He has also been an assistant for the Portland Trail Blazers,[3] Chicago Bulls,[4] Los Angeles Lakers, and Cavaliers.

[citation needed] He attended East Benham High School, where he was the starting point guard of the basketball team.

[citation needed] After graduating in 1961, Bickerstaff moved to Cleveland where he had relatives, with the idea of joining the Army, but he instead accepted a basketball scholarship to play for Rio Grande College.

The racial tension he experienced during his time playing there made him leave school early and head back to Cleveland to work in a steel mill.

As a senior, he was named team captain and MVP, when the Toreros finished 17–11 and went on to play at the Small College Regional Playoffs.

After finishing his college eligibility, Bickerstaff was hired by his coach Phil Woolpert to serve as an assistant for the 1968–69 season.

[5] In 2003, Bickerstaff was hired by Ed Tapscott to become the expansion Charlotte Bobcats' first head coach and general manager.