Since culture changer Masai Ujiri entered as general manager in 2013, the Toronto Raptors have been considered one of the best-run organizations in the league. They haven’t made many missteps during Ujiri’s tenure with the Raptors, and they even won their first NBA Championship in franchise history during the 2018-19 season. They’ve also made the playoffs nine of the 10 years under the management of Ujiri.
But this is not a franchise that has always been viewed as one of the premier organizations in the NBA. In fact, from when the team first debuted in the NBA during the 1995-96 season up to the 2013-14 season, the Raptors only had one playoff series win in their history.
On top of the lack of playoff success, the Raptors have had more than a few missteps when it comes to personnel. Looking back, we explore and rank the seven worst free agent signings in team history.
Ranking the seven-worst free-agent signings in Toronto Raptors franchise history.
7. Michael Stewart
The contract: Six years, $24 million (1998, 1999)
After a solid rookie season, the Toronto Raptors were hoping that big man Michael Stewart would continue to develop into a difference-maker. However, that didn’t exactly happen. He would end up becoming one of the team’s worst signings in franchise history.
During his four seasons with the Raptors, Stewart only played in 121 games and didn’t average more than two points per game, nor did he play more than 10 minutes per contest. All in all, it was a pretty bad signing considering how little Stewart played for the Raptors and the length of the deal. At least they realized their mistake quickly and moved off him.