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5 Biggest Bulls mistakes that led up to the Caleb Wilson era

Here are the five biggest Chicago Bulls mistakes that all led to the Caleb Wilson era.
Nov 14, 2025; Chapel Hill, North Carolina, USA; North Carolina Tar Heels forward Caleb Wilson (8) reacts to a foul during the second half against the North Carolina Central Eagles at Dean E. Smith Center. Mandatory Credit: Scott Kinser-Imagn Images
Nov 14, 2025; Chapel Hill, North Carolina, USA; North Carolina Tar Heels forward Caleb Wilson (8) reacts to a foul during the second half against the North Carolina Central Eagles at Dean E. Smith Center. Mandatory Credit: Scott Kinser-Imagn Images | IMAGN IMAGES via Reuters Connect

It took a while for the Chicago Bulls to get to this point. The point where they actually have a guy who seems capable of leading them into the future: Caleb Wilson. It wasn’t always that way. For a while now, the Bulls didn’t really have a future to look forward to. Not enough to rebuild around.

The harsh reality is, for years, the Bulls were seemingly comfortable with living in the middle. They didn’t try hard enough to push forward, and they didn’t do anything to hit the reset button, get younger, and add high-potential assets. But now, they have Wilson. They have him and Matas Buzelis – two solid young pieces Chicago can build around.

But how did they get to this point? What bumps did they endure along the way? Here are five of the biggest mistakes the Bulls made, all of which led them to this current era of Chicago basketball.

5 Bulls mistakes that led up to the Caleb Wilson era

1. Nikola Vucevic trade

Hindsight is 20-20. The Bulls wanted to end their years of fruitless rebuilding, so they traded for Nikola Vucevic. Unfortunately, giving up multiple firsts for him was brutal.

Not having those picks seriously hurt the Bulls, especially when the core of Vucevic, Zach LaVine, and DeMar DeRozan. You just can’t give up picks like that.

2. Patrick Williams pick

This may be one of the worst picks in recent Bulls memory. Patrick Williams has not panned out for Chicago, and it doesn’t look like he will. He’s been brutal.

To make matters worse, Deni Avdija was selected five spots later. Tyrese Haliburton was at pick No. 12. Williams was No. 4. Four. Not a good selection, especially when picking that high.

3. Patrick Williams extension

Drafting a guy like Williams is one thing. Plenty of teams have made bad draft selections, even in the top five. But the Bulls made it worse when they decided to pay him.

Two summers ago, the Bulls signed Williams to a five-year, $90 million contract. That’s $18 million a season. A bad contract for a player who still hasn’t lived up to his billing.

4. Alex Caruso trade

Trading Alex Caruso was needed. The Bulls were smart to get some value back in return for him. But only getting Josh Giddey back and no picks wasn’t a good enough deal.

Giddey has been a solid player for Chicago, but he’s not exactly the type of guy the Bulls can easily build around. With his lack of shooting and defense, the Bulls would have been better off trying to land a first or two for Caruso instead.

5. Coby White trade

The Bulls waited too long. Coby White was a solid player for Chicago, and they could have tried to build around him a bit. But they didn’t. And then, they waited to trade him.

And rather than getting a first-rounder back, which they probably could have had a year or two ago, they only got second-rounders and Collin Sexton, who won’t be a part of the team moving forward.

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