Rob Dillingham is entering a make-or-break third season in the league. After his tenure with the Timberwolves didn't go as planned, the former eighth-overall pick was traded to the Bulls at the deadline. He got an opportunity in Chicago down the stretch of last season, but wasn't particularly effective. Now, he is facing an uphill battle for a role next season. The Chicago Bulls revamped their roster this summer under new GM Bryson Graham and head coach Tiago Splitter, building an exciting team with a lot of young players with upside. Chicago's deep roster will squeeze some of the players lower on the totem pole, and one of those players is the 21-year-old guard Rob Dillingham. The Bulls selected Dailyn Swain with the 15th-overall pick, and on paper, Swain is a shooting guard/small forward-sized player. However, the Bulls may be thinking of him more as a ballhandler and playmaker. Swain said that he will be on the ball quite a bit in Summer League and beyond, which puts Dillingham in a difficult position. Josh Giddey is the surefire starter at point, and Tre Jones is an established backup point guard who has proven himself more than Dillingham on both ends of the floor. As long as Giddey and Jones are both healthy, there is little room for Dillingham in the backcourt. Dillingham can play next to another point guard as an off-ball threat, but he needs to get significantly better defensively for that to be sustainable. As an undersized guard who has been a defensive liability so far in his career, his fit with another point guard like Giddey and Jones is highly questionable. There will be plenty of injuries during the long NBA season, and Dillingham will get his chances. Unless he makes the most of them right away to start the season, it's difficult to see him rise in the depth chart. The Bulls are more focused on the future than the present, and there is no reason why they wouldn't allow the rookie Swain to explore his role. This puts pressure on Dillingham to perform and prove himself as a valuable asset to the team. With the new era of Bulls basketball underway, Dillingham's future with the team is uncertain, and he will have to work hard to secure a spot in the rotation.