks quietly eased the ban that had kept him away from MSG a year later, the franchise legend chose not to make a return. “I guess their lawyer called my lawyer saying it’s a good time for you to come back to the Garden,” Oakley said in 2024. “They’ve got to apologize. We’ll go from there. Can [Dolan] be man enough to say, ‘Mistakes happen.’ And he made one.”

The Knicks finally ended a 53-year championship drought, bringing together generations of players and fans who had waited decades for the moment. Yet even amid the confetti, one of the defining figures of the franchise’s modern history remained separated from the celebration. Nearly three decades after Van Gundy warned about the “ghost of Charles Oakley,” that absence was still impossible to ignore, and it is what prompted Stephen A. Smith to tell the Knicks legend, on national television, “We love you, bro.”