The Chicago Bulls are entering the 2025-26 NBA season with renewed optimism and a sense of unfinished business. After missing the playoffs once again last season, the franchise has now gone seven years out of the last eight without postseason basketball. Yet, there’s something different about this year. For the first time in a while, the Bulls made a series of decisive and promising moves during the offseason, laying a foundation that suggests they’re ready to compete.

By re-signing key free agents such as Josh Giddey, Tre Jones, and Emanuel Miller, as well as keeping Jevon Carter under contract, Chicago showed a level of stability that has often eluded them in past summers. Giddey, the most important of the group, remains the centerpiece of the Bulls’ future, a 22-year-old guard who nearly averaged a triple-double last year and is poised to become the franchise’s long-term lead playmaker.

Surrounding him, Coby White and Matas Buzelis represent youth and upside, while Nikola Vucevic continues to provide the veteran presence that the Bulls rely on inside.

The Bulls didn’t just stand pat either. They swung a notable trade, sending Lonzo Ball to Cleveland in exchange for defensive specialist Isaac Okoro, shoring up their perimeter defense and giving them a wing stopper they sorely needed. They also added Noa Essengue with their draft pick, a move that could pay dividends long-term if the young forward develops as projected. Taken together, this was a strong offseason for Chicago, one that bolstered its rotation while keeping its cap sheet flexible enough to allow for future maneuvers.

And that’s where the intrigue lies. Despite improvements, the Bulls remain a team hovering between play-in aspirations and genuine playoff contention. In a weakened Eastern Conference, where the Milwaukee Bucks and Boston Celtics still lead the pack, but several other teams have taken a step back, Chicago has a golden opportunity.

With the right in-season trade, they could vault into the playoff picture and perhaps even cause trouble in the first round. Three names stand out as realistic and transformative trade targets: Jonathan Kuminga, Anfernee Simons, and Walker Kessler.

Jonathan Kuminga: The 2-way wing the Bulls desperately need

Chicago has long lacked a true two-way forward who could serve as the connective tissue between their backcourt and frontcourt. Jonathan Kuminga, currently in a stalemate contract situation with the Golden State Warriors, fits that mold perfectly. At 23 years old, Kuminga has shown flashes of star potential but remains caught in the crowded wing rotation of the Warriors. His combination of athleticism, defensive versatility, and growing offensive skillset makes him a prime candidate for a breakout season if given a larger role.

JONTHAN KUMINGA THROWS IT DOWN🔨

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For the Bulls, Kuminga would immediately address their most glaring weakness: wing depth and scoring at the forward position. While Buzelis is projected to become that player in the long run, the Bulls cannot expect a young prospect to shoulder the responsibility of guarding All-Star forwards and producing 15+ points per night. Kuminga, with his explosive athleticism and ability to create off the dribble, could provide that bridge between the present and the future.

Defensively, pairing Kuminga with Okoro would give the Bulls one of the most disruptive perimeter duos in the Eastern Conference. That type of defensive presence is the exact formula Chicago has been missing in their failed playoff pushes over the last several years. Offensively, Kuminga thrives in transition and could greatly benefit from Giddey’s passing vision.

Imagine Giddey pushing the ball up the floor with Kuminga filling the lane and Buzelis trailing for spot-up threes. It’s the type of young, athletic lineup that could finally bring life back to the United Center.

Anfernee Simons: The offensive sparkplug Chicago has missed

While Josh Giddey provides playmaking and Coby White offers scoring bursts, the Bulls are still in need of a true dynamic guard who can create his own shot consistently against playoff defenses. That’s where Anfernee Simons of the Boston Celtics comes into play. Simons, now entering his prime, has proven himself to be one of the league’s most explosive scorers. His three-level scoring ability, particularly from beyond the arc, would give the Bulls an offensive weapon they haven’t had since the days of Zach LaVine.

Anfernee Simons – Career Passing Highlights https://t.co/e49oHNw8DM pic.twitter.com/vMs203GBOl

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For Chicago, Simons would slide seamlessly into the starting backcourt next to Giddey, balancing out his pass-first tendencies with a guard who thrives as a shot creator. Simons averaged over 19 points per game in Portland before being traded to Boston despite defenses keying in on him, and in Chicago, he would benefit from the spacing created by Vucevic’s shooting and the drive-and-kick opportunities from Giddey. The Bulls’ half-court offense, which has often stagnated in recent seasons, would suddenly have a player capable of breaking down defenses at will.

The appeal of Simons goes beyond scoring. He’s still only 26 years old, meaning he fits the Bulls’ timeline perfectly. With Buzelis and Giddey both still in development phases, Simons’ presence could alleviate some of the offensive pressure on them and allow them to grow without being forced into uncomfortable roles too early.

Walker Kessler: The rim protector who could anchor Chicago’s defense

The final piece of the puzzle for the Bulls may not be on the perimeter at all, but rather in the paint. Nikola Vucevic has been a steady presence offensively, but his defensive shortcomings have long been an issue for Chicago. That’s where Walker Kessler of the Utah Jazz enters the conversation. Kessler, one of the league’s premier young shot-blockers, could provide the defensive anchor the Bulls have been missing for nearly a decade.

Walker Kessler Defense on Jokić

Jokić shot 40% FG when Kessler was his primary defender (2024-25) pic.twitter.com/IbaKMPek5D

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At just 24 years old, Kessler already possesses elite rim-protection instincts and rebounding ability. His defensive metrics place him among the top young centers in the NBA, and his presence would instantly elevate Chicago’s interior defense. With Kessler patrolling the paint, the Bulls’ perimeter defenders could play more aggressively, knowing they have a reliable shot-blocker behind them. It’s a dynamic that championship-level teams have leaned on for years, and Chicago has an opportunity to replicate it.

Offensively, Kessler’s role would be far simpler but still impactful. He’s not a floor-spacer like Vucevic, but he’s an efficient finisher around the rim, thriving as a lob target and offensive rebounder. With Giddey’s ability to orchestrate pick-and-rolls, Kessler could find easy scoring opportunities without needing plays called for him.

This balance of rim protection and opportunistic scoring is exactly the kind of role player Chicago has lacked, and pairing Kessler with Vucevic could also allow the Bulls to experiment with different frontcourt combinations depending on matchups.

The Jazz, meanwhile, are still in a transitional phase and could be open to moving Kessler for the right package. For Chicago, this would not only be an investment in the present but also in the future, as Kessler has the potential to be a defensive cornerstone for the next decade.

Where do the Bulls stand in the East?

The Chicago Bulls enter the 2025-26 season with optimism, momentum, and a real opportunity to break their long playoff drought. Their offseason moves were strong, but in a wide-open Eastern Conference, the difference between another play-in disappointment and a playoff breakthrough could come down to a single bold trade.

Jonathan Kuminga could provide the two-way wing depth they desperately need. Anfernee Simons could give them the scoring firepower to compete with the East’s elite guards. Walker Kessler could anchor the defense and bring stability to the paint.

Whether they ultimately pursue one of these names or another, one thing is clear: the Bulls cannot afford to sit idly by this season. Their time to make a move has come, and if they strike the right deal, Chicago basketball could finally return to the postseason spotlight.