Tex Winter
Winter served as an assistant coach to the Chicago Bulls from the 1985-86 season through the 1998-99 season, during which time the team won six NBA championships.  Most of this time was spent working with head coach Phil Jackson, starting from the 1987-88 season.  He also went with Jackson to the Los Angeles Lakers for five seasons, from 1999 to 2004, winning another three NBA championships.