Rob Dillingham is beginning to rediscover his confidence and his game since arriving in Chicago. Acquired by the Chicago Bulls at the trade deadline, the 21-year-old guard has embraced a new offensive environment that contrasts sharply with what he experienced earlier this season with the Minnesota Timberwolves.
Dillingham has already logged more than 20 minutes in each of his first three games with Chicago, a sign of increased trust and opportunity. More importantly, he appears comfortable with the Bulls’ pace and offensive structure, which allows him to handle the ball, create shots, and make plays for others. According to Joe Cowley of the Chicago Sun-Times, Dillingham has openly appreciated the stylistic differences between Bulls coach Billy Donovan and Minnesota’s Chris Finch.
“Just two different styles of offense — not as much holding the ball [with the Bulls],” Dillingham said. “Just, like, get off the ball. And, really, in Minnesota, it was, like, every possession.”
Dillingham also noted how freedom and tolerance for mistakes have played a role in his renewed confidence.
“I mean, every possession matters here, but you’re going to mess up,” he said. “Over there, not everyone could mess up and keep playing. So [it was] just the opportunity and the pace of the game, just the playing styles.”
Those words reflect a young player who understands how opportunity can shape development. Dillingham’s time in Minnesota did not unfold as planned, as limited minutes and inconsistent roles prevented him from finding a rhythm. In Chicago, however, he has been given a chance to play through mistakes, an essential element for growth, especially for a guard whose game relies heavily on creativity and aggression.
With 27 games remaining in the regular season, the Bulls have an extended window to evaluate Dillingham’s long-term fit. Live, in-game reps are invaluable for a player at this stage of his career, allowing him to identify areas for improvement during the offseason. Whether his minutes remain consistent once Josh Giddey and Tre Jones return from injury remains to be seen, but the responsibility will fall on Donovan to balance development with competition.
Donovan has already acknowledged both the upside and the challenges that come with Dillingham’s style of play.
“He’s the one guy who, off the dribble, can really get by people and get into the teeth of the defense,” Donovan said. “That’s a real great positive. But the decision-making, the shots he’s taking, are not sustainable, and I told him that.”
That balance between freedom and accountability will be critical as Dillingham continues to adjust. His ability to break down defenses gives the Bulls a dynamic element they have often lacked, but refining shot selection and decision-making will determine how large his role becomes.
As Chicago opens the post-All-Star break schedule against the Toronto Raptors, the Bulls sit 11th in the Eastern Conference, two games back of the final play-in spot. With nearly a third of the season still to play, the focus shifts toward development, evaluation, and momentum. For Dillingham, this stretch represents a fresh start, one defined by opportunity, trust, and a system that encourages him to play freely.
If that continues, Chicago may have uncovered more than just a deadline acquisition; it may have found a guard ready to grow into a meaningful piece of its future.