Acquired from the Timberwolves at the trade deadline, Dillingham struggled with a right wrist injury early in his arrival in the Windy City. However, the second-year guard made strides down the stretch, shooting just over 46 percent from the field in April. With Josh Giddey under contract for the next three seasons, Dillingham’s best opportunity at playing time in 2026-27 is likely to be as the backup point guard if he can win the job in training camp.