9. Michael Stewart
The original gamble on Stewart was worthy. He went undrafted in 1997 after four years at Cal. The 6’10 big man was an elite shot-blocker in college, and he had a strong rookie season with the Sacramento Kings before becoming a free agent. The Raptors were coming off a 16-win season in 1998 when they signed Stewart to a one-year $1 million contract.
The 23-year-old barely played, but Toronto won seven more games. They believed in his talent and rewarded him with a six-year deal worth $24 million. The Raptors hoped Stewart would blossom into a key piece of their first playoff team, but the contract turned into an absolute disaster.
The 6’10 forward never played more than 24 games in a season and his 9.4 minutes per game in his first season in Toronto turned out to be his best. He never scored more than 2.0 points each night before he was traded to the Cavaliers in a six-player deal in 2003.
Michael Stewart was on the roster for the Toronto Raptors’ first three playoff appearances but only played a total of 14 postseason minutes in his career. The franchise took a shot on a young talent, and it did not pan out. Toronto regretted it as they agreed to pay $25 million for 174 points and 999 total minutes over four seasons.