6. DeMarre Carroll
Signing Carroll was a rare miss by Masai Ujiri. The 6’6 wing helped the Hawks reach the conference finals in 2015 and entered free agency at the near-perfect time. The salary cap was rapidly climbing, and Toronto was eager to improve after back-to-back first-round playoff exits. It resulted in a four-year $60 million contract that quickly became one of the worst signings in franchise history.
Carroll struggled to hit shots, but his counting stats were strong in his first year with Toronto. He suffered multiple injuries, which limited him to just 26 games. The 6’6 wing returned for the playoffs and helped the Raptors reach the conference finals, but his production dipped as he shot 39.0 percent from the field in the postseason.
Things got worse in year two as his 3-point percentage dipped below league average for the first time in four years. His tenure turned into a disaster, and the Raptors traded him with two first-round picks to the Nets in the 2017 offseason.
To make matters worse, DeMarre Carroll bounced back in Brooklyn and helped the Nets return to the playoffs in 2019, which was the precursor to getting Kevin Durant and Kyrie Irving in free agency. The Toronto Raptors would love a do-over on the Carroll signing, but he was not the worst starter of the Kyle Lowry era.