“It hurt him from the heart” – Michael Jordan was devastated when Charles Oakley got traded by the Bulls

There might have been plenty of ups and downs throughout his basketball career, but Michael Jordan could be satisfied with playing for the Chicago Bulls, knowing that he had a real friend in Charles Oakley .

Both of them arrived at the franchise's humble beginnings in the mid-80s and instantly shared a blossoming friendship. While Michael symbolized greatness and grace for the Bulls, there was Charles, who defined toughness and physicality. Whenever and wherever Michael goes, chances are high that Oak is following him. From both on and off the court, MJ had no worries to think of as he knew that his friend was behind to protect him.

But in the summer of 1988, Jordan's world turned upside down. In what was supposed to be a thrilling night as they'll watch Mike Tyson-Leon Spinks heavyweight bout in Atlantic City, reports coincided that Oakley got dealt by Chicago to the New York Knicks. Looking back, the memories of how Michael felt devastated upon receiving the news are still fresh for Charles.

“Mike was upset. I told him, ‘Let’s just the watch the fight and have a good night.’ And that’s what we did,” Oakley revealed . “I didn’t hold no grudge against Jerry [Krause], Jerry Reinsdorf, Michael, nobody. But Michael, it hurt him from the heart. We had just bonded, got real close.”

A heartbreaking deal for MJ

It was truly a heartbreaker for Michael to process that his close pal and ally would part ways and leave him to join the Knicks.

Behind the scenes, the Bulls got the deal done as a necessity. Then-general manager Jerry Krause became intrigued by how the 22-year-old Horace Grant has shown promise in his rookie year. Grant produced solid numbers despite a backup role, and his performance could only elevate if he inherits the starting power forward spot from Oakley. Knowing that the team had a robust chance to improve their presence down low, Krause pulled the trigger by sending Charles to New York for Bill Cartwright.

Yet regardless of whether it'll help the team win in the long run, Michael perceived it as a betrayal by Krause and the Bulls. The organization knew how tight his relationship was with Oak in the past three years, and they witnessed how MJ heavily relied on him when facing the ruthless plays of their opponents , especially the Detroit Pistons ‘Bad Boys.’ Out of this, MJ developed strong animosity towards Cartwright, commanding his teammates not to pass him the ball, which triggered the veteran center at one point .

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Still lifelong friends

In the end, Oakley's departure served as a blessing in disguise for MJ. He learned to be independent in his own right to face his personal and basketball battles. After years of frustration, Michael got over the hump and led the Bulls in beating the Pistons on their way to the NBA’s mountaintop. It was initially difficult, but Jordan gradually learned to embrace Cartwright as a teammate. As such, it paid wonders as the big man emerged as an instrumental piece in clinching the first three-peat of their dynasty.

Although they clashed along the way amid the Bulls-Knicks rivalry in the early ‘90s, both MJ and Oakley still maintained their brotherhood with each other. And in the 2002-03 season in which Michael spent his last year in the league, he gladly recruited Oakley to the Washington Wizards for one last run to revisit their good ol’ days in Chicago.

Despite that unforeseen breakup, Oak couldn't be happier that he still found a lifelong buddy in Michael.

Related: Michael Jordan opens up about his older brother Larry not making the NBA: "He has always been a good player, but he just didn't grow enough"