This franchise is at a crossroads, but for the first time in a long time, that uncertainty feels intentional. The Bulls are no longer pretending to be something they aren’t. Instead, they are evaluating, experimenting, and gathering information on which players belong in the next iteration of Bulls basketball. Two foundational pieces are already in place: Matas Buzelis and Josh Giddey. Both are under team control for the next few seasons, and the organization has made it clear that the offense is meant to flow through them. Giddey’s pass-first instincts and Buzelis’ versatility give the Bulls a framework to build around. Now comes the hard part: finding the right complementary pieces in a star-driven league.

At the trade deadline, Chicago added a wave of young, talented guards: Anfernee Simons, Jaden Ivey, Collin Sexton, and Rob Dillingham. Each comes with a different timeline and set of questions: Simons and Sexton are on expiring deals and will be unrestricted free agents at season’s end. Ivey is headed for restricted free agency, giving the Bulls the right to match any offer. Dillingham, meanwhile, is a recent first-round pick under team control for several more seasons. He is a long-term evaluation project who simply needs reps.

This season (and maybe even next) isn’t about immediate results. It’s about figuring out who fits.

My Hottest Take: Extend Anfernee Simons

If the Bulls are going to try to fill out a competitive roster next season, Anfernee Simons is the best bet among the guards they acquired.

When given consistent minutes and usage, Simons has proven he can score at a high level, eclipsing 20 points per game while keeping an offense functional. His time in Portland came during a rebuild, so the lack of winning context shouldn’t be mistaken for a lack of ability. If anything, that experience makes him an interesting reclamation candidate in a more structured environment.

Simons turns 27 on June 8, and there is still plenty of basketball ahead of him. A fresh start in Chicago could be exactly what he needs. His current deal pays him roughly $27 million, and he is set to hit free agency at the end of the season. With the Bulls sitting at 24–31 and 11th in the Eastern Conference, the remainder of the year serves as an extended trial run.

The fit with Josh Giddey is particularly intriguing. Giddey thrives with the ball in his hands as a creator, and Simons is most effective when he can operate as a scoring guard who doesn’t have to initiate every possession. If Simons can consistently space the floor, attack closeouts, and shoulder the scoring load, he could carve out a long-term role alongside the team’s core.

Defense remains the biggest question mark. Simons has never been known as a stopper, but in the right scheme and in a situation where he isn’t asked to do everything offensively, his weaknesses could be mitigated. Chicago doesn’t need him to be elite defensively; they need him to be reliable, engaged, and accountable.

If Simons proves he can thrive next to Giddey and Buzelis, extending him could provide stability during a critical phase of the rebuild.

What You Need to Know: Dillingham Has Already Flashed Talent

Sometimes, being in the right place at the wrong time changes everything. That was the case for Rob Dillingham in Minnesota. The Timberwolves were in win-now mode and couldn’t afford to develop a young guard who didn’t fit their immediate timeline. As a result, Minnesota moved Dillingham, Leonard Miller, and four second-round picks to Chicago in exchange for Ayo Dosunmu and Julian Phillips on February 5, 2026.

Early returns have been encouraging. In his first three games with the Bulls, Dillingham has flashed scoring ability, playmaking instincts, and defensive activity. In roughly 24 minutes per game, he’s averaging 11 points, four assists, and two steals, showing the kind of energy and creativity that made him a first-round pick in the first place.

At 21 years old, Dillingham is still very much a work in progress. His biggest limitation is his size—at 6-foot-1, he’ll always face challenges defensively. But if surrounded by the right personnel, he can still impact games through quick hands, anticipation, and transition play.

Most importantly, Chicago can give him something Minnesota couldn’t: opportunity. This season is about letting players fail, adjust, and grow—and Dillingham fits that timeline perfectly.

Before You Go: There Will Be Moments of Joy

An identity shift is never smooth. There will be ups and downs, frustrating stretches, and nights where the results don’t reflect the effort. But Bulls fans know what this team looks like when it’s right, and there are few atmospheres in sports like a buzzing United Center when Chicago is winning.

Buzelis and Giddey represent hope and flexibility. The front office now has the freedom to mold a roster around them instead of forcing short-term fixes. If the Bulls make smart decisions with the pieces they’ve acquired, the payoff will come.

It may not be fun every night—but the moments of joy will remind fans why it’s worth the wait.