9. Jason Caffey
Landing in Milwaukee in the final seasons of his career, Caffey never fully managed to live up to some of the flashes of potential he displayed in his early years with the Chicago Bulls, in spite of the two championship rings he has to show for his time in the Windy City.
Still, Caffey became a meaningful contributor for the Bucks during the time of their resurgence at the turn of the millennium, and could have continued beyond that if issues with anxiety and other off the court distractions hadn’t gotten in the way.
The Alabama native arrived for his first year with the team as they worked their way towards the Eastern Conference Finals and played a meaningful role providing energy off the bench for that group.
Caffey would remain in Milwaukee for two seasons beyond that and for his three seasons overall as a Buck, he averaged 6.2 points and 4.0 rebounds, while shooting 47.7 percent from the field across 144 games.