Charles Oakley (born December 18, 1963) is an American former professional basketball player. Oakley is best known for playing ten of his nineteen seasons in the National Basketball Association with the New York Knicks. As a power forward, he consistently ranked as one of the best rebounders and defensive players in the NBA. He also played for the Chicago Bulls, Toronto Raptors, Washington Wizards, and Houston Rockets. From 2017-2025, he was the coach of the Killer 3's of the BIG3.

Charles Oakley was born December 18, 1963, in Cleveland, Ohio, where he was raised. Oakley attended John Hay High School, where he excelled in basketball.^{[citation needed]}

Oakley attended Virginia Union University, a Division II historically black university in Richmond, Virginia. As a senior in 1984–85, Oakley led Virginia Union to the 1985 NCAA championship. The Panthers had a 31–1 overall record that year, with Oakley averaging 24 points and 17.3 rebounds a game. Oakley was named the NCAA Division II Player of the Year. He scored 2,379 points and grabbed 1,642 rebounds in his college career.

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.

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.