What was the Chicago Bulls' biggest regret in 2023?

Fans and experts alike have long been clamoring for the Chicago Bulls front office to green-light a rebuild. After a disappointing 2022-2023 season that saw them miss the NBA Playoffs, the writing on the wall was as clear as day: this current iteration of the Bulls isn’t good enough to be relevant.

Where did the Bulls go wrong? Bleacher Report’s Grant Hughes has an idea where the Bulls could have made a franchise-altering decision but didn’t.

Stuck in the middle

The middle is where NBA teams don’t want to be. It’s the purgatory of mediocrity, where a team is too good to land high draft picks but not good enough to make a deep run in the playoffs. The Bulls have been stuck in this middle ground for a few years now, and it’s all because the front office decided to stand pat at the 2023 NBA trade deadline.

Rather than let go of their high-priced players like Zach LaVine, DeMar DeRozan, and Nikola Vucevic, the Bulls doubled down on the roster, ardently believing the team had enough talent to make a playoff run. But as that season showed, Chicago didn’t have enough and fell short in the NBA Play-in Tournament.

“The 2023 trade deadline was Chicago's best opportunity to hop off its go-nowhere treadmill. Nikola Vucevic was ticketed for free agency, DeMar DeRozan would have been more than the partial-year rental he is now, and Zach LaVine, well...maybe his contract wouldn't have looked quite so cumbersome if the Bulls had dealt him when he was actually healthy,” Hughes wrote.