Oakley was born in Cleveland, Ohio, and attended Virginia Union University.
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. Oakley provided another scoring option and steady offensive and defensive performances to an up-and-coming Bulls squad led by Michael Jordan. Oakley earned All-Rookie Team honors in 1986.
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, 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 and top NBA rebounder.
Toronto Raptors (1998-2001)
In 1998, Oakley was traded by New York to the Toronto Raptors for blossoming star Marcus Camby. For the Raptors, he provided a veteran presence to a young team that included Vince Carter and Tracy McGrady.
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. He was reunited with former teammate Michael Jordan. Oakley played 42 games during the 2002-03 season.
Houston Rockets (2004)
The 2003-04 season was Oakley’s last. On March 18, 2004, Oakley signed the first of two 10-day contracts with the Houston Rockets. Oakley only played 7 games and at the end of the season, Oakley retired from the NBA.
• He placed in the Top 10 in rebounds per game average five times between 1987 and 1994. In all but one of these seasons he played the full complement of 82 games.
• He placed in the Top 10 in total rebounds 6 times and led the league in total rebounds twice (1987 and 1988).
• In 1994, he became an NBA All-Star and was chosen to the league’s All-Defense 1st team.