It seems inexplicable that Andrew Bogut’s tenure in Cleveland could rank above anyone else, but at least he didn’t actively contribute to the Cavaliers losing as Anthony Bennett did. Unfortunately, Bogut didn’t contribute much of anything to a Cavs team on its way back to the NBA Finals.
Bogut was drafted first overall out of Utah by the Milwaukee Bucks and established himself as a skilled offensive player who was one of the league’s best defenders. He made a name for himself starting for the Golden State Warriors, winning the title in 2015.
In 2017 he signed with the Cavaliers for the playoff run but broke his leg less than a minute after checking in, ending his Cleveland career before it could begin.
Few players embody a region of the country quite so much as Kent Benson. The 6’11” center grew up in Indiana, won a National Championship during his four seasons at Indiana University, then spent the bulk of his playing career with the Milwaukee Bucks and Detroit Pistons after he was drafted first overall in the 1977 NBA Draft.
Late in his career, Benson ended up with the Cleveland Cavaliers in what would be his final run of play in the NBA. He played in just two games during the 1987-88 season, scoring five points in 12 total minutes (he didn’t miss a shot! 2-for-2). He would play a single season in Italy before calling it quits on his basketball career.