6. Matthew Dellavedova
Dellavedova helped LeBron James and the Cavaliers win the championship in 2016, and his all-out style caught the eye of then-Bucks head coach Jason Kidd. Milwaukee signed the 26-year-old to a four-year $38 million contract in 2016. The Bucks were searching for a capable point guard who would not dominate the ball.
Dellavedova started just 31 games over his first three years in Cleveland, but the Bucks opened the season with the 6’3 guard in that role.
He opened 54 of his 76 games played in the 2016-17 season but left plenty to be desired. Delly averaged 7.6 points, 4.7 assists, and 1.9 rebounds in 26.1 minutes per game. He shot just 39.0 percent from the field and averaged nearly two turnovers each night. The Bucks brought him off the bench in the playoffs, and it was clear that Dellavedova was overmatched as a starter.
He played just 38 games the following season and his minutes and production dropped off when healthy. Delly could not find his shot, and Milwaukee needed to move.
The Bucks traded him back to Cleveland in Dec. 2018 for George Hill. Matthew Dellavedova was a capable backup, but not a starting point guard in the NBA. Milwaukee made a massive mistake in giving him over $9 million per season, and Delly earned his place on this list.