Chicago Bulls or Chicago Fools?
It’s been nothing short of a rollercoaster for Bulls fans over the past decade. From the highs of the Derrick Rose–Joakim Noah era, when Chicago was clawing at the door of contention for several years, to the crushing blow of injuries that derailed that core. Then came the dismantling of the Rose–Butler era, followed by years of rebuilding and searching for direction.
There was a flicker of hope with the Ball–LaVine–DeRozan–Vucevic group, a lineup that briefly looked like it could restore excitement in Chicago. But with injuries, inconsistencies, and an unclear long-term vision, that spark faded.
Now, the Bulls find themselves in a familiar place: directionless, stuck rebuilding, with no clear path forward.
In 2021–22, the Bulls didn’t just return to respectability — they stormed into the East as frontrunners, controlling the conference and flashing the look of a genuine contender.
Unfortunately, Lonzo Ball suffered a partial tear in his left meniscus. What was initially projected as a routine six-to-eight week recovery spiraled into an infamous two-year absence from the NBA. Ball’s absence quickly revealed how irreplaceable he truly was to Chicago’s identity. Believing his return was only a matter of time, the Bulls chose patience, holding onto Ball in hopes that the same team that once started 27–13 with a healthy Ball would eventually reclaim its success.
While Lonzo’s injury is the main contributor as to why the Bulls could never find success on the court, the true tragedy lies with the front office mismanaging their assets which has resulted in the team as we know it today.
The timing of Zach LaVine’s five-year, $215 million extension in 2022 was questionable at best. At the time, LaVine had already shown durability concerns with recurring knee issues, and while he was an All-Star talent, his fit as a franchise cornerstone was one to be skeptical of. Instead of exploring the trade market when his value was at its peak, the Bulls locked themselves into a long-term, max-level deal. Just a year later, LaVine’s contract was viewed as one of the least movable in basketball. As of today, Zach LaVine suits up for the Sacramento Kings, dealt away as part of a midseason three-team blockbuster that sent De’Aaron Fox to the Spurs. For Chicago, the return was underwhelming to say the least. They brought back two average players saddled with bloated contracts, a serviceable point guard in Tre Jones, and — perhaps the most ironic piece — their own 2025 first-round pick. For a player who once represented the Bulls’ future and was handed a max extension to be the face of the franchise, this is a stunningly poor return.
What made the LaVine extension look even more foolish in hindsight was how the Bulls handled his running mate, DeMar DeRozan. His arrival in 2021 was supposed to mark Chicago’s return to relevance — and to DeRozan’s credit, he delivered, putting together two All-NBA caliber seasons and some of the best individual stretches of his career. But the front office paid dearly to get him, sending San Antonio a first-round pick, Thaddeus Young, and other assets in a sign-and-trade. Instead of recognizing the ceiling of the roster and flipping DeRozan while his value was high, Chicago clung on. By the time reality set in, his market had cooled. At 35 years old, DeRozan walked out the door in another sign-and-trade, this time to Sacramento, netting the Bulls two second-round picks and a player who is already out of the league. For a consistent 20+ point-per-game scorer, that return is meager — especially for a team desperate for youth and draft capital. Even if DeRozan’s game wasn’t a perfect fit for Chicago’s long-term vision, turning a former All-NBA wing into essentially a second-round pick and cash only reinforced the franchise’s chronic inability to maximize its assets.
Perhaps the most damning move of all was trading Alex Caruso. He wasn’t just an elite defensive presence — he was arguably the Bulls’ most valuable player, the connective tissue who elevated everyone else on the floor. More importantly, he was one of the few assets on the roster with consistent league-wide interest, the type of player contenders would overpay to acquire.
And yet, the Bulls failed to maximize him. Instead of extracting a first-round pick, which should have been the baseline price for a player of his caliber, Chicago settled for Josh Giddey. While Giddey is undeniably talented — a 6’6” guard with great playmaking ability — the deal underscored the Bulls’ lack of leverage and foresight. To trade with the Oklahoma City Thunder, an organization sitting on a historic stockpile of first-round picks, and not secure even one in return is frankly embarrassing.
What makes this move look even worse in hindsight is the contrast in outcomes. Caruso became one of the driving forces behind the Thunder’s championship run, validating every bit of the league-wide interest he had generated. Meanwhile, the Bulls now find themselves in a precarious position, struggling to agree on a long-term deal with Giddey. If they can’t reach an extension, they could lose him outright in unrestricted free agency after next season. In other words, Chicago managed to turn their most valuable asset into a two-year rental — and strengthened a contender in the process.
The Bulls have repeatedly failed to extract meaningful returns from their top assets, but their handling of Nikola Vučević might be their worst work. After trading two first-round picks — one of which became Franz Wagner — to acquire him in 2021, the front office clung to Vučević out of stubborn loyalty and a refusal to admit the trade was a mistake. Instead of flipping him when his value was still respectable, either at the trade deadline or during seasons where playoff contention was already slipping away, Chicago doubled down.
They justified the sunk cost, holding on year after year until eventually re-signing Vučević to a three-year extension. The result? Seasons of middling production that never elevated the franchise, while the opportunity to recoup value slipped away entirely.Now, the Bulls have finally reached their breaking point. Reports indicate they are actively searching for a trade suitor for Vučević, but unsurprisingly, there’s virtually no market for a soon-to-be 35-year-old center with declining athleticism and a hefty contract. The writing is on the wall: whether through trade or buyout, Vučević will not be on the roster by the start of next season.
The Bulls may walk away with absolutely nothing for a player who once made multiple All-Star teams and cost the franchise two first-round picks. What already felt like a long shot of a trade at the time now looks, as the dust settles, like a complete failure. If Vučević exits without bringing back even a marginal return, it would cement him as the centerpiece of a lopsided move in recent NBA history.
Across all these moves, a clear pattern emerges: the Bulls held onto assets too long, consistently misjudged timing, and failed to replenish their draft capital. Despite having multiple opportunities to reset or retool, Chicago never secured a single first-round pick that wasn’t their own for LaVine, Vučević, DeRozan, or Caruso. Instead of charting a new course, the front office clung to a vision that never materialized, leaving the franchise in limbo — neither a contender nor a true rebuilder.
