Guard Logjam Creates Chicago Bulls' Biggest Post Trade Deadline Concern

The Chicago Bulls and Billy Donovan have entered unfamiliar territory.

The head coach has never been one for a rebuild. After a historic run with the University of Florida, he arrived in the NBA ready to compete for a title. The Oklahoma City Thunder were among the most fascinating teams in the Western Conference, built around the dynamic duo of Russell Westbrook and Kevin Durant.

Even after the organization watched Durant join forces with the Golden State Warriors and Westbrook end up in Houston, Donovan pushed full steam ahead. He coached an uncharacteristic three-guard lineup of Chris Paul, Shai Gilgeous-Alexander, and Dennis Schroder into a first-round playoff series. Then, with the Thunder finally ready to take a step backward and prioritize their future, Donovan walked out the door.

He showed up in Chicago ready to compete. Both he and front office leader Arturas Karnsovas preached a win-now philosophy that led to some aggressive roster moves. This mindset only continued despite the franchise's lackluster results ... until now.

After years of fans calling for a roster teardown, the front office did just that. They showed seven players the door, loading up on expiring contracts and second-round picks in the process. All things considered, the moves reflected those of a rebuilding organization. In other words, something Billy Donovan has never been a part of.

It begs the question: Are the Chicago Bulls and Billy Donovan still on the same page? Is the head coach ready to focus on development and lottery odds instead of a Play-In Tournament push? If not, the Bulls could be in for a problematic final month and a half of the regular season.

How Will Billy Donovan Split Up Minutes?

Billy Donovan of the Chicago Bulls — Jan 22, 2026; Minneapolis, Minnesota, USA; Chicago Bulls head coach Billy Donovan looks on against the Minnesota Timberwolves in the first half at Target Center. Mandatory Credit: Jesse Johnson-Imagn Images | Jesse Johnson-Imagn Images

The Chicago Bulls' front office didn't make it easy on Billy Donovan with their deadline moves. The team loaded up on guards, adding Anfernee Simons, Collin Sexton, Jaden Ivey, and Rob Dillingham to the roster. The first two are veteran scorers on the hunt for a fresh payday. The latter two are former lottery picks in desperate need of developmental minutes.

Up until this point, Donovan has had it somewhat easy. All four have been able to clock around 25+ minutes a night. However, what is going to happen when Josh Giddey and Tre Jones are given the green light to return? Both are seemingly heading in that direction and could be back on the court as soon as this week.

If the mission is to win as many games as possible, letting the more experienced Simons and Sexton run wild with Giddey and Jones is likely the right call. But in no way does that feel like it is the best long-term interest of the organization. Instead, seeing what you have in Ivey and Dillingham is paramount. The 24-year-old is headed toward restricted free agency in a matter of months, while the 21-year-old Dillingham still has a year left on his current deal.

More specifically, seeing how both those players fit with core pieces like Giddey and Buzelis is key. They can't merely be checking in off the bench or during mop-up minutes. They need to clock meaningful time on the court for the Bulls to evaluate what they can bring to the table. The only way to ensure that happens with a healthy Giddey and Jones is to limit both Simons and Sexton. Do the Bulls have that in them? Better yet, does Donovan?

On the one hand, moving Ivey to the bench in the game before the All-Star break raises a red flag. The same can be said about his comments regarding the rawness of Dillingham's game:

“It’s not like I’m giving him free rein. We need him downhill, but he also can’t be jumping off of two feet, getting caught in the air, shooting over guys, trying to throw passes that aren’t there," Donovan said last week (h/t Joel Lorenzi). "He’s gotta clear that up, and we’ve gotta help him do it. But what I don’t want to do is have him not be aggressive where he’s [like]. ‘I’m afraid to attack.’ He has to attack, but he’s gotta make better decisions. I think that will come in time.”

On the other hand, Donovan did still play both Dillingham and Ivey more than Simons and Sexton in that last meeting, despite the veterans starting. He has also been rather blunt about how hard the next few weeks will be, implying that he's well aware of the losses that will stack up. Comments about a Play-In push have been nonexistent.

Actions always speak louder than words, though. Donovan is on the brink of having to make some very tough decisions regarding his rotation. What he does will tell us a lot about the Bulls' true intentions, as well as whether he can remain the right guy for the job moving forward.