Michael Jordan Forged a Bond With Charles Oakley Through a Prophetic Act of Kindness

When you hear the name Michael Jordan, a very specific image probably comes to mind. Whether you think of his time on the hardwood or any of his extracurricular activities, MJ is a fierce competitor. There is no time for sweet talk or kind words during the heat of the moment; it’s all about the relentless pursuit of the top spot.

And while there may be an element of truth to that, it is not the whole of the story. Consider, for example, an interaction His Airness had with a young Charles Oakley.

During the big man’s first season in Chicago, he had nothing to do during the All-Star break. Realizing this, Jordan, in a prophetic move, invited him to enjoy the NBA’s festivities with him. From there the rest was history.

Michael Jordan thought a lot of a young Charles Oakley and showed some kindness to the forward Michael Jordan and Charles Oakley from their first season together. | Raymond Boyd/Getty Images

During his time in the Association, Jordan’s most famous running mate was Scottie Pippen. In the Windy City, however, His Airness also formed quite the bond with Charles Oakley.

As documented in a 1986 Chicago Tribune piece, Jordan, still relatively new to the NBA scene, formed a bond with the rookie. In fact, MJ quite extended the gesture to the former Virginia Union man.

“Take one look at who Michael Jordan is escorting around on All-Star weekend and you’ll understand a little more about the man who is the heart of the Bulls,” wrote Bob Sakamoto. “… But instead of being arm-in-arm with a beautiful woman, Jordan is side-by-side with Charles Oakley. Jordan led the voting for the Eastern Conference team, but a broken foot he suffered in the third game of the season would keep him home until the NBA persuaded him to appear for public relations reasons. They rewarded him with an everyday weekend for the guest of his choice, and he invited Oakley, the Bulls’ rookie.”

However, that was not the end of the story. Jordan had some kind words for his protégé.

Last week I asked him what he was doing over the All-Star break. He didn’t know what to do, being a newbie and all. I felt sorry for him. I told him to come with me and that he didn’t have to pay for anything. I made sure everything was taken care of. He’s a really nice guy. I like Charles Oakley. It will give him something to look forward to in the coming years, a goal unto himself. He will see all the best players in the league, and one day he might play here. It’s an experience, something you can cherish after you’re older.

Michael Jordan

And as if that wasn’t kindness enough, MJ pushed even further. As well as calling Oak his “bodyguard”, the Chicago Bulls star explained how he wanted to take care of the forward alongside everyone else in the locker room.

“This is my bodyguard,” Jordan added. “I’m going to be like a big brother to him. We have a good relationship, and that’s how the whole team should be. One person must take care of another person. We have to learn to help each other in bad situations.”

Oakley certainly seemed to appreciate Jordan’s efforts

In Sakamoto’s article, we never heard from Charles Oakley himself. However, based on everything we know, it’s safe to assume that he appreciated what Jordan did for him.

While the couple’s time together didn’t last too long, Oak spoke about his affinity with MJ. After The Last Dance, for example, the forward explained that he and the living legend simply clicked.

“We got to be friends, and whenever I called, he answered the bell,” Oakley explained. “The thing about me and Mike, we talked trash to each other, but we never crossed the line. There is so much respect. We are just tight. We don’t fight. We don’t do this or that. We are 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.”

That connection eventually brought the big man to Washington, DC, where he reunited with his old partner. And even in retirement, the “bodyguard” still comes to the aid of His Airness. During a 2022 appearance on All the Smoke, for example, the Cleveland native had no problem going after Isiah Thomas.

“He [Jordan] said a lot about a lot of people,” Oakley said at the time. “… Isiah spoke about himself. Don’t like Isiah anymore. I don’t know what’s going on with Isiah. He’s just too sneaky. He always says, ‘I don’t do it,’ but he did it. It’s like, ‘We’ve got you on camera; you did it.’ He still wants to be Mike. Mike doesn’t want to be your friend, Isiah. I’m telling you for the fifth time. He doesn’t want to be your friend. Stay on ESPN. Keep talking on TNT. Now you try to say everyone better than Mike. It’s OK. You are no better than Mike. He came to your city and took your city. That’s why you’re really mad: He took over Chicago. I know.”

It is also worth noting that, in addition to the fact that Jordan’s gesture seemed to strike a chord with Oakley, His Airness was also correct in his judgment. He hoped the All-Star trip could inspire his teammate to earn his way onto the big stage, and Oak Tree did just that in 1994.

Is MJ always the nicest guy? No, but he was definitely on to something by taking Charles Oakley with him to All-Star Weekend.