The Chicago Bulls are in the midst of one of the most pivotal offseasons in recent franchise history. After parting ways with key front-office figures and seeing head coach Billy Donovan step away, the organization is undergoing a comprehensive rebuild of its basketball operations. As the search intensifies for new leadership, a veteran insider has delivered a bold, betting-man’s prediction that could signal exactly where Chicago is headed.
Veteran Chicago Bulls reporter Joe Cowley, responding to fan questions on social media, didn’t mince words. When asked about his top picks for the team’s next general manager, Cowley laid it out plainly: “If I was a betting man I would put whale money on (Matt) Lloyd, and a small side bet on (Dave) Lewin also included if the odds were right.”
This isn’t idle speculation. Cowley’s track record and deep sourcing within the organization lend significant weight to his assessment. In NBA circles, when a plugged-in insider like Cowley goes “all-in” on specific names, the league takes notice.
Why Matt Lloyd Tops the List
Matt Lloyd, currently the General Manager of the Minnesota Timberwolves, emerges as the clear frontrunner according to Cowley. Lloyd has served as Tim Connelly’s right-hand man, playing a pivotal role in building Minnesota into a perennial contender that has reached the Western Conference Finals in back-to-back seasons.
His experience constructing a winning roster in a competitive Western Conference makes him an attractive target. Poaching talent from a successful franchise like the Timberwolves is a proven strategy, and Lloyd’s background—including prior time in the Bulls’ organization—adds familiarity with Chicago’s market and culture. If hired, his analytical approach and player-development focus could provide the fresh perspective the Bulls desperately need.
The Dave Lewin Upside Play
As the “small side bet,” Cowley highlights Dave Lewin, Assistant General Manager of the Boston Celtics. The Celtics have been a model of sustained excellence over the past decade, and Lewin has contributed to their front-office success. Even in a transitional season with Jayson Tatum sidelined, Boston exceeded expectations by winning well over 50 games.
Lewin represents the kind of steady, championship-proven executive who could help the Bulls navigate free agency and future drafts with discipline and vision.
The Broader Context: Rebuilding with Urgency
The Bulls missed the postseason for the first time in five years during the 2025-26 season, creating both pressure and opportunity. With cap space available this offseason and key roster decisions looming, the new front-office leadership will immediately face critical choices about the team’s direction—whether to push for contention or lean further into a youth-focused rebuild.
Michael Reinsdorf and the Bulls’ ownership understand the stakes. The organization has already begun interviewing candidates and moving swiftly to fill these vacancies. Cowley’s prediction suggests the shortlist is not only secret but highly targeted toward proven executives from winning programs.
What This Means for the League
If Cowley’s “gambler’s lock” hits, the Bulls could shock the league by injecting high-level, externally validated talent into their front office. Lloyd or Lewin would bring immediate credibility and a blueprint for success that Chicago has lacked in recent cycles. The ripple effects would be felt across the NBA, as teams like Minnesota and Boston defend against further poaching while the Bulls reposition themselves as a destination for top executive talent.
For now, all eyes remain on Chicago. As the search narrows, one thing is clear: the veteran insider has placed his bets, and the basketball world is watching to see if the Bulls cash in. The next chapter of Bulls basketball may be defined not just by who they hire, but by how decisively they act on recommendations like Cowley’s.