4 Biggest Needs for the Chicago Bulls in Free Agency (With Some Names to Watch)

The work has only just begun for Chicago Bulls executive Bryson Graham.

After a busy draft night, the franchise is now headed toward a huge free agency period. They will be one of only a handful of teams with significant cap space, putting them in a position to significantly shake up this roster.

To be sure, things are getting a bit crowded with the 15-man unit. But that doesn't mean we shouldn't expect some moves over the next couple of days and weeks. The Bulls have some pretty glaring roster holes to fill, and the majority of these players weren't hand-picked by Graham. This could lend itself to plenty of action, especially if there are several players this new front office likes on the market.

With that in mind, let's take some time to go over four of the biggest free agency needs for the Bulls. We will throw out a few names worth keeping an eye on, as well. And don't forget that one player could potentially check a couple of these boxes!

Starting Shooting Guard

Apr 28, 2026; Boston, Massachusetts, USA; Philadelphia 76ers guard Quentin Grimes (5) comes off the court after warming up before the start of the game against the Boston Celtics during game five of the first round of the 2026 NBA Playoffs at TD Garden. Mandatory Credit: David Butler II-Imagn Images | David Butler II-Imagn Images

With Caleb Wilson and Dailyn Swain joining the fold on draft night, the Chicago Bulls left open a spot in the backcourt. Many believed that the No. 15 pick would have gone to a guard, as this draft had its fair share of intriguing players. Bryson Graham, however, made evident that his draft night approach will have little to do with fit. The best move is always to grab the best player on your board, especially when building from the ground up.

To be sure, some have listed Swain as a guard in the past. With that being the case, particularly with so much length and versatility on this roster, we probably shouldn't rule out the idea of him suiting up at times in the two spot. Swain flashed enough ball-handling and ISO skills to make it worth a shot.

At the same time, Swain fits the mold of a forward far more with his six-foot-seven, 200-pound frame. The fact that he's also an unproven option from behind the arc doesn't make it any easier to play him in that spot. Simply put, the Bulls need more true guards, which is quite funny to say after they were overflowing in that department to end 2025-26.

A recent rumor tied Chicago to veteran guard Norman Powell, who will hit free agency this week after becoming an All-Star for the first time last year. Nevertheless, this would be a pretty shocking move considering his likely payday and the fact that he's 33 years old. Would the Bulls benefit from the addition of some savvy vets? Sure. You want guys to help set the tone on and off the court for the young players. But a run at Powell would be quite the unconventional swing for a rebuilding squad.

So, who else could be an option? The Bulls could always look to bring back Anfernee Simons, who finished last season with Chicago and made a lot of sense on-paper with Giddey. He's also considerably younger than Powell (27) and showed during the first half of last season with Boston that he could be a real winning player. The Bulls could try to ink him to a cost-effective multi-year deal and thus have another trade chip on their hands down the road.

Quentin Grimes could fit a similar profile. His career has been up and down at times, but he's shown the ability to score in bunches. The former 76ers guard provides some great positional size and would add to that hard-nosed, downhill mentality the Bulls are seemingly trying to establish.

The Bulls could also look to go the restricted free agency route. Both Bennedict Mathurin and Peyton Watson will be up for grabs and would undoubtedly fit within Bryson Graham's current timeline. Of course, you run the risk of their current team's matching, but the Bulls have the money to put some real pressure on both the Clippers and Nuggets.

Any Three-Point Shooters Welcome!

Apr 27, 2026; Denver, Colorado, USA; Denver Nuggets guard Tim Hardaway Jr. (10) before the game against the Minnesota Timberwolves during game five of the first round of the 2026 NBA Playoffs at Ball Arena. Mandatory Credit: Isaiah J. Downing-Imagn Images | Isaiah J. Downing-Imagn Images

Neither Caleb Wilson nor Dailyn Swain is known for their three-point stroke. Might they be able to develop into solid shooters? Absolutely, but that process will take time.

Josh Giddey and Matas Buzelis are in a similar situation. Both took real steps in the right direction as deep threats last season. The former, however, is never going to be a high-volume guy. As for Buzelis, he will always be at his best attacking downhill and in transition.

Tre Jones has never been a great shooter. Rob Dillingham has yet to show signs of life from long range. Patrick Williams is efficient but at times unplayable. Jalen Smith is an awesome floor-spacer for his size but could be fighting for playing time. Need I go on?

It's just staggering how little shooting there is on this current roster. And, even if this will largely be a rebuilding/developmental season, it's still wise to field a balanced basketball team to maximize growth. You want young guys playing the right way and within the right structure.

Of course, this is a problem that can be solved, in part, with the starting shooting guard. But you need more than just one guy who can chuck up shots, especially around such a deep group of forwards.

This is why there will continue to be some questions about a player like Kam Jones, whom the Bulls acquired in that trade for No. 38. He was able to shoot in college, but if they don't feel good about where things stand with him, I wouldn't be shocked if they do not guarantee his roster spot to open space for a more proven shooter.

Tim Hardaway Jr. could be one name to keep an eye on. The Nuggets' guard made a strong run at Sixth Man of the Year in 2025-26 and shot 40.7 percent on nearly 7.0 threes per game. Luke Kennard is one of the best pure shooters in the game, and we also just saw Landry Shamet have an impactful championship run with the Knicks.

Bones Hyland may be another worth looking into. He had a resurgent year with the Timberwolves, shooting 38.8 percent on 4.2 attempts a night off the bench. Still only 25 years old, he could be an acceptable flyer.

With that said, the options on the free agent market aren't fantastic. It's why we might want to watch for possible trades from Graham. Isaac Okoro, in particular, feels like someone they could look into flipping this summer.

A Backup Big Man

Apr 1, 2026; Orlando, Florida, USA; Atlanta Hawks center Jock Landale (31) reacts after a three point basket against the Orlando Magic in the third quarter at Kia Center. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

The Chicago Bulls have some serious size and length on their roster, but they are still missing that obvious backup big man.

Jalen Smith is on the roster and coming off a very strong year. However, some of his best ball was played at the four and along the perimeter. He's also not a particularly physical player or someone who can be leaned on consistently for rim protection. This is a big reason why the new front office went out and landed Nic Claxton.

Speaking of which, Claxton has also trended in the wrong direction over the last couple of seasons. He's still a worthwhile flyer for this Bulls organization, but he does have a more slender frame and can struggle at times against bigger bodies on the glass. One has to imagine the front office is well aware and thus open to grabbing a more traditional backup big.

The options may not be particularly inspiring, but there are plenty for the Bulls to consider. Andre Drummond will be back on the market and can surely help on the glass. Neemias Queta is coming off a fantastic season with the Celtics and has a player option he could turn down for a longer-term deal. Jock Landale has long been a good offensive rebounder and can stretch the floor at a solid clip.

The Bulls aren't going to swing for the fences here, especially with Claxton now in the mix. But don't be surprised if this isn't their first signing of free agency. If someone they like is willing to take a cheap one or two-year deal, they might be wise to lock that in quickly.

A Locker Room Vet

May 15, 2026; Minneapolis, Minnesota, USA; Minnesota Timberwolves guard Mike Conley (10) steals the ball from San Antonio Spurs guard Dylan Harper (2) in the first half during game six of the second round of the 2026 NBA Playoffs at Target Center. Mandatory Credit: Jesse Johnson-Imagn Images | Jesse Johnson-Imagn Images

While this might be last on the organization's priority list, it's undoubtedly something to consider over the next couple of weeks.

The Chicago Bulls are in a position to be easily one of the youngest teams in the NBA. In fact, the oldest player on the active roster right now is Nic Claxton, who just turned 27 years old in April. Can they really afford to go into 2026-27 with that being the case?

To be sure, the Bulls don't seem to have many wild cards on their roster. They have a group of high-character guys, which even includes their two newest rookies. Caleb Wilson already sounds like he's been in the NBA for a decade when opening his mouth.

At the same time, you can't rely heavily on first or second-year guys to set the tone. Even if Wilson is the kind of franchise-altering player you want him to be, you can't expect him to be an expert leader right off the bat. The same goes for Matas Buzelis, who doesn't turn 22 years old until October.

Adding a seasoned vet or two to help show guys the ropes is never a bad idea. They can usually come via the vet minimum and will likely arrive with minimal expectations in terms of playing time. We're talking about the Taj Gibsons and Kyle Lowrys of the world. They are true pros who set a standard and act as an extension of the coaching staff.

Possible options this summer could be Mike Conley, Seth Curry, Joe Ingles, and Kevin Love. All four have garnered experience playing for very young teams over the last couple of years. Again, creating a roster spot for one of these guys may not be at the front of mind for Bryson Graham, but it could make a lot of sense as we head toward October.

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