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One Offseason Decision the Chicago Bulls Might Already Regret
Jun 17, 2026; Chicago, Il, USA; Chicago Bulls Executive Vice President of Basketball Operations Bryson Graham (R) introduces Chicago Bulls new head coach Tiago Splitter (L) during a press conference at Advocate Center. Mandatory Credit: Kamil Krzaczynski-Imagn Images IMAGN IMAGES via Reuters Connect

While many NBA organizations sprint to their next destination, the Chicago Bulls are chilling in a lawn chair on a moving sidewalk.

Beginning a rebuild this offseason with a total front office overhaul, the plan for 2026-27 is to see where the momentum takes them. The Bulls added a pair of intriguing youngsters on draft night and continue to have promising pieces like Matas Buzelis and Josh Giddey to develop. They did go out and add a couple of veterans – Norman Powell and Nic Claxton – to raise their competitive floor and serve as locker room leaders. But make no mistake, the Bulls are in evaluation mode.

Despite it meaning a potentially lopsided win-loss column, it's a refreshing approach from the franchise as a whole. The team has repeatedly lived in the middle and refused to build around young talent in earnest. New executive vice president of basketball operations Bryson Graham is taking a far more methodical approach. And that's why it's hard to blame him for a relatively tamed first offseason in power.

At the same time, that doesn't mean the new front office leader had a flawless few months. This is the first time in the No. 1 seat, and there are bound to be a handful of lessons learned throughout the entirety of this Year 1.

One possible misstep is hard not to think about as training camp nears. Is it the kind that will significantly hurt their plans moving forward? Not necessarily, but it's the kind that may very well convince Graham to approach things a tad differently moving forward.

Should the Bulls Have Been a Little More Aggressive?

IMAGN IMAGES via Reuters Connect

The Chicago Cubs entered the offseason with as much financial flexibility as anyone. They were overflowing with cap space, in particular, yet they chose to use the bulk of it to add two veteran pieces. Norman Powell was signed to a two-year, $45.0 million deal, while Nic Claxton's $30+ million contract was acquired via trade. They also decided to use cap space to re-sign Zach Collins on a team-friendly two-year deal.

In a vacuum, none of those individual moves are egregious. They essentially punt the spending power down the road and serve as pretty tradeable deals. For a rebuilding team, however, it was a tad odd to not see the organization pursue any additional young talent outside the draft. And it's not as if there weren't decent options!

Early in the offseason, several respected young role players were on the move for financial purposes. Aaron Wiggins and Isaiah Joe are two who stand out from the pricey Oklahoma City Thunder. They landed with the Atlanta Hawks and Detroit Pistons, respectively, for nothing more than a couple of second-round picks.

Speaking of Detroit, they made their own move with Isaiah Stewart. The highly efficient big man was sent to the Memphis Grizzlies for another package of second-round picks.

Is it possible the Bulls now look back and regret not pulling off one of those moves? All three would make a lot of sense on this existing roster, which still lacks guard depth and long-term options at center. Both Wiggins and Joe are very capable long-range threats. Meanwhile, Stewart feels as though he has the kind of toughness Tiago Splitter is hoping to implement.

To be clear, Wiggins and Joe are both 27 years old. Stewart turned 25 at the beginning of the summer. In other words, they may not have been the youngest players on the market, but they are still the kinds who are just entering their primes and have arguably been needing more opportunity. The Bulls should be happy to welcome those players in with open arms!

Sure, acquiring any of those three would have meant sending away some second-rounders. The Bulls are in asset accumulation mode, so one can understand some slight hesitancy. But this is also a franchise with over ten at their disposal. It couldn't hurt to move a few, especially for a player who fits with what this young team needs and could thrive with more responsibility.

One has to wonder if the Bulls were waiting for an opportunity that simply never materialized. Maybe they wanted to pull off a big salary dump in exchange for first-rounders. Maybe they were thinking a different, higher-upside young player would become available.

The fact that the Bulls were even sniffing around Bennedict Mathurin and Jonathan Kuminga underscores this point. They suddenly found themselves with an open roster spot and very few reasonable options on the board. Sometimes the grass isn't always greener, and moves around the margins can be the ones worth taking.

Once again, no one is saying that this is some kind of big blunder, but the NBA is all about taking advantage of opportunities when they appear. Graham may want to be a little more aggressive with his decision-making moving forward.

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This article first appeared on Chicago Bulls on SI and was syndicated with permission.

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