He was as strong as a tree, an oak. Oakley was a rebounder, defender and intimidator who also had a soft touch on his outside shot.
At Virginia Union University, Charles Oakley was a machine on the glass. For his four years of college his average was 14 rebounds per game. For his senior season he was at 17.3 rebounds per game. He did also score with around 20 points at 60% from the field.
The Cleveland Cavaliers have made some good picks and bad trades over the years, especially in the 1980s, and drafting Oakley for Chicago didn’t help them a lot.
Cleveland used pick 9 of the 1985 draft to get Oakley. The trade that was made was Oakley and Calvin Duncan going to the Chicago Bulls for Keith Lee and Ennis Whatley. A big win for Chicago.
In his first season with the Bulls, they gave him 23 minutes a game and Oakley brought down 8.6 rebounds per game. It didn’t take long for Chicago to figure out they had a star, he played all 82 games in his second season of NBA basketball and started in 81 of them.
During that second season, 1986-87, Oakley averaged 14.5 points and 13.1 rebounds. He also had 3.6 assists per game, a very good number for a power forward.
Chicago was good with Oakley, but they also had Horace Grant and wanted a center with height. In New York, they had a center who needed a strong power forward next to him, and another center they were willing to trade.
A deal was made, Oakley was sent out by the Chicago Bulls with a 1988 first round draft pick and a 1988 third round draft pick to New York for Bill Cartwright, a 1988 first round draft pick and a 1988 third round draft pick. The teams moved around the draft but it was mainly about Oakley becoming the power forward for New York and Cartwright becoming the new starting center for Chicago.
Oakley wasn’t part of the Bulls’ titles but he went close with New York. Oakley also played in an All-Star game during his time with the Knicks.
In 1994 Oakley played 11 minutes in the All-Star game, finishing with 2 points, 3 rebounds and 3 assists. Oakley played a long time with New York, hitting outside shots on offense to keep teams from crowding around Ewing while also playing great defense and getting many rebounds.
In June of 1998, there was a chance for New York to get younger and more athletic and they made a trade. It was Oakley and Sean Marks and some cash going to the Toronto Raptors for forward/center Marcus Camby.
Toronto wasn’t getting the best that Camby could provide and they also wanted Oakley for his toughness.
Oakley went back to one of his previous teams, Chicago, for the 2001-02 season. The deal was Oakley and a 2002 second round draft pick to the Chicago Bulls with Brian Skinner going to Toronto. Oakley would only play one season with Chicago.
Oakley signed as a free agent with the Washington Wizards in October of 2002. He was back in the role of Michael Jordan’s bodyguard.
Both players were far from their prime at that time, Jerry Stackhouse led the team in scoring average ahead of Michael Jordan while Oakley only played 12.2 minutes a game for 2.5 rebounds which was below the numbers that Christian Laettner and Kwame Brown had.
Oakley’s career would end with a small amount of games with the Houston Rockets. They brought him in on a couple of 10-Day contracts late in season 2003-04.