J.B. Bickerstaff (Detroit Pistons)
J.B. Bickerstaff is the most recent head coach on this list, having been the coach of the Cavaliers for the last five seasons. Bickerstaff started his career as an assistant coach with the Charlotte Bobcats in 2004, with additional stints with the Timberwolves, Rockets, and Grizzlies before joining the Cavs and moving up the ranks. The Pistons' job will come with a lot of early struggles, with Bickerstaff being their third coach in three seasons and the first move by the new regime spearheaded by Trajan Langdon, President of Basketball Operations. Detroit was one of the worst teams in the league last season, losing 28 consecutive games (tied for the longest streak in NBA history). There are many promising young players in Detroit, including Cade Cunningham, Jalen Duren, Ausar Thompson, and their fifth overall draft pick, Ron Holland. Bickerstaff has worked with young players before, including Darius Garland and Evan Mobley, and will need to develop the Pistons' talent the right way to help restore the franchise to its former glory. His all-time coaching record is 255-290, but over his five-year stint with the Cavaliers, he had a winning record of 170-159, with 99 wins over the last two seasons. He also has the most recent head coaching playoff success out of any of the new hires, leading the Cavaliers to a second-round exit in five games to the Celtics.