A classic blue-collar player and one of the premier rebounders in the NBA, Charles Oakley began his NBA career after being drafted by the Cleveland Cavaliers but was immediately traded to the Chicago Bulls in 1985. Traded to the New York Knicks in 1988, he was named to his first All-Star Game in his ninth season, the hardworking 6-9 forward was the heart and soul of a New York Knicks team that reached the 1994 NBA Finals, when his solid defense, rebounding and inside presence provided a valuable complement to the all-around play of All-Star center Patrick Ewing.
On June 25, 1998, after a decade in New York, Oakley was obtained by Toronto along with the rights to Sean Marks and cash for Marcus Camby. He started all 50 games in his first season with the Raptors, providing a veteran presence for a young team striving to become a playoff contender. After helping Toronto get one shot away from the Eastern Conference Finals, Oakley was sent back to the first NBA team he suited up for in a trade with the Bulls on July 19, 2001. After one season in Chicago, Oakley reunited with former Chicago Bull teammate Michael Jordan by signing as a free agent with the Washington Wizards on October 12, 2002.