The Chicago Bears shook things up in the NFL world with some bold trades. First, they swapped a 2025 sixth-round pick for Jonah Jackson from the Los Angeles Rams. Jackson had a tough season in LA, but the Bears hope to bring back his Detroit form. The next day, they made an even bigger splash by acquiring All-Pro guard Joe Thuney from the Kansas City Chiefs. This time, they gave up a 2026 fourth-round pick. Thuney is still a top player, but his age raises questions about how long he can keep performing at this level.

Ryan Poles, the Bears' general manager, has been busy. He's made around five trades a year since taking over. That's a lot by NFL standards. So, how has he done?

Let's start with the worst. Poles traded a 2023 second-round pick for wide receiver Chase Claypool from the Pittsburgh Steelers. Claypool didn't make a positive impact in Chicago and was eventually traded again. This move is likely to be remembered as Poles' biggest mistake.

Next up, Poles traded a 2024 sixth-round pick for offensive lineman Dan Feeney from the Miami Dolphins. Feeney had a nice mullet, but he only played 91 offensive snaps all season. Poles made this move in a panic due to uncertainty at the center position.

Poles also made a significant trade with the Baltimore Ravens. He acquired a 2023 second-round pick, a 2023 fifth-round pick, and linebacker A. J. Klein in exchange for Roquan Smith. Since leaving Chicago, Smith has been a first-team All-Pro and a top defensive player. The Bears traded him to sign Tremaine Edmunds, who hasn't lived up to his contract.

Poles also traded for wide receiver N'Keal Harry from the New England Patriots. He gave up a 2024 seventh-round pick, which wasn't much, and Harry didn't make a big impact in Chicago.

Poles traded for defensive lineman Chris Williams and a 2025 seventh-round pick from the Cleveland Browns. Williams played 367 snaps for the Bears last year and had some decent contributions. Poles made this move because Williams was likely to be released by the Browns.

Poles also traded quarterback Justin Fields to the Pittsburgh Steelers for a 2025 conditional sixth-round pick. Poles overplayed his hand and thought the market for Fields would be much more robust than it was. He used the media to push the narrative that the price would be a second-round pick, but no team was willing to come close.

Poles traded a 2024 fifth-round pick to the Buffalo Bills for offensive lineman Ryan Bates. Bates is on this list because he could still make the 2025 team and contribute in some capacity. As it stands right now, the Bears had to trade a 2025 fourth-round pick to get their pick back to draft Austin Booker, and Bates only managed to play three games and take the field for 105 snaps.

Poles traded a 2025 seventh-round draft pick to the Cincinnati Bengals for running back Khalil Herbert. Herbert was a fan favorite, but he had fallen to RB4 on the depth chart and just wasn’t seeing the field.

Poles also traded for a 2022 second-round draft pick and a 2023 sixth-round draft pick from the Los Angeles Chargers in exchange for linebacker Khalil Mack. Mack has averaged over 10 sacks per season and made the Pro Bowl in all three seasons with the Chargers. Perhaps the Bears would have had to eat a little of Mack’s contract to get a larger return.

Poles traded for a 2023 fourth-round draft pick from the Philadelphia Eagles in exchange for defensive end Robert Quinn. Quinn played in six games for the Eagles and had two tackles and zero sacks. A fourth-round pick for that production is highway robbery.

Poles traded a 2025 sixth-round pick to the Seattle Seahawks for defensive lineman Darrell Taylor. Taylor had a huge game in his debut with the Bears, but that accounted for 67% of his sacks and 25% of his tackles for the season.

Poles traded for offensive lineman Jonah Jackson from the Los Angeles Rams in exchange for a 2025 sixth-round pick. Jackson hasn't played a snap for the Bears at this point, but the trade is already a top-four trade in Poles’ history.

Poles traded for defensive lineman Montez Sweat from the Washington Commanders in exchange for a 2024 second-round pick. This trade looked fantastic in 2023 but didn’t age as well in 2024 as Sweat’s impact was significantly down this past season.

Poles traded for wide receiver Keenan Allen from the Los Angeles Chargers in exchange for a 2024 fourth-round pick. Allen looks like he will just spend one season in Chicago, and despite a mess of an offense, Allen was a key contributor.

Poles traded for offensive lineman Joe Thuney from the Kansas City Chiefs in exchange for a 2026 fourth-round pick. The Chiefs have been in a tight spot after they decided to give Trey Smith the franchise tag which would have forced them to pay a fourth offensive lineman north of $18 million a year.

Poles traded for wide receiver DJ Moore, the No. 9 pick in the 2023 draft, a 2024 first-round pick, and a 2025 second-round pick from the Carolina Panthers in exchange for the No. 1 pick in the 2023 draft.

The Bears' Big Moves: Ryan Poles' Trading Game

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