2. Dwyane Wade (2016)
Contract: 2 years, $47 million
For some members of the fan base, even the mere mention of Dwyane Wade‘s name will be met with a sneer. Wade holds a Voldemort-esque presence in Bulls-related discussions in large part due to the work he put in to sabotage the very team he played for, in the very city he grew up. Instead of following in the footsteps of Derrick Rose to assume the mantle as the next Kid From Chicago, he’d soon be dismissed as He Who Must Not Be Named.
Wade originally signed with the Bulls back in the summer of 2016, inking a massive two-year, $47 million contract with Chicago. It was seen as an overpay at the time, and that much has only become more obvious as time has passed.
In fact, the Bulls offered so much money that the Miami Heat were willing to let Wade walk without a fight. For the first time in his career, Wade would step out on the court in a different jersey than his iconic Miami black and red. The 35-year-old veteran would average 18.3 points and 3.8 assists per game with the Bulls, the lowest mark for him in each category since his rookie season.
To make matters worse, Wade repeatedly provoked the young core of the Bulls in practice and antagonized Jimmy Butler to side against his own team. Rajon Rondo — the third member of the ‘Three Alphas’ — would side with Bobby Portis and the Bulls’ youth in what became a highly-publicized feud in the Bulls’ locker room.
When Rondo went down in the playoffs after beating the first-seeded Boston twice, Wade and Butler looked listless and were swept in the next four games. Wade no doubt played a big role in Butler’s impending departure from the team that year and was subsequently bought out after just one season with the team. Although Wade only spent one season in his hometown, he has no doubt been the biggest backfire signing of a high-profile player in Chicago’s history.