Chicago Bulls (1985–1988) 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, alongside
Calvin Duncan, for
Ennis Whatley and
Keith Lee. Oakley provided another scoring option and steady offensive and defensive performances to an up-and-coming Bulls squad led by
Michael Jordan. On March 15, 1986, Oakley set a career high in points scored with 35, during a 125–116 loss to the
Milwaukee Bucks. Oakley was selected as a part of the
NBA All-Rookie First Team in
1986. Oakley also assumed the role of the team "enforcer", whose duty primarily was to protect young Jordan against cheap shots and roughhousing tactics of opposing players. He was given the nickname, "Oak Tree", for his rugged demeanor and no-nonsense attitude. On April 26, 1987, Oakley set a postseason career high with 25 points scored, alongside grabbing 15 rebounds, in a loss to the
Boston Celtics. At the end of the 1987-88 season, Oakley and
Michael Cage, then of the
Los Angeles Clippers, were in close competition to be the season's top rebounder. In the penultimate game of the season for the Bulls, Oakley collected 35 rebounds in a loss against the
Cleveland Cavaliers, which remains the most in a single game since
1979. Two nights later, Oakley had 21 rebounds against the
Boston Celtics to close the season. When Cage arrived at the Clippers' game later on, a note with the number 28 (the number of rebounds he would need to overcome Oakley) was taped to his locker. Cage would play all 48 minutes in that game and collect 30 rebounds.
New York Knicks (1988–1998) 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,
Anthony Mason 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. On June 1, 1994, Oakley scored 12 points, grabbed 13 rebounds and recorded 7 assists in a Game 5 loss to the
Indiana Pacers in the Eastern Conference Finals. The Knicks eventually won that series. The following round, during that year's
NBA Finals, Oakley averaged 11 points and 11.9 rebounds per game in a tightly contested seven-game series loss to the
Houston Rockets. On March 11, 1998, Oakley grabbed a season high 22 rebounds in a loss against former teammate
Anthony Mason and the
Charlotte Hornets. Despite regular season success and consistent playoffs appearances, the Knicks did not return to the Finals again during Oakley's tenure. During his time with the Knicks, Oakley was known across the league for being a defensive specialist and outstanding rebounder.
Toronto Raptors (1998–2001) In 1998, Oakley was traded by New York to the
Toronto Raptors, alongside
Sean Marks, for blossoming star
Marcus Camby. For the Raptors, he provided a veteran presence to a young team that included
Vince Carter and
Tracy McGrady. On January 7, 2001, Oakley set a career high with 6 blocks, and also narrowly missed a
triple-double with 12 points, 10 rebounds, and 7 assists.
Return to Chicago (2001–2002) In 2001, Oakley was traded by the
Toronto Raptors with a 2002 2nd-round pick to the
Chicago Bulls for
Brian Skinner. This was his second tenure with the Bulls. Starting 36 of his 57 played games, he averaged 3.8 points per game, 6 rebounds per game, and 2 assists per game.
Washington Wizards (2002–2003) In 2002, Oakley signed as a free agent with the
Washington Wizards, where he was reunited with former teammate
Michael Jordan. Oakley played 42 games during the
2002–03 season, averaging 1.8 points per game, 2.5 rebounds per game, and 1 assist per game. ==Coaching and businesses==