Carter was initially drafted by the Golden State Warriors with the fifth overall pick in the 1998 NBA draft. He was then traded to the Toronto Raptors for the fourth overall pick, Antawn Jamison, Carter's college teammate and friend. The Raptors had struggled in their first three years as a franchise. Carter was instrumental in leading the Raptors to their first-ever playoff appearance in 2000 before going on to lead them to a 47-win season and their first-ever playoff series win in 2001, advancing them to the Eastern Conference Semifinals.