CHICAGO — Rob Dillingham’s voice occasionally tremors while he recalls his time in Minnesota. He looks off into the distance, searching for answers — namely, what went wrong — though they’ve circulated in his mind for much of the past two seasons.
Dillingham was the No. 8 pick in the 2024 NBA Draft, acquired by the Timberwolves in a draft-night deal with the San Antonio Spurs. He felt the weight of his position almost immediately. The burden of his projections as heir to Mike Conley’s point-guard duties on a contender. The idea of him came as someone who could take pressure off superstar engine Anthony Edwards.
Minnesota needed to assign responsibility. Windows of Western Conference relevance wait for no one, not even a lottery pick.
The Wolves traded the 21-year-old Dillingham, along with Leonard Miller and four second-round picks, to the Chicago Bulls for Ayo Dosunmu and Julian Phillips on Feb. 5. Since then, Dillingham has appeared in all 11 of Chicago’s games, playing at least 20 minutes — his previous season high in Minnesota — in eight of them.
“When you do (play), you gotta play perfect in your opportunity, or you won’t get more opportunities,” Dillingham told The Athletic when asked to describe the pressure he felt in Minnesota. “The pressure really comes from whenever you come out of college or come from wherever; you play freely because you know you get minutes. But in the NBA, it’s not like that. It’s you switching your whole mindset to ‘I gotta perform well in these minutes.’
“Your whole life, you just played basketball. You messed up, but you learned from mistakes. With me, I’m a smaller guard, so it was way less room for mistakes. And, s—, you gotta own up to that at that point. So, I feel like the pressure really comes from not knowing when you’re gonna get the opportunity.”
Dillingham only ever sought ways to simulate life as a professional. In high school, he opted to play in the Overtime Elite league, a prep syndicate that contracts its players. He then enrolled at Kentucky to play under John Calipari, known for nurturing pros and churning out NBA guards.
When he reached the NBA, Dillingham endured what he described as “trust struggles.” Looking over his shoulder, expecting a turnover or missing a shot might reel him back to the bench.
Minnesota sought stability. It required playmaking away from Edwards, some ballhandling Band-Aids for the moments the All-Star faced four-on-three coverages. Dillingham proved to be a ways away from that.
“He’s young. He’s going to be a really good player in this league. It’s just going to take some time,” Wolves coach Chris Finch said. “His timeline is probably a little bit behind where we needed it to be. He’s just going to have to figure out who he’s trying to be in the league. A lot of that is normal, young player growing pains for him. It wasn’t really an indictment on him as much as we had a chance to go out and get somebody who was plug and play.”
Dillingham is listed at 6 feet 2 and 175 pounds. His handle is both his redeeming trait and what traps him in the half court. At times, once his dribble earns him a path downhill, it often appears his decision-making lags behind his speed.
He merely hoped for a chance to harness his erratic playing style, to tame his trepid tendencies with developmental minutes the Wolves couldn’t find amid all the urgency. When those minutes came, his head constantly swiveled in fear.
He remembers a time when Wolves guard Donte DiVincenzo got injured. Dillingham’s minutes came with a clear head then.
“I didn’t really think of messing up,” Dillingham said. “It was a point where I knew I could play basketball. But then, when Donte was coming back, it was more like a reality (check). Like, all right, I gotta perform well to play when he gets back. Then, mentally, I just started playing worse during that stretch.
“And after that, I just didn’t play.”
The minutes dwindled. From Dec. 29 to Jan. 29, he averaged just a little more than five minutes in nine games played. Dillingham’s conviction dwindled, too.
“I feel like if you’re human, you definitely gonna second-guess (yourself) if you working hard at something every day, and then you don’t really get an opportunity,” he said. “You start to question, like, dang, am I really good at basketball?”
These Bulls, in the business of hoarding and refurbishing former lottery picks, didn’t just inherit the Wolves’ project. They’re tasked with developing more than his game. To extract whatever potential Dillingham might possess, a reconstruction of his belief and trust must take place, too.
“Not playing is a low point for me every day, especially for me,” Dillingham said. “Basketball is, like, my safe place. Whenever basketball ain’t going right, I honestly don’t care about money. I care about basketball, so that really drives me crazy. The whole time (in Minnesota), I was mentally drained, but I feel like it makes you more thankful when you do get an opportunity. If you get it all at one time, then you’re not gonna be as thankful for it.”
Rob Dillingham’s questionable decision-making led to a lot of time on the bench in Minnesota. (Jesse Johnson / Imagn Images)
The stakes are different in Chicago. Dillingham joins an incoherent group, mostly composed of guards, with varying motivations. Two guards who joined him at the trade deadline — Collin Sexton and Anfernee Simons — are veterans on expiring contracts, aiming to audition for next season. Another, Jaden Ivey, fits a similar timeline to Dillingham’s, though he’s sidelined while attempting to strengthen his leg. All three, when healthy, have comfortably exceeded Dillingham’s 19.3 minutes per game for a Bulls staff that continues to lean on veterans despite a roster whittled down to a reset.
Chicago traded away any hint of cohesion, weary of a middling cycle that perpetually sent it to the Play-In Tournament. In most cases, a 21-year-old with two years remaining on a rookie-scale contract, who also essentially arrives as a blank canvas, might be home free.
But coach Billy Donovan has never granted opportunity easily.
Still, when Dillingham discusses the differences between his new and former staff, he perks up. He notes he’s rejuvenated by the way they communicate with him.
“They’re building me up,” Dillingham said. “It’s more like I can mess up, and they teach me after I mess up, what not to do, why not to do this. … I get to actually perform and learn and watch film here and watch where I play.”
Dillingham’s game remains volatile. He’s perhaps the best on the roster at breaking down defenders with the dribble. His quickness and herky-jerky rhythm define his game. But it often appears like the game is moving too fast for him, and that he’s moving too fast for his own good. He bullets every pass he throws, targets narrow windows and, since joining the Bulls, is shooting just 38 percent from the field and 16.7 percent from 3 entering Sunday’s game in Sacramento.
Through his continued development, Dillingham isn’t asking for much.
“Really, just communication. Honesty,” Dillingham said. “I feel like any person, if you say something, you stick to your word, and that’s what it is. There’s no reason (for) beating around the bush or telling someone something if it’s not gonna help them. I’d rather you just tell me exactly what it is, whether it’s positive or negative, and then from there, it’s up for me to fix it.
“If there’s no transparency, then your player’s not going to go that extra mile for you. They’re going to go the extra mile for themselves.”
To that end, Donovan’s critiques have been clear: Improved decision-making is paramount if Dillingham is to find staying power in the NBA. And for the first time in his pro career, Dillingham knows what’s required of him.
“When I know what you want from me or what I need to do, then it’s easier for me to help the team,” Dillingham said. “If I’m guessing, then it’s hard. And I feel like since I’ve been here, (Donovan) has done a great job just communicating to me, telling me what he feels like I can do to stay in the league and be a force in the league.”