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Charles Oakley is a journeyman power forward in the National Basketball Association. He has been a significant contributor to playoff teams in Chicago, New York, and Toronto, over the course of a 17-year career.

Charles Oakley was born in Cleveland, Ohio, on December 18th, 1963. He played for John Hay HS in Cleveland, then went on to Virginia Union, a Division ii school. Very few NBA players ever come out of Division ii, and even fewer have successful, long-term careers such as Oakley's.

Oakley was a star at Virginia Union, starting as a freshman, averaging a double-double in points and rebounds in each of his four seasons, and leading all Division ii players in rebounding (17.3 rpg), in his senior year.

Oakley's hometown Cleveland Cavaliers made him the 9th pick in the 1985 NBA Draft. Oakley was drafted ahead of such players as Karl Malone and Joe Dumars. He never played a single game for the Cavs, as he was traded to the Chicago Bulls for Ennis Whatley and Keith Lee. It was a very one-sided deal for the Bulls. The Bulls got a tough as nails young power forward to play along side Michael Jordan. The Cavs got years of mediocrity from Whatley and Lee.

Oakley's rookie season was a success. In 23 minutes of playing time per game, he averaged close to 10 points and 9 rebounds. As a starter, in his second season, he averaged 14.5 points and 13.1 rebounds, both career highs. Oakley led the league in total rebounds in 1987 and 1988, having over 1,000 rebounds in both seasons. However, the Bulls did not enjoy much playoff success, and in the 1988 draft, selected a pair of young forwards, Horace Grant and Scottie Pippen, whose presence made "The Oak Man" expendable. He was traded to the New York Knicks for veteran center Bill Cartwright.

Oakley spent nine years in New York, and became a fan favorite for his tough defense and hustle. It was a common sight to see Oakley diving into the front row of seats for a loose ball, with the cameramen and Spike Lee scrambling out of his way. Oakley set the tone for a Knicks team, under coach Pat Riley, that introduced the concept of low-scoring games with thuggish defense. Riley's defensive philosophy can be summarized as "Foul them until the refs get tired of blowing their whistles." Oakley made his lone All-Star appearance as a Knick in 1994, when he averaged late-career highs of 12 points and 12 rebounds, and the Knicks made it all the way to the NBA Finals, losing a heartbreaking 7-game series to Hakeem Olajuwon's Houston Rockets. Oakley was also a vocal team leader, and was instrumental in the development of younger players such as Anthony Mason.

The Toronto Raptors thought they were getting this tough player and positive clubhouse influence when they dealt for Oakley, but they were mistaken. Oakley's physical skills had begun to deteriorate noticeably in the 1998 season, when he was forced to play center due to a serious injury to Knicks' superstar Patrick Ewing. The Raptors dealt promising young forward Marcus Camby to the Knicks, and what they got in return was a belligerent and divisive player whose three years in Toronto were marked by a field-goal percentage that dropped faster than the Nasdaq, who publicly blasted his teammates and coaches, and who was suspended for punching Jeff McInnis of the Los Angeles Clippers during a morning shootaround, apparently in a dispute over a woman. The Raptors grew tired of Oakley's act and shipped him back to the Chicago Bulls, now a perennial basement-dweller, for a little-used forward named Brian Skinner. Oakley's half-season in Chicago has been more of the same. Oakley has made constant demands to be traded to a contender, and publicly ridiculed both the front office and since-fired coach Tim "Pink" Floyd. Ironically, the man who replaced Floyd as the Bulls' coach was Bill Cartwright, who had once been traded for the Oak Man.

As a player, Oakley's game is primarily a defensive one. He spent nine years in New York as Patrick Ewing's caddy, guarding the other team's best player. Despite only standing 6 foot 9 and weighing 245, Oakley can guard much larger players. He is a very tough rebounder with excellent fundamental skills, averaging 9.5 rebounds last year at the age of 38. He was never a very good offensive player, nor did he possess incredible physical ability. His major offensive weapon is his jump shot, which has deserted him almost entirely. He scores on garbage points, and has no post moves to speak of. He does have better-than-average passing skills for a big man, but unfortunately the impression Oakley is leaving on the league is that of an aging player who has anger-management issues, and is quickly wearing out his welcome.

Oakley is also a successful entrepreneur who owns a string of car washes, mostly in the Cleveland area.

Update (2/25/03): Charles Oakley signed a contract with the Washington Wizards for the 2003 season. He rarely plays, but has been effective in short bursts. On the Wizards, Oak was re-united with former teammates Michael Jordan and Patrick Ewing, now an assistant coach for the Wiz.

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