Rob Dillingham’s 84 regular-season and three postseason outings with the Minnesota Timberwolves didn’t quite go as expected. Selected eighth overall in the 2024 NBA Draft, Dillingham was acquired by the Wolves after they made a draft-day deal with the San Antonio Spurs for that pick.
At the 2026 trade deadline, Dillingham was traded to the Chicago Bulls in the deal that brought Ayo Dosunmu to Minnesota.
The 21-year-old didn’t get to face his former club after joining Chicago, but his first chance to do so will come in the preseason on October 16.
Dillingham’s preseason could determine how many minutes he gets for Chicago to begin the regular season
The Timberwolves have more preseason games than most teams, with six on the docket. Their final one comes on the road against the Bulls.
The expectation is that the Timberwolves will get to see a good amount of their former lottery pick. Chicago played Dillingham substantially more last season than Minnesota ever did. However, that came while the Bulls were mostly out of contention.
It will be important for Dillingham to show out in the preseason if he wants to have a large role again. The Bulls have backcourt players who could be ahead of him in the pecking order, including Josh Giddey, Tre Jones, and Norman Powell. Wings Isaac Okoro and rookie Dailyn Swain could also get minutes in the backcourt.
Wolves fans should tune in—even if they don’t normally watch the preseason—to see how Dillingham performs. They shouldn’t be rooting against him, but it’s always a risk to get rid of someone who was once thought so highly of so early in his career. Dillingham was a sharpshooter during his one year of college basketball at Kentucky, but that ability hasn’t translated yet during his two years in the NBA.
Even if Dillingham does show improvement, the Timberwolves still got Dosunmu in exchange for him. In Dosunmu’s brief time with Minnesota, he showcased the ability to be a knockdown shooter and take the ball to the basket. The Wolves rewarded him with a new five-year contract this offseason.
Not only is Dillingham in Chicago, but Timberwolves fans can also watch the game to see Leonard Miller, who was also involved in that trade. He also saw plenty more playing time after leaving Minnesota. No, they didn’t work out for the Wolves, but they have a better chance to develop with more playing time on a Bulls team with lower expectations.
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