As much as you guys hate him, we all know he is the greatest player to ever wear Raptors across their chest. In 1998, Carter was drafted by the NBA's Golden State Warriors with the fifth overall pick, and then traded to the Toronto Raptors for the fourth overall pick, Antawn Jamison, his college teammate and good friend. Carter's rookie season was the shortened 50-game 1999 season, after the NBA locked out its players in 1998–99. Carter started almost every game for coach Butch Carter, averaged 18.3 points per game (ppg), and eventually won the NBA Rookie of the Year Award.
The next year, Carter was selected to an All-Star Team for the first time, averaged 25.7 ppg, made the Third Team All-NBA, and showcased his athleticism and dunking abilities in the 2000 NBA Slam Dunk Contest. He won the contest by performing an array of dunks including a 360° windmill, a between the legs bounce dunk, and an elbow in the rim dunk (also known as a cookie jar dunk or the honey dip.
In Carter's first two seasons, he and his distant cousin Tracy McGrady formed a formidable one-two punch as Raptor teammates. The two led the Raptors to their first playoff berth in the 2000 NBA Playoffs, but they were swept in the first round by the New York Knicks, in 3 games.
Upon McGrady's departure to the Orlando Magic the following season, Carter became the Raptors' franchise player. In 2000–01, his third season, Carter averaged a career-high 27.6 ppg. while the Raptors finished the regular season with a franchise-record 47 wins. In the playoffs, the Raptors beat the New York Knicks 3–2 in the first round, and advanced to the 2001 Eastern Conference Semifinals, where they took the Philadelphia 76ers to a decisive seventh game. On the morning of the day of Game 7, Carter attended his university graduation. In that game, Carter missed a game-winning shot with 2.0 seconds remaining.
The next season was an injury-riddled one for Carter. He started in 60 games and he averaged 24.7 ppg. He was voted into the 2002 NBA All-Star Game, but he could not participate due to injury. The Raptors did not fare well without their All-Star player. The team lost 17 of 18 games to drop to 30–38, then won 12 of their last 14 to finish at 42–40. Carter was injured during the 2002 NBA Playoffs, and his team was defeated in the first round by the Detroit Pistons, in five games. After a few years of struggle Vince Carter was traded to the New Jersey Nets.