Not long removed from winning their division and making the playoffs, the Raptors were once again back in the lottery, the reigning coach of the year fired, and the thought of rebuilding (again) seemed imminent.
The experiment known as Jermaine O'Neal failed as he was traded for forward Shaun Marion.
General Manager Bryan Colangelo had to find some way to satisfy his All-Star big man and Olympic gold medalist Chris Bosh.
Bosh had to come into the season optimistic, after not only playing for the coach of the year, winning the Atlantic division, and a gold medal, things were finally looking up. Or so he thought.
Too bad for Bosh, he was quickly brought back to the harsh reality that the Raptors seem to be stuck in.
Entering the 2009 offseason, Colangelo had a plan. First to bring back Marion and Anthony Parker and build around the nucleus of Marion, Parker, and Bosh with young solid talent.
He drafted DeMar Rozan, the insanely athletic guard from USC. He reminds many of a young Vince Carter.
However, that plan was quickly set ablaze less than 24 hours after signing break-out star Hedo Turkoglu. Parker had reached a deal with the Cleveland Cavaliers.
Colangelo had to make a move, quickly, or else risk the happiness of his star and lose all hope of resigning him in 2010.
Jarrett Jack signed not long after Turkoglu, reuniting Bosh with his college teammate. He also signed big man, Rasho Nesterovic to a two-year deal.
He also traded Marion to Dallas for athletic guards Antoine Wright and Devon George, as well as adding toughness to his front court by trading sharpshooting Jason Kapono for energetic big man Reggie Evans.
Not long after trading for George however, he was traded for Golden State swingman Marco Belinelli. He also traded Carlos Delfino for the young and athletic Amir Johnson from the Milwaukee Bucks.
Colangelo completely retooled the Raptors rosters, as well as naming Jay Triano head coach.
Led now by Bosh, Turkoglu, and their explosive point guard Jose Calderon, the Raptors now have the tools to compete as one of the top teams in the Eastern Conference.
Bosh has made it clear that underachievement is not an option. Colangelo has provided his response and built a team that can now play up to if not better than Bosh's standards.