It was Oct. 14 in South Bend, Ind., and Chicago Bears GM Ryan Poles was working the sideline as he normally would at a college game in the fall—looking, with a scout’s eye, for any little window he could find into the prospects he’d be evaluating in the winter and spring.
The USC offense was wrapping up warmups. The punt team was coming on. The Trojans’ reigning Heisman-winning quarterback, Caleb Williams, had looked over to the Irish sideline earlier, and spotted Notre Dame icon, and NFL legend, Joe Montana. Sensing the timing was right, he put his head down and went.
Poles watched intently.
Williams was born in November 2001, nearly seven years after Montana played his last game. Some of his contemporaries wouldn’t even know who Montana was, let alone recognize him in street clothes. But here was Williams, preparing for his final shot at Notre Dame as USC quarterback, compelled to pay homage to one of the game’s greats.
“They went to do some special teams things, he took his helmet off, ran over and shook his hand,” Poles said Thursday. “For a young kid to go up to a quarterback like that, Hall of Famer, and not as an, , but , and, yet, there wasn’t this college fear of talking to an adult. He did it with confidence and swagger, but a ton of respect and humility at the same time—I couldn’t get that out of my mind.”
At the time, there was no way for Poles to know he’d have a prayer of landing Williams in the draft.
Sure, he had two first-round picks, and with the Bears’ record at 1–4 and the Carolina Panthers’ 0–5, there was a good chance both would be in the top 10. Still, he and his coach, Matt Eberflus, were headlong in the process of evaluating Justin Fields, coming off one of his best games as a pro, a four-touchdown effort in a win over the Washington Commanders, and it was pretty well-established by then that only one NFL team would have a shot at USC’s quarterback. There was also a lot of season left to be played.
So Poles filed the memory away, an early step he’d take in executing the Bears’ aggressive, forward-thinking plan to both give Fields a shot and be prepared for whatever opportunity Chicago’s draft position afforded him at the position.
This week, we’re going to take you, soup to nuts, through that plan, and how it got Poles and Eberflus to the point where they were ready to trade Fields and tie their job security to a guy who’s been tagged a generational talent at the position since he was a teenager. And what you’ll see is that just as that sort of big-picture view of the quarterback was important, so too were all the little details along the way.
Even if it was just that short interaction before the worst game of Williams’s college career.






