It’s hard to know which side to believe, but it is known that Oakley and Dolan have had a strained relationship for years. Here’s a brief look back at Oakley’s history with the Knicks and some of the events that preceded the latest and most embarrassing chapter in their long-running feud.
The good old (playing) days
Oakley played 10 of his 19 NBA seasons in New York and was a fan favorite for his toughness and intensity. From 1988 to 1998, he averaged 10.4 points and 10 rebounds per game, and he helped the Knicks advance to the playoffs every year. Oakley was traded to the Raptors for Marcus Camby in 1998. After three seasons in Toronto, he spent one season in Chicago, where he started his career, one season in Washington and one season in Houston before retiring in 2004.
Knicks assistant coaching position
During the first few years of his retirement, Oakley played golf with his good friend Michael Jordan, opened a steak house in Miami’s South Beach and oversaw a car wash in Yonkers, N.Y. In 2009, Oakley told the New York Times that he was interested in becoming an assistant coach and had mentioned his interest to the Knicks’ team president, Donnie Walsh.
“I think I have a lot to teach these young guys,” Oakley said. “Especially on the defensive end.”
Citing a person with knowledge of Oakley’s conversation with Walsh, the New York Daily News reported that “Oakley went Oakley on the Knicks, criticizing the team’s lack of defensive intensity and preparation.”
The Knicks never hired Oakley.
LeBron James’s decision
In June 2010, with LeBron James about to become an unrestricted free agent, Oakley told a Miami radio station that he wouldn’t try to convince his friend and fellow Ohio native to sign with the Knicks.
“I can’t tell him to go to New York,” Oakley said of James, via the New York Post. “New York treated me bad. . . . When I go to the Knicks games, do you know that they have somebody that follows me around to see what I say to the press? . . . I said maybe Chicago or Miami . I think him and [Dwyane] Wade would be great together.”
During the same interview, Oakley criticized his former Knicks teammate, Patrick Ewing.
“When [the Knicks] lose, they only point at us, never point at Patrick,” he said. “Patrick was our leader as far as press and people who are watching TV, but the Knicks were made of a lot of tough guys and a lot of heart. I think that sometimes we let our heart get in the way instead of playing the game. . . . Patrick could have been more vocal for the team, but he wasn’t. I think that hurt us a little bit.”
Criticizing Dolan’s Knicks
During his one year as an assistant on the Charlotte Bobcats’ staff from December 2010 to December 2011, Oakley criticized Knicks power forward Amar’e Stoudemire, Knicks Coach Mike D’Antoni’s system and former team president Isaiah Thomas.
“Amar’e’s good, he’s good in his way,” Oakley told the New York Post. “He’s a West Coast player trying to translate to the East Coast. And the longer he plays in the East, the more his body’s gonna get damaged, because he’s got to take a beating now.”
Oakley also reiterated that he was open to patching things up with his former team.
“My door is always open to the Knicks,” he said. “I tell them all the time. They said something about I told LeBron to go to Miami. I was like, ‘You all have to be one of the craziest organizations in the world.’ ”
‘Why aren’t you with the Knicks?’
In February 2015, Oakley claimed he tried multiple times to set up a meeting with Dolan, even going through NBA Commissioner Adam Silver’s office, but to no avail.
“Everywhere I talk to people, it’s like, ‘Why aren’t you with the Knicks? and I said, ‘I tried to.’ And they say, ‘What, is it Dolan?’ ” Oakley said, via the New York Post. “I talked to maybe a million people and a million two say he’s a bad guy. . . . I just want him to talk to me. I don’t know if he’s good or bad.”
Speaking at a news conference in New York to promote Zipway, an athletic clothing company founded by his former Knicks teammate, John Starks, Oakley said he had to buy tickets on StubHub when he wanted to watch the Knicks play at the Garden.
“As hard as I played for that [expletive], and he don’t want to talk with me?” Oakley said of Dolan.
70th anniversary celebration
At halftime of this season’s home opener in October, the Knicks honored several former players as part of the franchise’s 70th anniversary celebration. Oakley wasn’t invited. Around that time, Oakley told the New York Times’ Scott Cacciola that he was still open to meeting with Dolan.
“The boss don’t like me,” Oakley said. “I wouldn’t mind having a sit-down dinner with Dolan. I wouldn’t mind cooking him dinner.”Pause.“Might put something in it, though!”Pause.“I mean, I had at least 15 people try to set up a meeting. He won’t meet. I want to sit down to talk to him. I want me and him in a room. And lock the door. Lock that door!”Another pause.“I mean, he can have the police outside the door.”
After Wednesday’s arrest, Oakley probably won’t be having that sit-down dinner with Dolan anytime soon.