Oakley, a longtime NBA enforcer and rebounding machine, said Dolan was wrong to mouth off at a fan who told him to sell the team during a loss at MSG.
Oakey knows as well as anyone what it's like to get ejected from the Garden, not just by the refs. His criticisms of the team and management have led to a strained relationship with the organization, which boiled over in 2017 when he was arrested after an altercation with security officials after they told him to leave his seat at the arena near Dolan. Oakley was cleared of misdemeanor assault charges last year.
"He just tries to bully everybody, and it just don't make sense," Oakley told The Associated Press on Monday.
Oakley was angered by Dolan's reaction after New York lost on Saturday and a fan yelled at the owner to "sell the team."
"You really think I should sell the team?" Dolan said on video run on TMZ. Dolan asked the fan if he wanted to come to any more games, called him "rude," and told him to "enjoy watching them on TV."
Dolan called for security, though it's not clear whether the fan has been actually been banned from games.
"Our policy is and will continue to be that if you are disrespectful to anyone in our venues, we will ask you not to return," the Madison Square Garden Company said in a statement.
Oakley wasn't having it from Dolan.
"He just bullies people because he has money and power," Oakley said.
The 55-year-old Oakley played for the Knicks from 1988 to 1998, helping them reach the NBA Finals. He attended games a few times a year, buying his own tickets because he was no longer comped or invited to official team functions. But his relationship with the franchise was frayed even before the 2017 altercation that included his hitting one security guard in the face and shoving at least one other before he was dragged away and handcuffed.
Dolan lifted Oakley's ban from MSG shortly after meeting with Oakley and NBA commissioner Adam Silver. Oakley said nothing was really settled in the meeting.
Oakley said there was little reason for any reconciliation with Dolan.
"Why would I want to do it with someone who had me dragged out of the Garden for no reason," Oakley said Monday. "Why would I want a relationship with him? I told him I wasn't happy."
The Knicks are 13-54 and in last place in the Eastern Conference and have been one of the worst teams in the NBA over the past 20 years.
"I'm allowed in 29 arenas except the Garden," he said. "They've said, 'We'd retire your jersey,' they'll do this. But you think I want my jersey hanging outside the Garden? They can still see it. But you just dragged me outside the ... Garden."