“He talked a lot of trash, but he knew he had to pay the toll”: Charles Oakley on Playing With and Against Michael Jordan

Speaking to Draymond Green in The Draymond Green show, Charles Oakley highlighted what it was like, playing with and against Michael Jordan.

Michael Jordan and Charles Oakley
Michael Jordan and Charles Oakley

New York Knicks’ legend Charles Oakley sat down with Draymond Green on The Draymond Green Show to talk about numerous things that happened to him throughout his career, ranging from his draft to many more things, and at one point, the conversation turned to Green asking Oakley about his experience of playing with a young Michael Jordan in the Chicago Bulls, and then playing against Jordan when he was traded to the New York Knicks.

The entire conversation between Charles Oakley and Draymond Green about Michael Jordan

While Green and Oakley were talking about many things, Green turned to asking Oakley about the beginning of his career when he was drafted 9th overall by the Chicago Bulls, which implied that he got to play with a young Michael Jordan, who was as competitive as they come, and what were Oakley’s first impressions of him.

Let’s take a deeper dive into this conversation between them both.

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Charles Oakley outlines his experience playing alongside Jordan

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Jordan and Oakley in Chicago Bulls

At one point in their conversation, Draymond Green said, “… but I also want to get into some of your playing career, and obviously that was… being drafted the 9th overall pick by the Chicago Bulls, which means you then crossover with a very young Michael Jordan…What was your first impressions of Michael Jordan, at that time when you first saw him”, and this question put a subtle smile on Oakley’s face.

When Draymond was done with the question, Oakley said that coming form a historic black college, and getting drafted by a team, his task was to come and work-work-work, and that was the time when he got a chance to meet Jordan, when he was playing pick-up right before training camp. Oakley said that he was always about business, which was similar to his experience, as he was working on his own craft.

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Jordan and Oakley in Wizards

Eventually they started getting closer and closer and started hanging out together, post which Jordan took Oakley to All-Star in Dallas and took him on his wings, and since then, they’ve always been tight [close].

Oakley also highlighted that getting a foreword in his book from Michael Jordan was nothing short of winning a Grammy or an Emmy, to which Draymond agreed.

Oakley talks about his experience playing against Michael Jordan for the New York Knicks

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Charles Oakley in New York Knicks

Draymond then went on to ask Oakley, what it felt like to play against Michael Jorden, especially after they had such a tight bond while being together in the Chicago Bulls, and keeping in mind the enforcing kind of playing style Oakley had, what did it feel like to get on court with Michael Jordan standing against him.

Oakley laughed and said that when he got traded to the New York Knicks, his job remained the same no matter who he played against, or what team came in front of theirs. He highlighted his task was constant, to clog the middle area no matter who came in front, and let them know that they couldn’t come down the lane because he was still there.

He then went on to say that when he played against Jordan, they both didn’t have any problems with each other, and Jordan took it as business just like he did, and they both went to war with that mentality.

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Charles Oakley

The twist came in when Oakley said that whenever they played against the Bulls, he didn’t see Jordan that much because he played a lot of jump shots, while his game was still the same, and he said the Michael knew that if anyone of the opposite colour came in Knicks’ paint area, Oakley’s job was to step up, which Mike saw when they both practiced together.

Oakley and Jordan struggling to get the ball

Oakley stated that he was the anchor in the Knicks’ defense and they had a pretty good defense, following which he said, “Michael went to the jump shot when I got traded”, and then Oakley said, “he knew he had to pull up, he knew he had to pull up”. Oakley also followed it up by saying that Jordan talked a lot of trash saying “I was born in the wrong time” and further said “hey, he knew if he came down that lane, he’s gonna have to pay a toll”

This conversation between Green and Oakley gave a lot of insights on what it was like playing in a generation full of legends, and specially pointing out the experiences of playing with and against Jordan, which he shall always Cherish.

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