8. Wesley Matthews
Matthews signed a minimum deal with the Bucks in 2019 to help replace Malcolm Brogdon. The 6’4 wing rarely missed a game and had started for virtually his entire career. He beat out Donte DiVincenzo and Pat Connaughton for the starting gig, but the 33-year-old was past his prime. Matthews was best suited for 20-25 minutes per game and not the 30-plus he played for nearly a decade straight.
Matthew tore his Achilles in 2015 and his shooting efficiency never returned. The 6’4 guard made 39.6 percent of his field goals during his lone season as the Bucks’ primary starter. He averaged 7.4 points and 2.5 rebounds in 24.4 minutes per game. Matthews played stout defense and sunk threes, but his questionable shot selection and age caught up to him. The Bucks reached the second round of the playoffs before being bounced by the Miami Heat inside the bubble.
Matthews left to join the Lakers in the 2020 offseason before returning to Milwaukee one year later for two more seasons. The 6’4 guard was reserve in his second stint, and it was clear that he was overplayed in his first season with the Bucks.
The 14-year NBA veteran is still searching for his first championship. He moved on from the Bucks in the 2023 offseason. Matthews shooting under 40 percent from the field and not playing 30-plus minutes earns him a place on this list.