Oakley provided another scoring option and steady offensive and defensive performances to an up-and-coming Bulls squad led by Michael Jordan.

[5] 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.

[6][7] 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.

[8] With the drafting and development of Horace Grant, the Bulls traded Oakley to the New York Knicks for 7'1" center Bill Cartwright.

[9] 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.

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 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.

[13] In 1998, Oakley was traded by New York to the Toronto Raptors, alongside Sean Marks, for blossoming star Marcus Camby.

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.

[29] On February 8, 2017, Oakley was involved in an altercation at Madison Square Garden as the Knicks faced the visiting Los Angeles Clippers.

In a statement, the Knicks stated that Oakley "came to the game tonight and behaved in a highly inappropriate and completely abusive manner.

"[31] In response, Oakley claimed that he sat down in his seat and he saw the Knicks owner James Dolan look at him and within four minutes he was being asked to leave the arena.

[32] While admitting "I shouldn't have put my hands on anyone," Oakley disputed the Knicks' rendition of events in an interview with ESPN's The Undefeated, which reported that Oakley says he "never said a word to Dolan" and "was minding his own business when he was confronted by Madison Square Garden Security, who asked why he was sitting so close to Dolan before demanding that he leave the building.

[36] Oakley later retorted on March 11, 2019, that Dolan is someone who tries to bully everyone because he has money and power as an owner of the Knicks, quoting that "it doesn't make sense.