Dan Orlovsky evaluates how Chicago Bears OC hire Shane Waldron affects potential No. 1 pick Caleb Williams

The Chicago Bears had two big questions entering the offseason after opting to keep head coach Matt Eberflus. The first was at offensive coordinator, and that answer came Monday when the franchise hired Shane Waldron to replace Luke Getsy.

Now, the Bears have to figure out the more important issue they’re facing this offseason. Should they move on from Justin Fields and draft Caleb Williams with the No. 1 overall pick, or keep Fields and trade the selection for a huge haul?

To ESPN’s Dan Orlovsky, it’s trending toward the former. In fact, Waldron’s hiring could have a long-term effect if the Bears wind up drafting Williams considering his history with another former No. 1 overall pick: Jared Goff.

“Ever since this season’s ended, I kind of started to lean that way that Chicago was going to trade [Fields] and go get Caleb Williams,” Orlovsky said on NFL Live. “Shane Waldron getting hired as their offensive coordinator, I was with him with the Rams. He got to watch the development of a young Jared Goff. He was there to watch how Matt LaFleur, when he was there with Jared, developed him and helped him and as Zac Taylor developed him when it comes to that young quarterback. So I do like the fact that he’s watched that.”

No matter where Williams ends up — whether it be Chicago or elsewhere — Orlovsky said he’ll have to learn how to settle in to a scheme. He showcased his ability to improvise and make plays on the fly while at USC, but fitting into an offensive structure will be crucial to his success in the NFL.

“I think the No. 1 challenge is going to be getting [Williams] to develop within the rhythm and timing of an offense,” Orlovsky said. “It is going to be necessary for every quarterback to live in that world. Playmaking, not a problem. Getting him to that, that is going to be the biggest development of his young career.”

ESPN’s Mel Kiper Jr.: Chicago Bears facing plenty of unknowns with Justin Fields, Caleb Williams

In his Mock Draft 1.0, ESPN’s Mel Kiper Jr. projected the Bears to trade Fields and draft Williams with the No. 1 overall selection, which they received from the Carolina Panthers as a result of last year’s trade. It’s not a cut-and-dry decision, though. Fields showed promise as the 2023 season went along, both with his arm and his legs, and it’s making for quite a call for Ryan Poles and the Chicago front office.

Even Kiper admitted it’s not going to be easy.

“Talk about resetting the clock. Mike Tannenbaum talks about that all the time. If it’s even, you take Caleb. Unless Justin Fields is significantly better in your mind right now where he is, then roll the dice on Caleb. People say it’s an unknown on Caleb. Well, it’s an unknown on Justin whether he can be a franchise quarterback,” Kiper said.

“So, I would trade Justin Fields, try to recoup that second round pick you lost with the Montez Sweat trade, which was a great trade, Montez Sweat is a heck of a player, and then you get a fourth round pick, a two and a four, two and a three. Bottom line is trading Justin Fields makes the most sense. Taking Caleb Williams has the chance to be, I’m not gonna say generational because I said it with [Trevor] Lawrence and Lawrence hasn’t gotten there yet, but he could be one of the top five quarterbacks in the NFL. That’s what you’re hoping for. That’s why you take him No. 1 overall.”