Rob Dillingham’s Fresh Start in Chicago Is Exactly What He Needed
Rob Dillingham’s rookie season didn’t exactly go as planned in Minnesota. Drafted as a lottery pick with high expectations, the young guard found himself buried on a Timberwolves team with playoff ambitions and little patience for growing pains.
That’s a tough spot for any 21-year-old, especially one still adjusting to the speed and physicality of the NBA. In that environment, every mistake felt magnified - and for a player whose game thrives on rhythm and confidence, that’s a recipe for frustration.
But now, in Chicago, Dillingham is getting something he never really had in Minnesota: room to breathe.
The Bulls, currently in a transitional phase and clearly prioritizing development over wins, have given Dillingham a green light to learn on the job. That means playing through mistakes, experimenting with his game, and most importantly, getting consistent minutes. He’s logged over 20 minutes in each of his first three games with the Bulls - a clear sign that the coaching staff wants to see what he can do when he’s not looking over his shoulder after every turnover.
And make no mistake: the upside is still very real.
Why Dillingham Was a Lottery Pick in the First Place
Let’s not forget, Dillingham wasn’t just a lottery pick - he was widely considered one of the steals of the draft when Minnesota landed him. A dynamic scorer with elite quickness and a natural feel for playmaking, he flashed serious potential at Kentucky.
The tools are all there: the handle, the vision, the ability to create off the dribble. But in Minnesota, the fit just wasn’t right.
The team’s win-now mentality didn’t leave room for a developmental project at point guard, and Dillingham never got the runway he needed.
Chicago, though, is a different story. With the team clearly in rebuild mode, the Bulls can afford to take a long look at their young talent.
They’ve already exercised Dillingham’s club option for next season, and they’ve got another one lined up for 2027-28. That gives the front office time - and flexibility - to see if the former Kentucky standout can grow into a long-term piece.
And early signs are promising.
In what was arguably his best game of the season so far, Dillingham dropped 16 points, dished out 7 assists, and picked up 3 steals - a well-rounded performance that showcased his ability to impact the game on both ends. Sure, there were still some rookie mistakes, but that’s part of the process. The important thing is he’s getting the reps and showing flashes of what made him such an intriguing prospect in the first place.
Navigating a Crowded Backcourt
Of course, it’s not all smooth sailing. Dillingham’s path to consistent minutes is complicated by a crowded Bulls backcourt.
Jaden Ivey and Anfernee Simons are both on expiring deals and playing for their futures, while Collin Sexton remains very much in the mix. That’s a lot of mouths to feed in a rotation that only has so many guard minutes to go around.
So while Dillingham has more freedom in Chicago than he did in Minnesota, he’s still competing for time - not against the expectations of a playoff team, but against other young guards trying to prove they belong.
That said, this is the kind of challenge that can sharpen a player. If Dillingham can carve out a role in this environment - one that values development but still demands production - it’ll say a lot about his trajectory moving forward.
The Bulls Might Have Something Here
Right now, Chicago isn’t chasing wins. They’re chasing answers. And Dillingham, with his mix of raw talent and untapped potential, is exactly the kind of player who could turn into a long-term solution - or at the very least, a valuable asset.
Whether he becomes the Bulls’ point guard of the future or simply a sparkplug off the bench, this stretch is crucial. He’s finally in a situation where growth is the goal, not just a bonus. And if he keeps stacking performances like the one he had Wednesday, it won’t be long before the Bulls - and the rest of the league - start taking serious notice.
For now, the spotlight is his. Let’s see what he does with it.