After the 2026 season, Chicago Bears quarterback Caleb Williams will be eligible for his first extension with the team that drafted him first overall and it could be a massive one, like potentially record-breaking.

Bears general manager Ryan Poles, earlier this offseason, said that the Bears have already started ironing out what that extension will look like with Williams and how his new deal will impact the rest of the roster from a financial standpoint.

The quarterback market took a substantial jump earlier this offseason when Patrick Mahomes added two years to his deal with the Kansas City Chiefs, bumping his annual salary to a record-setting $64 million per year starting in 2027. That could easy set the bar for Williams to exceed the $60 million per year mark on his new deal. However, Williams’ approach from a money perspective could help out the Bears in a big way and it’s similar to the approach Tom Brady had throughout his career.

Caleb Williams is taking a similar approach Tom Brady had looking had to his future in Chicago

If Williams takes another leap in 2026 and leads this team to another deep playoff run, he absolutely would be worth that kind of money. But, from Williams’ perspective, it’s not all about the money to him when looking ahead to this future extension.

“I’ve been in the money phase of life for a good portion of my life now, since I was younger than most when you start earning money,” Williams said, via Hoge and Jahns. “So, money’s not a motivating factor for me in that sense. If I wanted to be done today, I’d be fine (financially)… That’s not my motivation.”

So, let’s actually break down what Williams is saying here. I think what he means is that money is not an issue to him. He’s already made millions of dollars, both in and out of football, for years now. He’s not motivated by being the highest-paid quarterback and loading up his bank account with the most money possible in his career.

We know what his motivations are. Williams wants to win. He wants to become the greatest of all-time. It’s the same mentality Tom Brady had and when it came to Brady’s contracts, he wasn’t worried about being the highest-paid quarterback of all-time.

Brady consistently took team-friendly deals with the New England Patriots so that the organization had the money to build the best possible team around him. Now, in 2010, Brady did sign the highest contract in NFL history (at the time). After that though, he gave the organization financial breaks to pay other players instead of being a top paid QB for roughly the next decade to hold that dynasty together for as long as possible.

“The most important thing is being able to make sure when I do get my contract that we can keep winning, that we can keep progressing as a team,” Williams said. “That’s my biggest goal when those moments do come up, when that time does come up, is how can this help us and propel us? Yes, it’s going to help me, but how can it keep us steady and be able to keep winning games, because that’s most important to me.”

Caleb Williams, however, plans to avoid making the one mistake Tom Brady did

As a result, it was Brady who went on to win six Super Bowls with the Patriots and another one with the Tampa Bay Buccaneers (on a two-year, $50 million deal). Brady still made his money and was one of the top earners in the NFL history. But, that didn’t matter to him. Those seven rings are all that mattered and that’s all that matters to Williams, too.

The only difference between Brady’s path to success and what Williams envisions for himself is the one decision Brady made late in his career: leaving New England.

“Stakes-wise, I obviously want to be here forever,” Williams added. “That’s a goal of mine when I made goals is to be at one place until I’m done. Until I decide that it’s over for me and I want to go home and ride off into the sun and things like that. I’m on a four-year contract with a possible fifth. I’ll be here. We’re going to keep winning games.”

This is the kind of approach Bears fans would love to hear from their franchise quarterback. Caleb Williams is a business-man first and understands the business of this league and what it takes to sustain success, as a team and individually. He also takes a lot of pride in being a Chicago Bear and spending his entire career with this organization.

How all of this comes together in regards to next year’s contract extension will be the key. But, by the sounds of it, I wouldn’t be shocked if Williams makes it a point to not be the highest-paid quarterback in NFL history like other top quarterbacks went out to achieve on their first extensions in previous years.