Michael Jordan never made a secret of the fact he was upset when good friend Charles Oakley was traded from the Chicago Bulls to the New York Knicks in 1988. The Bulls and Knicks, of course, became bitter rivals in the years that followed and engaged in some of the most physical battles of all time, particularly in the NBA playoffs, where the two teams met six times in an eight-year span after Oakley was shipped to the Big Apple.

Despite their friendship, Jordan and Oakley did whatever it took to help their respective teams win. For Jordan, that meant taking a lot of beatings in the paint from the Knicks defense. And many of those came at the hands of Oakley as he came up with his own set of “Jordan Rules” that had painful consequences when his good friend didn’t follow them.

Michael Jordan and Charles Oakley played three seasons together with the Chicago Bulls

Jordan and Oakley became teammates in Chicago when the Bulls acquired the draft rights to Oakley from the Cleveland Cavaliers following the 1985 NBA Draft. The two quickly became friends, and while Oakley was the team’s second-leading scorer in his second season, he was also the team’s leading rebounder and one of its best defenders. He also took on the role as somewhat of a bodyguard to Jordan, who had a target on his back every time the Bulls took the floor.

But in 1988, one year after Chicago acquired Scottie Pippen and Horace Grant, the Bulls shipped Oakley to the Knicks in exchange for center Bill Cartwright, a trade Jordan initially hated. But it was a move he had no choice but to live with, and he and Oakley engaged in some fierce battles over the next few years as the Bulls and Knicks became two of the best teams in the Eastern Conference.

Oakley had no problem putting Jordan on the ground during the physical matchups between the Bulls and Knicks

From 1989 to 1996, the Bulls and Knicks met six times in the NBA postseason with the Bulls winning five of the six series, the only New York victory coming in 1994 when Jordan was taking his shot at a baseball career. Despite losing the vast majority of the time, Oakley and the Knicks never made it easy on Jordan and the Bulls and essentially took the title of the most physical team in the NBA from the “Bad Boys” Detroit Pistons in the early 1990s.

And just as the Pistons had their own set of “Jordan Rules,” Oakley also had his own set of rules for the Bulls, particularly for his good friend, as he once told DJ Vlad.

“You come to the paint, I mean that’s my job. His job is outside; mine’s the paint. Some people buy a lot of real estates, some people have little real estate. That little paint is my real estate; outside he can have all that real estate. He [Michael Jordan] knew the rules. It wasn’t like anybody tried to hurt him, but when you come inside, we gotta let you know. You come in my territory now, and I gotta let you know, it’s still the same way, you gotta pay the toll.”

Charles Oakley on Michael Jordan

Go back and watch those old Bulls-Knicks series and it certainly won’t look like Jordan and Oakley were great friends. But that just goes to show how much each was willing to put on the line to win.

The two were later teammates with the Wizards

The last time Jordan and Oakley met in the postseason was in 1996 when the Bulls knocked off the Knicks in five games in the Eastern Conference semifinals on the way to their fourth of six NBA titles. Following Chicago’s final championship run in 1998, Jordan went back into retirement while Oakley was traded from New York to Toronto after spending a decade with the franchise.

Oakley spent three seasons with the Raptors and returned to Chicago to play one more season with the Bulls in 2001-02, the same year Jordan made his return to the NBA with the Washington Wizards. The two were once again teammates in Washington in 2002-03, after which Jordan retired for the final time while Oakley played seven games with the Houston Rockets before retiring himself.