4 Charles Oakley:
Charles Oakley is remembered primarily as a member of the New York Knicks in the 1990s – the infamous squad featuring Patrick Ewing and John Starks that beat on Michael Jordan and everyone else in the league.
When he joined the Raptors in 1998-99, he brought the same toughness and winning attitude to a team that desperately needed it. Oakley was instrumental in mentoring hall-of-famer Tracy McGrady and future hall-of-famer Vince Carter during their time in Toronto.
Oakley was a veteran presence and enforcer for the young team, but he was more than that.
During the 2000-01 season, Oakley averaged 9.6 points and 9.5 rebounds per game, with 25 double-doubles. He did all of this in his age 37 season.
Oakley then helped the team advance past the first round of the playoffs for the first time in franchise history, and take the Allen Iverson led Philadelphia 76ers to game 7 in the Eastern Conference semi-finals.
Oakley was acquired for the hefty price of a young Marcus Camby, but that shouldn’t factor into his overall ranking with the team.
Charles Oakley was only a Raptor for 3 seasons but he is undoubtedly one of the most influential figures in the franchise’s history.