Rob Dillingham, the eighth overall pick in the 2024 NBA draft, found himself traded from the Minnesota Timberwolves to the Chicago Bulls in a deadline deal involving Ayo Dosunmu. The move came after Timberwolves head coach Chris Finch had evidently lost confidence in the young guard. Since joining the Bulls, Dillingham has embraced the fresh start, eager to prove his worth amid a challenging transition.
In just his first three games with the Bulls, head coach Billy Donovan has entrusted Dillingham with significant playing time, marking a sharp increase from his limited minutes in Minnesota. The guard logged 22 minutes in his Bulls debut against Denver, repeated that tally against Brooklyn, and then played 30 minutes in a tough outing against Boston. This contrasts starkly with his January average of just 5.3 minutes per game and only one 20-minute performance all season while with the Timberwolves.
Adjusting to a Different Style and Pace of Play in Chicago
Dillingham recognizes that the offensive philosophy under Donovan differs substantially from what he experienced in Minnesota. The Bulls’ system emphasizes quicker ball movement and pushing off the ball more, creating a faster pace that contrasts with the Timberwolves’ more possession-heavy approach.
Just two different styles of offenses, not as much holding the ball (with the Bulls),
Dillingham said.
Just like get off the ball and really like in Minnesota it was like every possession … I mean every possession matters here, but you’re going to mess up. Over there it was just like not everyone could mess up and keep playing, so just the opportunity and the pace of the game, just the playing styles.

This shift has allowed Dillingham to operate with more freedom and opportunities to showcase his strengths as a dynamic ball-handler, a quality Donovan has noticed and values despite some of his rookie mistakes.
Billy Donovan’s Approach to Developing Dillingham
Donovan appears committed to nurturing Dillingham’s confidence while balancing the need for discipline and improved decision-making. He has given the second-year guard ample court time, partly driven by necessity due to sidelined guards Josh Giddey and Tre Jones, both nursing hamstring injuries.
He’s the one guy that off-the-dribble that can really get by people and get into the teeth of the defense,
Donovan stated.
That’s like a real great positive. But the decision making, the shots he’s taking, are not sustainable, and I told him that.
Donovan’s willingness to tolerate early errors comes with clear expectations for growth.
His job and responsibility is to generate shots for guys when he gets (inside) and understand the shots where he has angles and can shoot a high percentage on and the shots he can’t,
Donovan explained. “It’s not like I’m giving him free rein, we need him downhill, but he also can’t be jumping off two feet, getting caught in the air, trying to shoot over guys, trying to throw passes that aren’t there. He’s got to clean that up and we’ve got to help him do it.
What I don’t want him to do is not be aggressive or be afraid to attack. He has to attack. He just has to make better decisions, and I think that will come in time.
As Josh Giddey and Tre Jones work back toward health through three-on-three scrimmages, Dillingham’s role may tighten, signaling a need to make every minute on court count.
Dillingham’s Perspective on Building Experience and Confidence
For Dillingham, the new environment also means gaining valuable experience through repetition and exposure to NBA competition. After limited opportunities in Minnesota, he now relishes increased responsibility despite the pressure.
(Last week) was my first time playing against the Celtics and actually having the ball in my hand,
Dillingham recalled.
If I play against the Celtics three, four more times, by the time I play them the fifth time I already played them so many times that I know how to play against them. It comes with experience, studying film, and taking that into the next game.
This mindset highlights his understanding that confidence and skill development go hand-in-hand over time and exposure to the league’s pace and physicality.
The Importance of This Transition for Dillingham’s Future in the NBA
Rob Dillingham’s trade to the Bulls offers a crucial second chance to realign his career trajectory after a difficult start. Billy Donovan’s measured approach aims to harness Dillingham’s strengths while honing his decision-making skills under pressure, setting the stage for potential growth. With seasoned players recovering and competition for guard minutes set to intensify, Dillingham must capitalize on the opportunity to prove he can be a consistent contributor in the NBA.
This redemption narrative will be closely watched by Bulls fans and NBA observers alike, as Dillingham’s development could shape the team’s future backcourt dynamics and his own standing as a promising young guard.
