2. Michael Stewart
The fact that Stewart is not often mentioned among the worst free agent signings in NBA history is baffling, as the Raptors got almost nothing of value from him. After blocking 2.4 shots per game in his rookie season with the Kings, the Raptors signed him to a whopping six-year contract worth $24 million in 1999.
Stewart proceeded to show he was not an NBA player beyond that magical stretch with Sacramento. Averaging 1.4 points per game for that money is bad enough, but doing so while also playing 121 games for the franchise shows how desperate the team was to justify the contract.
Michael Stewart struggled for the Toronto Raptors.
Stewart somehow convinced three other teams to take a chance on him, but neither the Cavaliers, Celtics, or Hawks could get Stewart back to his Kings days. His career fizzled out after that, with his most prominent achievements coming during his first season.
Masai Ujiri might get some heat for keeping the team together too long, but at least he is holding on to remnants of a championship team. Stewart’s tenure with the Raptors was one of ineffectiveness and disappointment, etching him a place in the more infamous corners of the franchise history books.