Bear Digest

Grading Ryan Poles' best trades as Chicago Bears GM as NFL trade deadline looms

Without these trades, the Chicago Bears as we know them would be in a much worse spot.
Pete Martuneac|
David Banks-Imagn Images

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Chicago Bears general manager caught a lot of flak from the fans when the Bears signed him to a contract extension through 2029, and it's hard to blame them. Under Poles' watch, the Bears have won just 15 games across three complete seasons. He's also been the architect of some of the worst trades as the Chicago Bears GM.

However, there remains plenty of reason for optimism, thanks in large part to a handful of excellent deals made by Ryan Poles. Yes, he's bungled a few trades that cost the Bears dearly, but he's also hit some absolute home runs, too.

With the 2025 NFL trade deadline looming, let's review Poles' three best trades.

3. Khalil Mack - 2022 offseason

Poles' first move as GM of the Chicago Bears was a big one, and it signaled that the Bears were heading into a new era. Acquiring Khalil Mack trade in 2018 was one of the biggest trades in Bears history, but it never quite worked out for the team and by 2022 Mack was no longer the dominant game-wrecker he'd once been.

Trading Khalil Mack to the Chargers was the right move, and Poles got a pretty decent return: a second-round pick in 2022 that became Jaquan Brisker, and sixth-round pick, also in 2023. Fast-forward three years and Brisker appears to be a key piece of this defense (when healthy) while Mack's level of play has continued to decline.

Grade: B+

Khalil Mac
Milwaukee Journal Sentinel-Imagn Images

2. Joe Thuney - 2025 offseason

After largely neglecting the offensive line through is first three offseasons, Poles threw everything plus the kitchen sink into this unit in 2025. Jonah Jackson and Drew Dalman were good acquisitions, but the big fish was landing four-time All-Pro guard Joe Thuney from the Chiefs for nothing more than a 2026 fourth-round pick. That's a future Hall of Fame offensive lineman for what is essentially a dart throw at the end of the draft.

Thuney has been transformative for Chicago's O-line. He's been called for just one penalty, and even that was questionable, while surrendering zero sacks and earning an elite 82.9 pass blocking grade from PFF. The four-time Super Bowl champion is a steadying presence along the O-line, improving his linemates and helping Caleb Williams develop into a franchise quarterback.

The best part of this deal? The Bears and Joe Thuney already agreed to a 2-year contract extension, keeping him in Chicago through 2027.

Grade: A

Joe Thune
David Banks-Imagn Images

1. First-overall selection in the 2023 NFL Draft

Call it luck if you want, but Ryan Poles authored arguably the most impactful trade in Chicago Bears history when he dealt the first-overall selection in the 2023 NFL Draft to the Carolina Panthers. Chicago received a king's ransom to move down eight spots in the draft, in addition to a 2024 first-round pick, a 2025 second-round pick, and wide receiver DJ Moore.

A hefty price if ever there was one, but it only got sweeter when that 2024 first-round pick became the first-overall pick, which the Bears used to select Caleb Williams.

By the time the dust settled on this trade and all the exchanged picks had been used, it ended up being one of the most lop-sided deals in NFL history, especially with Carolina quarterback Bryce Young on the verge of playing his way into a backup role. On the other hand, Williams looks the part of a franchise quarterback while the Bears used those other picks to acquire players who look to be franchise cornerstones in their own right.

Again, you can call this pure luck for Ryan Poles, and you'd have a point. It took the Houston Texans authoring a miraculous Week 18 comeback victory over the Indianapolis Colts to secure that first-overall pick for Chicago, but as the old saying goes, it's better to be lucky than to be good.

Grade: A+++

Caleb William
Kirby Lee-Imagn Images

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Pete Martuneac
PETE MARTUNEAC

A former Marine and Purdue Boilermaker, Pete has been covering the Chicago Bears since 2022 as a senior contributor on BearsTalk. He lives with his wife, two kids and loyal dog.

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