​LAKE FOREST, ILLINOIS – JULY 29: Caleb Williams #18 of the Chicago Bears speaks to the media during Chicago Bears Training Camp at Halas Hall on July 29, 2026 in Lake Forest, Illinois. (Photo by Geoff Stellfox/Getty Images) | Getty Images Alright, let’s lock into a contract extension that I think most Bears fans are curious about: Caleb Williams.We’ve been looking at several key veterans across the Bears roster and whether the Bears, in the next 12 months, should extend them (Cash), cut them (Slash), or wait a year and make a determination (Slash).This one is easy; it’s the details that are trickier.Caleb Williams: CashThere’s no reason to spend a lot of time discussing why Caleb should be extended. He has the late-game heroics, the generational talent, the relationship with Ben Johnson, the huge leap from year one to year two, he’s only getting better and we’ve seen the players (NFL Network’s Top 100) ranked him as the 10th best QB, Jeremy Fowler’s poll ranked him as the 10th best QB, and Mike Sando’s QB Tiers ranked him as the 11th best QB.After two seasons, Caleb Williams has cracked the top 10 QBs in the NFL by everyone across the league. He has a chance to be pushing to be a top 5 QB by the end of this season. He will easily be the best QB in Bears history when it’s all said and done (Sorry, Sid Luckman, your 80-year reign at the top is over). You don’t mess around when you have a talent like Caleb Williams. You pay him.So what kind of contract are we looking at for Caleb? It’s going to be expensive.This is going to be the largest contract the Bears have ever given out, and it’s not even going to be close. In fact, I will go out on a limb and say that this contract will double the largest contract the Bears have ever handed out (which the honor now belongs to Darnell Wright).When you look at the highest-paid QBs in the NFL, there is a collection of QBs that are making $55 million per season (Joe Burrow, Josh Allen, Jordan Love, Trevor Lawrence, Matthew Stafford). That’s where the negotiation begins. There’s no chance that Caleb would accept less than $55 million per season, and I think he’s going to clear that.There are only two QBs that make above that $55 million threshold. Dak Prescott, who makes $60 million per season, and Patrick Mahomes, who sits at $64 million per season. It should be noted that both Prescott and Mahomes are on their third contract and not their second contract, which obviously is a little different than the position where Caleb will be negotiating from.I also think it’s worth noting that I think Caleb is going to drive a hard bargain. I think down the line, we may see Caleb taking discounts so the Bears can sign more players, but I think for contract number two, Caleb is going to be looking to break the bank. I think he’s going to ask to be the highest-paid QB in the NFL. I don’t think he necessarily will get it. But I think, if the Bears start at $55 million per season, I think