The 2009–10 Toronto Raptors season was the 15th season of the Canadian franchise in the National Basketball Association (NBA). The Raptors were the busiest team in preseason transactions, replacing the previous season's entire roster with the exception of Chris Bosh, Andrea Bargnani, José Calderón, Patrick O'Bryant and Marcus Banks. Although the Raptors were chasing the fourth playoff seed at one point, they capitulated after the All-Star break, and eventually lost the eighth and final playoff spot to Chicago. After the season, Bosh left for the Miami Heat.

The Raptors entered the 2009–10 NBA season in a state of flux: they had failed to qualify for the 2009 NBA Playoffs; it was Jay Triano's first full season in charge; and there was much uncertainty over the futures of perennial All-Star and captain Chris Bosh (who was into the final year of his contract), as well as Shawn Marion and Anthony Parker, both of whom could possibly become free agents before the season began. The roster shakeup began on 9 June 2009, when three-point specialist Jason Kapono ended his two-year tenure with the Raptors, and was traded to the Philadelphia 76ers for the aggressive veteran forward Reggie Evans. Toronto then drafted DeMar DeRozan with the ninth pick, enabling them to fill a spot on the wings. The other major roster change came in the form of signing free agent Hedo Türkoğlu; this led to a sign-and-trade agreement involving four teams, with Toronto landing Devean George (who was later traded for Marco Belinelli) and Antoine Wright, while trading Marion, Kris Humphries and Nathan Jawai. Around the same time, Parker signed with the Cleveland Cavaliers, while Indiana point guard Jarrett Jack was signed to back up José Calderón and former Raptor Radoslav Nesterović was brought back to the fold. Finally, Carlos Delfino and Roko Ukić were moved to the Milwaukee Bucks for Amir Johnson and Sonny Weems. It became increasingly clear that Colangelo, in securing a credible nucleus for the future, was doing this to persuade Bosh to stay.

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