Bulls Still Have an Obvious Roster Void to Fill After Losing Anfernee Simons

The Chicago Bulls enter the third day of free agency with a glaring weakness.

Expectations for the win-loss column may not be high for the 2026-27 season, but Bryson Graham and his new front office have every reason to construct a cohesive roster. The organization is trying to establish a new identity and culture. Just as important, they now have multiple youngsters with star-level upside to develop. The best way to do that? Play good basketball.

The good news is that the current roster is overflowing with athleticism. This group is built to attack in the open floor and put constant pressure on the paint. They have an intimidating size and length at essentially every position, which could prove to be a great fit for new head coach Tiago Splitter.

Also, to Graham's credit, he inked one of free agency's best long-range shooters. Not only will Norman Powell provide necessary veteran leadership, but his floor spacing and secondary ball-handling were much-needed. Having so many talented forwards who are at their best going downhill, Powell's presence will only give them more room to work. Opposing defenses can't leave open a career 40.0 percent three-point shooter!

Nevertheless, as helpful as Powell may turn out to be, is one shooter ever enough? The Bulls can't lean solely on the veteran's hot hand, which is why some real pressure resides on this 15th and final roster spot.

This is especially true after the Bulls missed out on retaining Anfernee Simons. To be sure, it's unclear how hard Graham worked to keep the former Celtics sixth man around. However, doing so would have made a ton of sense for this current group. Simons would have given them a high-volume threat off the bench, as well as someone who could even play alongside Powell at times.

The Bulls also still have their $9.4 million room exception available to spend on these last remaining roster spots. It's a decent chunk of change – one that felt like it would be enough to bring Simons back the longer he was sitting on the market.

Fast forward to Thursday, and ESPN's Shams Charania reported that Simons inked a two-year, $12.3 million deal with the Philadelphia 76ers. While the deal brought Simons back to a contender, it came with a shockingly cheap price tag. The Bulls could have beaten the $6.2 million AAV pretty easily, making it feel like a big missed opportunity.

So, where do the Bulls turn now? Who else could fill this shooting void? It's slim pickings.

A Few Shooters for the Bulls to Target

May 23, 2026; Cleveland, Ohio, USA; Cleveland Cavaliers guard Max Strus (2) reacts in the third quarter against the New York Knicks during game three of the eastern conference finals for the 2026 NBA playoffs at Rocket Arena. Mandatory Credit: David Richard-Imagn Images | IMAGN IMAGES via Reuters Connect

Earlier this week, we listed Gary Trent Jr. as a reasonable option for the Bulls, and the former Bucks guard remains available. He has shot 38.7 percent from downtown over his career, proving to be a very streaky reserve.

The only problem is that he's become a pretty one-dimensional player as the years have gone on. The defense isn't what it once was, and he's not going to offer much as a facilitator. Still, on a cheap one-year deal, the Bulls could do worse than the experienced shooter.

Josh Okogie is another name we mentioned this week. Known far more for his defensive versatility, Okogie has at least been serviceable from deep over his career. He's also another respected veteran who has played in a handful of different environments.

Would the Bulls ever take a chance on the off-injured Bradley Beal? It may sound crazy, but we all know he can shoot the rock. The same goes for former Bucks All-Star Khris Middleton. To be sure, my money wouldn't be on either, but the Bulls aren't in a position to be all that picky. If one of those vets has interest in a minimum one-year deal, it might be worth considering.

Of course, we also can't rule out a possible trade! Max Strus of the Cavaliers has been connected at times to Chicago, as Cleveland may be looking to save some money. The former DePaul product could make sense as a 37.0 percent shooter over his career. To be sure, he wouldn't fit into the room exception, as he's owed $16.7 million this season, though it shouldn't be too difficult for the Bulls to make it work.

It's also not out of the question that the Bulls choose to leave the roster spot open heading into camp. While they probably look to fill it before then, they did add a couple of college sharpshooters to their Summer League squad. Jaylin Sellers, out of Providence, signed a two-way deal, so they could wait to see if he's worth elevating to a full-time roster spot.

Regardless, if one thing is for sure, I would be shocked if Bryson Graham didn't use this final roster spot to further address the lack of shooting. The Bulls have solid depth at the wings and in the frontcourt, but the backcourt needs an extra body. It's a surprising thing to say after how 2025-26 ended, however, it speaks to the fact that this is a very new front office with very different priorities.

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