“He don’t care who’s in front of him” - Charles Oakley on facing Michael Jordan, recalls treating him no differently than Reggie Miller or Mitch Richmond on court

Michael Jordan is arguably the greatest player in NBA history in large part because of his competitive spirit and toughness. However, he needed a few years of experience in the NBA before turning into one of the league's toughest players, with a lot of credit going to former teammate and rival Charles Oakley.

Oakley was drafted ninth overall in 1985, one year after Jordan, and was traded to the Chicago Bulls before the season started. He would spend three seasons as an enforcer for Jordan and the Bulls, leading to a long-lasting friendship. In 1988, he would be traded to the New York Knicks, and the Bulls and Knicks would become heated rivals, having physical battles that looked more like a fight than a basketball game.

While playing with Jordan, Oakley toughened the superstar up in practice, being physical with him. As a Knick, Oakley did not care about his friend’s well-being. After writing a book titled “The Last Enforcer,” Oakley went on the Takeline podcast to talk about his book and expenses. When talking about Jordan and their matchups, he said:

“My thing was if he came to the hole, he [Michael Jordan] would get the same as Reggie Miller or Mitch Richmond, or whoever. You know it was my job to shut down the paint. It was great playing with him and then great playing against him, but he was just one of the guys. He don’t care who’s in front of him. He is still going to go out and perform to the best of his abilities.”

Jordan was a pure competitor, and his toughness became a part of that. He always wanted to rise to the challenge and beat any opponent standing in his way. It would lead to him being one of the best basketball players, if not the best, in NBA history.

Michael Jordan’s toughness throughout his career

Michael Jordan at a Charlotte Hornets game

Michael Jordan faced many challenges throughout his NBA career. Due to how athletic and gifted he was, there was often no way to stop him until the Detroit Pistons figured out how much they could rough him up physically.

The Pistons came up with the “Jordan Rules” to stop him. Rule one, try to deny him the ball. If Jordan does not have the ball in his hand, he can’t score. Rule two, if he drives to the paint, foul him as hard as possible. The rules worked to keep the Bulls out of the Finals in back-to-back season, allowing the Pistons to win two straight NBA Finals.

The “Jordan Rules” were brutal. The Knicks would employ similar tactics in their matchups as well. Eventually, Jordan became too strong for the rules, sweeping the Pistons in the 1990-91 Eastern Conference Finals, on the way to his first ring.