Chicago Bears are more prepared for Caleb Williams than they were for Justin Fields

The Chicago Bears are known as the franchise where quarterbacks go to die. The list of Chicago’s failed starters is long, and it includes first-round picks, high-paid free agents, and veterans acquired by trade. But it feels like that’s about to change with Caleb Williams, the presumptive first pick in the 2024 NFL Draft.

Sure, the pessimist will say we’ve been here before, that guys like Cade McNown, Rex Grossman, and Mitch Trubisky were supposed to break the curse, too. Most recently, it was Justin Fields, whom the Chicago Bears gave away to the Pittsburgh Steelers for a conditional sixth-round pick in the 2025 NFL Draft.

Why should we expect anything different from Williams? What makes this time the right time?

Unlike some of the situations those other quarterbacks were dealt in Chicago, Williams is joining a Bears team that’s ready to win… now. They finished the final eight games of the 2023 season, led by a strong defense, with a 5-3 record. General manager Ryan Poles has balanced the roster with big-name offensive weapons like Keenan Allen and D’Andre Swift this offseason. Simply put, this Bears team is different.

MORE: Here’s proof that the Chicago Bears won QB lottery in 2024 NFL Draft

Here’s another point to consider: Caleb Williams experienced a worst-case scenario during his final season at USC. His supporting cast wasn’t strong, and the Trojans’ defense was one of the worst in the country. And he still enjoyed success. He’ll experience a sense of relief as a rookie, knowing he doesn’t have to play hero ball every time the Bears are on offense; he can count on guys like Montez Sweat and Jaylon Johnson to do their jobs.

Compare Williams’ upcoming experience with the Bears to what Justin Fields endured. Fields played behind a patchwork offensive line and threw to receivers (before DJ Moore’s arrival in 2023) whose resumes were barely worthy of an NFL roster. His receivers included a checked-out Allen Robinson and guys like Rodney Adams and Damiere Byrd.

Who?! Exactly. Fields was forced to run for his life, and as a result, he nearly broke the single-season rushing record for a quarterback in 2022. 

But Justin Fields’ style of play isn’t a sustainable model for success. Caleb Williams’ is. And his weapons are very different: Moore, Keenan Allen, a likely rookie top-10 receiver (or offensive lineman!), and D’Andre Swift. It’s a Who’s Who of skill players in the NFC. It’s almost too good to fail.

So, yeah, expectations around Williams will naturally be high because of his status as the first overall pick. And the pressure to meet them will be higher because of the city he’s playing in. But unlike the Chicago Bears quarterbacks who’ve failed before him, Caleb Williams is set up for success. Now, it’s up to him to achieve it.

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