The Chicago Bulls’ offseason moves have crystallized a troubling pattern that extends far beyond individual transactions. What began as championship pedigree has devolved into a franchise operating without coherent direction, leaving fans and analysts questioning whether management understands the path forward.
The Bulls’ recent trading spree — moving Zach LaVine, DeMar DeRozan, Alex Caruso, and Lonzo Ball while securing just one first-round pick in return — represents more than poor asset management. It signals a franchise caught between competing philosophies, unable to commit fully to rebuilding or contending.
Bill Simmons Exposes the Bulls’ Strategic Confusion
Bill Simmons has emerged as one of the Bulls’ harshest critics, and his latest assessment cuts to the heart of Chicago’s dysfunction. His frustration with the franchise traces back to early February when the Bulls’ trade deadline moves revealed a front office seemingly operating without a master plan.
The LaVine trade to Sacramento exemplified this confusion. In a three-team deal, the Bulls received Zach Collins, Tre Jones, Kevin Huerter, and a protected 2025 first-round pick — except that pick turned out to be their own, previously traded to San Antonio. The return failed to address Chicago’s long-term needs while adding salary commitments that complicated future flexibility.
Caruso’s departure to Oklahoma City for Josh Giddey represented another puzzling decision. While Giddey brings youth and playmaking, trading away one of the league’s premier perimeter defenders for a player who doesn’t address the Bulls’ spacing issues highlighted the franchise’s inability to identify its core identity.
DeRozan’s trade to Sacramento for Chris Duarte, two second-round picks, and cash considerations completed the Bulls’ veteran exodus. The lack of first-round compensation for a player of DeRozan’s caliber underscored Chicago’s weak negotiating position and poor timing in the marketplace.
Simmons didn’t hold back in his assessment, saying, “They have an absentee landlord as an owner.”
The Broken AI Engine Theory Reveals Deeper Problems
Simmons’ latest criticism cuts deeper than individual trades, targeting the Bulls’ fundamental approach to roster construction. He said, “Chicago feels like they’re being run by an AI engine that broke. And the only thing they put in was: we don’t want to pay the luxury tax. Could you suggest some moves for us? Yes. And the engine was like, trade Lonzo Ball for Isaac Okoro, even though you already have Patrick Williams.”
Bill Simmons roasting the Bulls pic.twitter.com/gYZ4AjDvdb
— Die-Hard Chicago Bulls Fans (@DieHardCBfans) July 4, 2025
The Ball trade perfectly illustrates Simmons’ point. Ball’s injury history — missing two full seasons and playing just 35 games in 2024-25 — made him a logical trade candidate. However, the Bulls reportedly rejected a superior offer earlier in the season that included a first-round pick, instead settling for Isaac Okoro from Cleveland.
Okoro’s arrival creates roster redundancy that suggests poor planning. The 6’5″ wing brings solid defense but limited offensive upside, duplicating Patrick Williams’s skill set. Without draft compensation to justify the move, the trade appears driven more by salary considerations than basketball strategy.
Even Chicago’s draft maneuvering drew criticism. Former Memphis Grizzlies executive John Hollinger wrote, “Chicago swapping pick 45 for the Lakers’ pick at 55 and cash is another reminder that the Bulls are an unserious franchise.”
The Bulls’ current negotiations with Giddey, who averaged 14.5 points last season, face an asking price of around $30 million. Whether Chicago commits to that investment will reveal whether the franchise has learned from its recent missteps or continues operating without clear direction.