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ChiCitySports
Home » Chicago Bulls » This is the Chicago Bulls biggest question they need to answer
Chicago Bulls

This is the Chicago Bulls biggest question they need to answer

Vincent PensabeneBy Vincent PensabeneMarch 23, 20262 Mins Read
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Dec 3, 2025; Chicago, Illinois, USA; Chicago Bulls head coach Billy Donovan directs the team during the first half against the Brooklyn Nets at the United Center. Mandatory Credit: Matt Marton-Imagn Images
Dec 3, 2025; Chicago, Illinois, USA; Chicago Bulls head coach Billy Donovan directs the team during the first half against the Brooklyn Nets at the United Center. Mandatory Credit: Matt Marton-Imagn Images
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The Chicago Bulls pulled the switch at the NBA Trade Deadline this year and sold off players. However, this created a question regarding the team’s future in a different way. They now have to decide which players they want to keep and which to let leave the organization. There are some pressing questions the front office has to find answers for, but what is the biggest question right now?

The Chicago Bulls need to figure out which guards they are going to keep

Chicago Bulls guard Collin Sexton (2)
Chicago Bulls guard Collin Sexton (2) shoots the ball against the Brooklyn Nets. Mandatory Credit: Vincent Carchietta-Imagn Images

Bleacher Report’s Zach Buckley wrote an article discussing each NBA team’s biggest question they need to answer. For the Bulls, it was figuring out which guards they would keep. Below is what Buckley wrote:

“It took the Bulls way too long to pull the plug on their last core, but at least they held nothing back once they finally did. They sent most recognizable faces packing and replaced them with a pile of second-round picks and a number of new players. But, uh, why are so many of the newbies guards?

“Collin Sexton, Jaden Ivey, Anfernee Simons and Rob Dillingham collectively crowded the backcourt upon their arrival. Only so many can be part of the long-term plans, and honestly, at least a few won’t even be a part of the near-future plans, as Dillingham is the only member of that quartet not ticketed for free agency after this season.

“So, clearly they aren’t all keepers, but you’d presume at least a couple are or could be held in that regard, right? Is it as simple as keeping the two youngest, Ivey (a restricted free agent if he gets a qualifying offer) and Dillingham (who could have two more seasons on his rookie deal)? Or is there a chance for Sexton and/or Simons to play their way up the pecking order?”

Chicago can let one or two of these guards go this offseason and still have a young core of backcourt players to pair with Josh Giddey. It will be interesting to see who the front office wants to keep going into next season.

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BY Vincent Pensabene

Vincent Pensabene is a trending news writer for ChiCitySports.

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