10. Rafer Alston
Alston is a New York City legend that spent many days dominating at Rucker Park. The 6’2 guard made the transition from streetball to the NBA, but it was a slow start. He spent his first three years in Milwaukee but never played more than 13.4 minutes per game. After a brief stint with the Warriors where he never appeared in a game, Alston signed a rest-of-season contract with the Raptors in 2002.
He was the team’s backup point guard for 47 games, and it opened more opportunities. Alston was in his prime and signed with the Miami Heat in 2003 where he averaged over 21 minutes per game for the first time and proved he could be a key rotation piece. The following offseason, the Raptors needed a point guard, so they inked Alston to a six-year contract worth $29 million.
His second stay only lasted one season. The Raptors won seven more games than the previous year, but they still missed the playoffs. Alston had arguably the best statistical year of his career as he started 78 of his 80 games played and averaged 14.2 points, 6.4 assists, and 1.5 steals in 34.0 minutes per game, but there were behind-the-scenes issues that prompted his short stay.
Rafer Alston was traded for Mike James in October 2005. James lasted just one season in Toronto, but he too had arguably the best year of his career with the Raptors. It was disappointing to see the streetball legend exit so quickly after signing a massive contract, and Toronto likely regretted the deal.