Michael Jordan and Charles Oakley played together on the Chicago Bulls and Washington Wizards during their NBA careers. While they didn’t win a championship together, the two All-Stars developed a brotherhood and are best friends to this day.
Oakley played with several great players during his career. However, he admitted that Jordan is his best teammate of all time and explained what it’s really like being best friends with Jordan.
Oakley told Jack Green of Betway Insider that he and Jordan have never gotten into a fight because they have too much respect for each other. Oakley said he’s appreciative that Jordan put him in “The Last Dance” docuseries and mentioned him during his Hall of Fame speech in 2009.
“We got to be friends, and whenever I called, he answered the bell,” Oakley said about Jordan. “The thing about me and Mike, we talked mess to one another, but we never crossed the line. There’s so much respect. We’re just tight. We don’t fight. We don’t do this or that. We’re just the best of friends. He put me in The Last Dance, he put me in the Hall of Fame speech, he put me in Space Jam, so I’ll wait for the next show.”
Jordan and Oakley were so close that Jordan was upset when the Bulls traded Oakley to the New York Knicks in the summer of 1988. Chicago acquired Bill Cartwright from New York and Jordan didn’t like the trade since Cartwright was older than Oakley.
However, the trade worked out for the Bulls, so much so that Jordan acknowledged he was wrong about the deal nine years later.
Jordan told SLAM Magazine in 1997 that he was wrong about the Oakley-Cartwright trade. Oakley was Jordan’s protector on the Bulls. Whenever Jordan got clobbered on his drives to the basket, Oakley would fight the player who fouled his best friend, which is why it was difficult for Jordan to see his pal get traded.
However, Jordan found out that Cartwright was the perfect big man for the Bulls.
“I was wrong with the Oakley-Bill Cartwright trade,” Jordan said. “I loved Charles Oakley. He was like a brother to me, and I felt we were giving away too many years by trading a young rebounder for an old guy who hadn’t played a full season. But in terms of what we were trying to get, he was the best. It was the best trade at the time. I still love Charles Oakley, and I loved having him on our team, but in terms of what Bill Cartwright brought to the team, he made a difference.”
Jordan and Oakley went from teammates to rivals. Oakley had no problem fouling Jordan hard when the Knicks and Bulls faced each other. The two teams met in the 1993 Eastern Conference Finals and Oakley and Co. took a 2-0 series lead.
However, Jordan and the Bulls got the last laugh.
Jordan shot the ball poorly in Games 1-3 of the 1993 Eastern Conference Finals. He shot 37.0% in Game 1, 37.5% in Game 2 and 16.7% in Game 3.
However, Jordan bounced back in a big way in Game 4, scoring 54 points on 60.0% shooting.
The Bulls won Games 3-6 to advance to the 1993 NBA Finals. Jordan averaged 32.2 points and 7.0 assists against the Knicks in the ’93 conference finals, while Oakley put up 8.7 points and 10.8 rebounds per game.
Chicago wound up defeating the Phoenix Suns in the 1993 NBA Finals to capture its third straight title, with Jordan winning his third consecutive Finals MVP.
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