Chicago Bulls May Be Ready to Give Rob Dillingham the Confidence He Needs

CHICAGO – Standing in a Chicago Bulls pinnie jersey for the first time, Rob Dillingham was brutally honest.

The guard was wrapping up his first pre-game shootaround at the Advocate Center. It was only a few days prior that the Minnesota Timberwolves chose to send Dillingham to Chicago as part of their trade package for Ayo Dosunmu. Two years prior, this transaction would have shocked the NBA world. Today, it makes all the sense in the world.

"It's a little overwhelming. For anybody, change where you live, change your teammates," said the mild-mannered Dillingham. "But, honestly, I feel like the team has made it easy for me. Coach has made it easy for me. Talked to me directly. I'm just happy to be here."

The guard was among the most highly touted prospects in the 2023 NBA Draft. He provided an incredibly efficient scoring season as a Kentucky Wildcat – the kind that is extremely abnormal for a freshman, no matter their class rank. With the Timberwolves in clear need of a backcourt partner for superstar Anthony Edwards, taking a chance on Dillingham No. 8 overall felt like a borderline no-brainer.

Rob Dillingham of the Kentucky Wildcats — Mar 6, 2024; Lexington, Kentucky, USA; Kentucky Wildcats guard Rob Dillingham (0) drives to the basket during the second half against the Vanderbilt Commodores at Rupp Arena at Central Bank Center. Mandatory Credit: Jordan Prather-Imagn Images | Jordan Prather-Imagn Images

Turns out, however, that dropping a 19-year-old onto a team with NBA Finals aspirations can come with its hiccups. While the environment can not sum up all of Dillingham's struggles – his size, for instance, remains a real concern – there is no question that it created a hurdle. He needed developmental minutes that the win-now Timberwolves could not offer. He needed someone to show they believed in him.

The Bulls did that on February 5. Becoming a recent haven for former castaway lottery picks, Dillingham is set to be their latest reclamation project. He may have been added to a comically long list of guards on the roster, but all signs point toward him sitting near the top of the priority list alongside fellow former college standout Jaden Ivey.

Nonetheless, it's going to take more than a simple change of scenery for Dillingham to become the player many once thought he could be. And the guard said as much in his initially blunt comments to Chicago media.

“Really just confidence, confidence from my teammates, confidence from my coaches, and really confidence in myself," Dillingham said when asked what he needs to take the next step. "I really just feel like I haven’t gotten to get a super opportunity where I feel confident. So really just gaining that back and understanding that I’ve been working the whole time, so it’s not like it just automatically left where I wasn’t as good. I’m just waiting for that spark to come back.”

Finding that spark can be hard to do, particularly as the Chicago winds continue to blow in mediocrity. But it's also this kind of honesty that is needed for both Dillingham and the Bulls to move forward. The organization needs to know where the 21-year-old stands physically and mentally as this new era begins. And if it's confidence he needs, it's confidence the Bulls must instill.

The Rob Dillingham Project Starts Now for Chicago Bulls

Rob Dillingham of the Chicago Bulls — Dec 12, 2025; San Francisco, California, USA; Minnesota Timberwolves guard Rob Dillingham (4) looks to pass the ball against the Golden State Warriors during the third quarter at Chase Center. Mandatory Credit: Robert Edwards-Imagn Images | Robert Edwards-Imagn Images

To the Chicago Bulls' credit, they wasted no time giving Rob Dillingham the opportunity he seemingly craves.

The guard was available for the first time during Saturday night's battle with the Denver Nuggets. While the newly acquired Collin Sexton and Nick Richards checked in off the bench first, Dillingham heard his name called with 3:39 left to go in the first quarter. It was only his ninth time this season playing in the opening frame.

What followed may not have been the most eye-popping performance, but it was the kind that got better as the minutes went by. Dillingham drilled the triple that gave Chicago a surprise 46-44 lead over the Denver Nuggets in the second quarter. Then, he sliced through the Denver defense before finding a cutting Matas Buzelis for the slam. His bounce pass feed to Isaac Okoro roughly 30 seconds later helped the Bulls even the score in the third.

Later in that same quarter, he weaved past multiple Nuggets before sending a tear-drop alley-oop to the cutting Nick Richards. He followed that up by pushing the tempo in transition and going right into the chest of Christian Braun for a trip to the charity stripe.

Really fun set up here from Rob Dillingham. That’s what you like to see in Game 1.

(🎥 @CHSN_Bulls)
pic.twitter.com/CmZH0ybsuO
— Elias Schuster (@Schuster_Elias) February 8, 2026

Dillingham finished the night with 9 points, 4 assists, 3 rebounds, and 1 steal. Again, was it the kind of outing that convinced anyone he was destined for a breakout in Chicago? No. But you noticed Dillingham for all 22 minutes he was on the floor, which also marked his season-high. This alone was an encouraging sign, and the man of the hour agreed.

“A little bit toward the end," Dillingham said after the game about feeling more confident (h/t Joel Lorenzi). "I'm really just happy I get to play. Play basketball, play hard, actually get to go out there. Definitely felt a lil spark, but got to keep it going.”

Dillingham is right; Saturday was only Game 1 of what will be a long road to proving himself as a meaningful NBA contributor. The good news, though, is that it sounds like he has been given reason to believe that opportunities will continue to present themselves. Billy Donovan has kept a tight leash on his young players in the past, but Dillingham's comments suggested that the next 28 games could be different.

“Obviously, we want to win. But we can mess up here. It’s not like, if we lose, you die," Dillingham laughed (h/t Will Gottlieb). "Here playing with my teammates, everyone is new. Really they all just gave positive comments, positive thoughts, giving me confidence. Even coach giving me confidence, so playing with everyone it’s great for sure."

To be sure, the Bulls' welcoming back Josh Giddey and Tre Jones from their respective hamstring strains will only crowd the backcourt further. Exactly what this will mean for Dillingham's minutes will be something to monitor closely. However, all he can do is take advantage of this increased playing time for now, and his next chance to do precisely that will be Monday night in Brooklyn.