Born and raised in Cleveland, Oakley attended John Hay High School and Virginia Union University, a Division II historically black university in Richmond, Virginia. As a senior in 1984–85, Oakley led Division II in rebounding with an average 17.3 per game.\n', '

Oakley was drafted with the 9th overall pick in the 1985 NBA draft by the Cleveland Cavaliers, but his draft rights were traded to the Chicago Bulls. Oakley provided another scoring option and steady offensive and defensive performances to an up-and-coming Bulls squad led by Michael Jordan. He also assumed the role of the team "cop" whose duty primarily was to protect young Jordan against cheap shots and roughhousing tactics of opposing players. Oakley earned All-Rookie Team honors in 1986.\n', '

With the drafting and development of Horace Grant, the Bulls traded Oakley to the New York Knicks for 7\'1" center Bill Cartwright. Oakley eventually became a part of the core which the Knicks built around, which also featured Patrick Ewing, John Starks, and point guard Mark Jackson. During the Knicks\' 1994 season, which included a record 25 playoff games, Oakley started every regular season and playoff game for a record 107 starts in a single season. During his tenure with the Knicks, Oakley was primarily known as a defensive specialist.\n', '

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