If Cavaliers brass values experience, Terry Stotts should be at the top of the list of potential hires. Stotts served as head coach of the Portland Trail Blazers from 2012-21, guiding the team to three 50+ win seasons and eight playoff appearances. Before his time in Portland, the Iowa native was also bench boss of the Atlanta Hawks and Milwaukee Bucks from 2002-04 and 2005-07, respectively. Stotts is 66 years old and has been out of the league for three full seasons, but his previous success cannot be overlooked.