Skip to main content

Rob Dillingham has chance to elevate entire Caleb Wilson Bulls era

If Rob Dillingham develops this season, he could help elevate the Caleb Wilson Chicago Bulls era.
Mar 27, 2026; Oklahoma City, Oklahoma, USA; Oklahoma City Thunder guard Jalen Williams (8) passes around Chicago Bulls guard Rob Dillingham (7) during the second half at Paycom Center. Mandatory Credit: Alonzo Adams-Imagn Images
Mar 27, 2026; Oklahoma City, Oklahoma, USA; Oklahoma City Thunder guard Jalen Williams (8) passes around Chicago Bulls guard Rob Dillingham (7) during the second half at Paycom Center. Mandatory Credit: Alonzo Adams-Imagn Images | IMAGN IMAGES via Reuters Connect

The Chicago Bulls have a very important season ahead of them, and Caleb Wilson will be the key to it all. But they need some players on the bench to step up and help them, too. One of the more interesting guys on Chicago’s bench next season could be Rob Dillingham, who the Bulls acquired at the trade deadline last year.

Dillingham was a top-10 pick just two seasons ago. A guy who the Minnesota Timberwolves traded up to select. Yet they were very willing to give up on him very early in his career. But now, the Bulls have a chance to give him a second home. That could be what he needs, especially after a full season of getting integrated into things.

If Dillingham can become a legitimate rotational point guard for the Bulls, it could help significantly elevate the future outlook of the Wilson era.

Rob Dillingham development could elevate Caleb Wilson era

In theory, Dillingham should be a very interesting score-first point guard for the Bulls. And that’s the exact type of thing that the Bulls need moving forward. A guy who can help the offense.

During his single season in college at Kentucky, Dillingham showed enough to be a top-10 pick in the draft. A guy the Wolves were willing to take a huge bet on.

Unfortunately for Dillingham, the Wolves are trying to win right now. They are trying to make the most of the Anthony Edwards era, pushing for championships in a stacked Western Conference.

Point guards take a lot of time to develop. And in today’s NBA, situation matters more than ever. So if the Bulls actually give Dillingham some developmental playing time, perhaps he could get back to being the player he was once supposed to be.

Dillingham is a very crafty ball-handler. At his best, he can beat guys off the dribble, get to the rim, and find his jump shots on the outside. Adding that type of player – especially a dynamic one like Dillingham is supposed to be – would really help.

Wilson is the star of the show. Or at least, he’s supposed to be. That’s who the Bulls drafted him to be. An elite 3-and-D star-level talent who can be the face of the franchise in Chicago moving forward.

He needs offense around him. Players who can help lift things up on the offensive end. Dillingham has the potential to be one of those players.

He isn’t right now, but a good season of development could seriously help get them moving in the right direction.

Add us as a preferred source on Google

Loading recommendations... Please wait while we load personalized content recommendations