Rob Dillingham’s NBA journey hasn’t exactly followed the script many expected when he was taken with the No. 8 pick in the 2024 NBA Draft. But after a rocky start in Minnesota, the young guard may finally be finding his footing - this time in Chicago.
Let’s rewind for a second. The Timberwolves moved up to draft Dillingham with the hope that he could help solidify their backcourt, especially after their playoff loss to the Dallas Mavericks exposed a need for more dynamic guard play.
But that opportunity never materialized. Before training camp even tipped off, Minnesota added Donte DiVincenzo and Julius Randle - two ball-dominant players who immediately complicated Dillingham’s path to playing time.
Add in the presence of All-Star Anthony Edwards and the veteran Mike Conley, and it was clear Dillingham was buried on the depth chart before he even had a chance to prove himself.
To make matters worse, Bones Hyland - who entered the season on a non-guaranteed deal - outperformed expectations and leapfrogged Dillingham in the rotation. That left Rob as the fifth guard in the pecking order, relegated to garbage time minutes and occasional spot duty when injuries struck. The numbers reflected the lack of rhythm: 3.5 points, 1.7 assists per game, and shooting splits that never found their footing - 33.3% from the field, 36.4% from three.
Fast forward to the trade deadline, and Dillingham found himself on the move, part of the package that sent Ayo Dosunmu to Minnesota. For Dillingham, the trade to Chicago may be the break he’s been waiting for.
Now, let’s be clear - the Bulls aren’t exactly lacking in guards either. Heading into the deadline, the expectation was that Chicago would look to clear up its backcourt logjam.
Instead, they made some eyebrow-raising moves that only added to the congestion. Coby White was traded, but Collin Sexton came back.
Kevin Huerter was shipped out, but Jaden Ivey came in. Even Nikola Vucevic’s exit brought in Anfernee Simons - another guard who thrives with the ball in his hands.
So yes, the backcourt is crowded. But here’s the difference: the Bulls aren’t chasing a title right now. They’re in a transition phase, which gives players like Dillingham something they didn’t have in Minnesota - room to grow, and more importantly, room to make mistakes.
And in his first two games with the Bulls, Dillingham has already started to show flashes of what made him a top-10 pick. In his debut, he logged a season-high 22 minutes, putting up nine points and four assists while finishing as a +9 in a 16-point loss.
That’s not nothing. In his second outing, he matched those 22 minutes, this time contributing eight points, seven rebounds, and two steals - again finishing with a positive plus-minus (+7).
It’s early. It’s a small sample size.
But for the first time in his young career, Rob Dillingham is getting real minutes and real opportunities. And if the Bulls are willing to be patient - to let him learn on the fly - there’s reason to believe they might have something special on their hands.
He’s not going to come in and take over games right away. That’s not the expectation.
But in a league that thrives on pace, creativity, and shot-making, Dillingham has the tools to carve out a meaningful role. All he needed was a chance.
Now that he has one, it’s going to be fun to see what he does with it.