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

As the 2025 NFL trade deadline approaches, Ryan Poles will need to make smarter moves than he has in the past.

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The Chicago Bears find themselves at an intriguing crossroads as the 2025 NFL trade deadline approaches (Nov. 4 at 4pm EST). They currently stand at 4-3 with a favorable schedule over the next month and reason to believe that their best football is ahead of them. If that's the case, general manager Ryan Poles needs to strongly consider making a move for one of a handful of top trade targets for the Bears. The squad still has several roster needs due to injuries this season, even after signing a former nemesis in C.J. Gardner-Johnson.

However, Poles' track record for making deals at the deadline isn't exactly stellar. He's made some pretty bad trades, but these three in particular stand out among the rest.

3. Ryan Bates - 2024 offseason trade

While this trade wasn't the kind of bust that could endanger a GM's job, it just never made any sense. Poles had tried and failed to sign Bates as a restricted free agent in the past, and it felt like he was forcing the issue here. Bates had always been a backup in Buffalo, so I'm not sure why Poles thought he was the missing key to unlocking a better offensive line.

At the end of the day, this one only cost Chicago a fifth-round pick in 2024, but Poles has actually done pretty well with fifth-round picks in the past.

Grade: C-

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2. Montez Sweat - 2023 trade deadline

After the Bears traded for Montez Sweat at the 2023 deadline, he finished the season as a Pro Bowler and looked like an instant hit, but his performance in 2024 was a steep drop off and 2025 started off as more of the same. To his credit, he has three sacks and two forced fumbles in his last five games, which could be the signal of a turnaround, but Sweat is simply not playing anywhere close to the standard of his hefty $98 million contract.

We also have to consider Chicago's missed opportunity resulting from this trade. Bringing Sweat over from Washington cost the Bears what ended up being the 40th overall pick in the 2024 NFL draft, which was used by the Eagles to select defensive back Cooper DeJean. Ouch.

Grade: D+

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1. Chase Claypool - 2022 trade deadline

I think every Bears fan knew what was coming here, but I'll start with a disclaimer: I liked the process that led to this trade. Claypool had shown flashes of an All-Pro receiver as a rookie, was a rare athlete with a huge frame, and Chicago desperately needed wide receiver help at the time. So I get why Poles made the move to acquire Chase Claypool from the Steelers.

Regardless, this one backfired spectacularly. Claypool played in just ten games for Chicago, catching 18 passes and one, single touchdown, before being traded in 2023 to the Dolphins for a Day 3 pick-swap in 2025. Frankly, it's a miracle that Poles was able to get anything in return after how bad Claypool looked in Chicago.

As with the Sweat trade, we must also consider Chicago's missed opportunity in the 2023 NFL draft. They sent the steelers what ended up being the first selection of Round 2, which they used to draft cornerback Joey Porter Jr, who the Bears could desperately use right now. No two ways about it, this trade was a complete disaster.

Grade: What comes below an F-?

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