Ranking Every Trade Of The Ryan Poles Era As Bears General Manager

On January 25th, 2022, Ryan Poles took over as the general manager of the Chicago Bears. Nobody knew what to expect. The best knowledge available at the time was that he’d been a quality executive for the Kansas City Chiefs, helping them win the Super Bowl in 2019. He had also briefly been a member of the Bears’ roster in 2008 as an undrafted free agent. By all accounts, he impressed in the interview process so much that team chairman George McCaskey decided to pick Poles up at the airport personally to make the hire official.

That didn’t matter much to Bears fans. Their only concern was how Poles would handle the big chair. How would he draft? How would he sign free agents? Perhaps most interestingly, how would he approach the trade market? Well, we’ve received answers to all of those questions. As of writing this, Poles has engineered 32 trades over his five offseasons in charge. That led to an interesting debate. Which of them was the best?

To that end, I decided to dig through the entire inventory and rank every single trade Poles has made. In the interest of fairness, every 2026 transaction will be excluded because it’s impossible to determine their quality. These will strictly be the 28 moves between 2022 and 2025. Can you guess the top five?

Ryan Poles has a wider range of trade quality than any GM

28. Chase Claypool trade (2022)

• Bears received: WR Chase Claypool
• Steelers received: 2023 2nd-round pick (No. 32 overall, used on CB Joey Porter Jr.)

Probably not a surprise to anybody. The initial intent of this trade made sense. Chicago badly needed another weapon for Justin Fields. It’s just that Claypool had not been a good enough player by that point to warrant surrendering a 2nd round pick. There were already red flags. Questions about the receiver’s commitment to the game. His seeming love of the attention. The fact that Mike Tomlin, one of the best coaches in the league, was souring on him. Poles ignored all of that and still sent what was technically a 1st round pick (32nd overall) to Pittsburgh for the receiver. Not only did Claypool crash and burn in Chicago (191 yards and a TD in 10 games), but the Steelers landed a quality starting corner in the process. A position the Bears had serious needs.

27. Ruben Hyppolite trade (2025)

• Bears receive: 132nd overall pick (LB Ruben Hyppolite) and 169th overall pick (CB Zah Frazier)
• Bills receive: 109th overall pick (used on DL Deone Walker)

This is a classic case of how trading down isn’t always the grandiose solution people think it is. Poles wanted an extra pick to give the Bears some flexibility. What he got was not one but two disappointing players. Hyppolite was injured in his first year with the team. Frazier never even practiced with the team before getting cut. Meanwhile, Walker became a solid rookie contributor on a Buffalo defense that finished 7th in the NFL last season. A bad case for quantity over quality.

26. N’Keal Harry trade (2022)

• Bears received: WR N’Keal Harry
• Patriots received: 2024 7th-round pick (used on TE Jaheim Bell)

Taking fliers on former 1st round picks isn’t a terrible idea. You never know. One of them may end up igniting their career if given a fresh start. Ryan Poles likely hoped that might be the case for Harry, who’d floundered during his time in New England. It didn’t pan out. The receiver played just seven games for Chicago, catching seven passes for 119 yards and a touchdown. He was allowed to leave the following offseason and was out of football by the end of 2024.

25. Ryan Bates trade (2024)

• Bears received: OL Ryan Bates
• Bills received: 2024 5th-round pick (used on OL Sedrick Van Pran-Granger)

Ryan Poles had been chasing this white whale for a long time. He tried to sign Bates as an unrestricted free agent in 2022, but Buffalo matched the offer. Two years later, the Bears GM got his guy. The result? Underwhelming. Bates’ first season with the team was marred by injuries and he only played three games. By the time he was finally back healthy last season, the Bears had completely revamped their interior offensive line. This relegated him to backup, and he was quietly allowed to walk this off-season.

24. Joe Tryon-Shoyinka trade (2025)

• Bears received: DE Joe Tryon-Shoyinka
• Buccaneers received: 2026 7th-round pick swap

The former 1st round pick arrived with lots of promise in Tampa Bay. Unfortunately, he never quite found his footing there, or in Cleveland. The Bears, desperate for death as injury hit their defensive line last season, decided to take a flier on him. Did it amount to anything? Not really. Tryon-Shoyinka managed five quarterback pressures in eight games for the team. He didn’t play in either playoff game.

23. Dan Feeney trade (2023)

• Bears received: OL Dan Feeney.
• Dolphins received: 2024 6th-round pick (used on S Patrick McMorris)

The offensive line was a mess in 2022. It is hardly surprising the Bears would hunt for any help they could find. Feeney had starting experience from his time with the Chargers and Jets. It was a worthwhile idea to maybe get some stable protection for Fields. In the end, Feeney didn’t do much. He started one game and served the rest of the season as a backup.

22. Doug Kramer trade (2022)

• Bears received: Pick No. 166 (subsequently traded) and No. 207 (used on C Doug Kramer).
• Texans received: Pick No. 150 (used on DL Thomas Booker)

The trade itself was unremarkable. A late-round move that gave the Bears an extra pick. Houston didn’t get anything out of Booker, and he’s now out of the league. Kramer was more of a feel-good story. A Hinsdale, Illinois native plays for his home-state college program and does well enough to get drafted by his home-state NFL team. He even made some minor contributions on the field.

21. Robert Quinn trade (2022)

• Bears received: 2023 4th-round pick (used on WR Tyler Scott)
• Eagles received: DE Robert Quinn

Quinn fired his last great shot as a pass rusher in 2021, collecting 18.5 sacks. Through the first half of 2022, he’d lost steam. It was apparent his clock was ticking. So for Poles to somehow finagle a 4th round pick for him, from Howie Roseman no less, was a major victory. It almost could’ve been a home run, too. Nick Herbig, Pittsburgh’s productive pass rusher, went one spot before Tyler Scott in the 4th round of that subsequent draft. Instead, the Bears were another of the many teams that probably should’ve taken Puka Nacua.

20. Chris Williams trade (2024)

• Bears receive: DT Chris Williams and a 2025 7th round pick (subsequently traded)
• Browns receive: 2025 6th round pick (traded for OG Bryce Cabeldue)

Defensive line depth was a serious issue for the Bears going into 2024. Poles chose to approach it in a way that has become unique to him. He sought out cheap trade options. Williams was one of them. The defensive tackle showed flashes in a crowded depth chart for Cleveland. Perhaps some added opportunities might allow him to blossom. In truth, he kind of did. Williams had a career-high three sacks and seven quarterback hits with the Bears that season. He added another sack in 2025. It wasn’t a home run, but for what the Bears paid, it was a solid move.

19. Dominique Robinson trade (2022)

• Bears received: Pick No. 174 (DE Dominique Robinson) and No. 226 (G Ja’Tyre Carter)
• Bengals received: Pick No. 166 (used on DL Tycen Anderson)

Trading back and still finding value is something that is deceptively difficult for NFL general managers. Given Ryan Poles credit. He’s been pretty good at it during his tenure. Looking at this trade in a vacuum, the Bears got the best player of the bunch. Robinson wasn’t anything special. He didn’t blossom into the talented pass rusher they hoped. Still, he eventually became a decent rotational guy who was a solid run defender.

18. Elijah Hicks trade (2022)

• Bears received: Two 2022 7th-round picks: No. 254 (S Elijah Hicks) and No. 255 (P Trenton Gill).
• Chargers received: 2023 6th-round pick (used on OT Scott Matlock)

Something else Poles does that some general managers are too nervous to do is trade back into a draft after running out of picks. That involves giving up a future pick for the privilege. Once again, the Bears GM did pretty well. Gill was an average punter at best during his stint with the team, but Hicks has become one of their core special teams players and a solid backup safety.

17. Darrell Taylor trade (2024)

• Bears received: DE Darrell Taylor.
• Seahawks received: 2025 6th-round pick (used on WR J.C. Latham)

One part of two trades the Bears made late in the offseason to boost their pass rush. This was the bigger of the two. Taylor had been a decent player in Seattle, but was caught in a numbers game. Chicago had a vacancy available. While he didn’t recapture the early magic from his Seahawks run, Taylor did give the Bears three sacks and nine QB hits in his single season of work.

16. Roschon Johnson trade (2023)

• Bears received: Pick No. 115 (RB Roschon Johnson) and No. 165 (CB Terell Smith).
• Saints received: Pick No. 103 (used on OL Nick Saldiveri)

Again. Poles makes a trade back in the draft and comes out on the better end of the deal. This time, he lands a decent backup running back in Johnson, who has also had some good moments on special teams. Smith became a rock solid CB4 on defense, able to step in for Jaylon Johnson or Tyrique Stevenson whenever needed. Getting two such players by moving down 12 spots in the 4th round is pretty good work.

15. Tyrique Stevenson trade (2023)

• Bears received: Pick No. 56 (CB Tyrique Stevenson)
• Jaguars received: Pick No. 61 (used on TE Brenton Strange) and No. 136 (used on OL Yasir Abdullah)

Ryan Poles doesn’t trade up in the draft. At least he does it very rarely. One of the few instances in his career happened in 2023 when he moved up for Stevenson. Make no mistake. The career of the young cornerback has been volatile, to say the least. He’s had moments of brilliance intermixed with moments of mind-numbing stupidity. From the Hail Mary fiasco to his season-saving forced fumble against Dallas, his career in Chicago certainly hasn’t been boring.

14. Darnell Wright trade (2023)

• Bears received: Pick No. 10 (OT Darnell Wright) and a 2024 4th-round pick (P Tory Taylor).
• Eagles received: Pick No. 9 (used on DT Jalen Carter)

This might be called Poles’ greatest heat check. He’d already completed a monumental trade you’ll see later in the countdown. Everybody thought he’d rest on his laurels and take his preferred player. Instead, he swings another minor trade down from #9 to #10, passing on blue-chip prospect Carter in the process. It was the mother of all “feeling it” moments. The best part is that he still ended up landing an All-Pro player. Chicago secured Wright, who is now one of the top right tackles in all of football.

13. Justin Fields trade (2024)

• Bears received: 2025 6th-round pick (traded for Jonah Jackson)
• Steelers received: QB Justin Fields

It was a somber moment. Fans loved Fields for his competitiveness and highlight-reel plays as an athlete. They wanted him to succeed so badly. Sadly, it became apparent he just lacked certain vital traits one needed to be a franchise quarterback. Wanting a fresh start at the position, Poles gave Fields an opportunity to reignite his career with a stable organization in Pittsburgh. The pick they got in return was eventually flipped for a player who helped the Bears return to the playoffs after seven seasons.

12. Chase Claypool trade (2023)

• Bears received: 2025 6th-round pick (which was later used to get Chris Williams)
• Dolphins received: WR Chase Claypool and a 2025 7th-round pick

Rest assured, the fact that Poles got anything in return for Claypool must be considered a minor miracle. That was how bad the mercurial receiver had been in Chicago, both on and off the field. The Bears got a pick back that was later used to acquire a decent defensive line option. Williams contributed far more to the team than Claypool ever did. Though a backup last season, he still made some important plays to get them to the postseason. Getting that for a player the Bears probably would’ve ended up cutting is a big win.

11. Austin Booker trade (2024)

• Bears received: 2024 pick No. 144 (DE Austin Booker)
• Bills received: 2025 4th-round pick (TE Mitchell Evans)

Another of those trading back into a draft to get a player he wants by Poles here. Once again, he actually pulls it off pretty well. While Buffalo failed to capitalize on the future pick, the Bears got themselves probably the most promising young pass rusher on their entire roster. After a false start to his second season, Booker finished 2025 on a bit of a hot streak with 4.5 sacks in his final six games. He looks like he’s poised for a breakout year this season, which would make this trade look even better.

10. Ozzy Trapilo trade (2025)

Bears received: Pick No. 56 (OT Ozzy Trapilo), Pick No. 62 (DT Shemar Turner), and Pick No. 109 (later traded)

Bills received: Pick No. 41 (used on DT T.J. Sanders), Pick No. 72 (used on DE Landon Jackson, and Pick No. 240 (used on WR Kaden Prather)

This is probably the most volatile trade on the entire list. It could easily drop to the bottom or rise to the top five. Everything depends on what happens with Ozzy Trapilo. The big left tackle was playing really good football towards the end of last season. He looked like a possible franchise guy at a critical position. Then he tore his patella against Green Bay in the playoffs. Now his future is on hold as he recovers from that. Nobody can say for sure what he’ll be when he eventually returns. If he picks up where he left off, this trade will be a major win for the Bears. If not, it’s an outright dud.

09. Keenan Allen trade (2024)

• Bears received: WR Keenan Allen.
• Chargers received: 2024 4th-round pick (used on LB Junior Colson)

Getting Caleb Williams another legitimate weapon was a top priority for the Bears in 2024. Poles has always been good at finding unexpected bargains from time to time. Allen was a perfect example. The former Pro Bowl receiver faced a crossroads in Los Angeles. The team didn’t want to pay his hefty contract. Chicago brought him aboard and he instantly became a nice security blanket for the rookie quarterback. Though he only had 744 yards, Allen did score seven touchdowns.

08. Khalil Mack trade (2022)

• Bears received: 2022 2nd-round pick (S Jaquan Brisker) and a 2023 6th-round pick (DL Travis Bell)
• Chargers received: LB Khalil Mack

Poles understood reality from the start. The Bears were approaching salary cap hell and had no assets to help rebuild what had become an old and depleted roster. So, he decided to rip the Band-Aid off. Mack was their biggest defensive name and still had plenty of value. Getting a 2nd round pick for him felt underwhelming, but it was close to what was expected. Chicago turned that into Brisker, who was an above-average starting safety for the team across four seasons. It wasn’t enough to earn a second contract, but Brisker was a key contributor on that 2025 playoff team.

07. Roquan Smith trade (2022)

• Bears received: LB A.J. Klein, a 2023 2nd-round pick (DT Gervon Dexter), and a 2023 5th-round pick (LB Noah Sewell)
• Ravens received: LB Roquan Smith

This is one of those trades that creates mixed feelings. Fans loved Smith. He was a great player and a key part of the defense since he was drafted. Unfortunately, business got in the way. The Bears were entering a rebuilding phase, and Smith wanted a new contract. Poles made the tough decision to flip him to Baltimore for picks and cap space. The linebacker has remained an excellent player out east, to nobody’s surprise. Still, Chicago did make good on the return. Gervon Dexter has been a good defensive tackle for them across three seasons, collecting 13.5 sacks. Sewell has started some games for them as well.

06. Braxton Jones trade (2022)

• Bears received: Pick No. 168 (LT Braxton Jones) and No. 203 (RB Trestan Ebner)
• Bills received: Pick No. 148 (WR Khalil Shakir)

In almost every scenario involving the draft, the only way to acquire a legitimate left tackle is either by holding a high draft pick to begin with or trading for one. So, for Ryan Poles to land one after trading down in the 5th round? That is pretty impressive. Jones might not be the most popular player among fans these days, but you can’t deny he’s at least been serviceable for most of his tenure with the Bears. Certainly better than a healthy number of other left tackles in the league. Injuries have hampered his progress over the past year. It will be interesting to see how he handles this opportunity to compete for the job again in 2026.

05. Khalil Herbert trade (2024)

• Bears received: 2025 7th-round pick (used on RB Kyle Monangai)
• Bengals received: RB Khalil Herbert

Herbert had been a solid rotational running back for the Bears, but it was evident that the new offensive coaching staff, led by Shane Waldron, didn’t see him as a good fit. Poles was eventually able to flip him to Cincinnati for a late pick at the trade deadline. Most people didn’t think much about it. They couldn’t have known the pick would become a central contributor in a top 10 offense. Monangai collected 947 yards from scrimmage as a rookie, scoring five touchdowns along the way. His pairing with D’Andre Swift became the perfect yin and yang for Chicago’s division-winning rushing attack last season.

04. Jonah Jackson trade (2025)

• Bears received: OL Jonah Jackson
• Rams received: 2025 6th-round pick (later traded)

People don’t understand how things went so wrong for Jackson in L.A. He’d been a Pro Bowl player in Detroit before leaving in 2024 for the west coast. Then injuries struck, and he was eventually benched. Some thought his career as a high-level guard was behind him. The Bears were willing to roll the dice. Poles gave up a late-round pick and even handed Jackson a minor contract extension. The team was rewarded with a major bounce-back year from the guard. He was a core part of an offensive line that allowed just 24 sacks and blocked the 3rd-ranked running game. Jackson had a case for making his second Pro Bowl.

03. Montez Sweat trade (2023)

• Bears received: DE Montez Sweat.
• Commanders received: 2024 2nd-round pick (used on TE Ben Sinnott)

This move was heavily criticized at the time. Many felt Ryan Poles flipping a 2nd rounder for a veteran player so early in a rebuild was reckless. That was especially true, knowing they’d have to hand Sweat a lofty contract as well. All things considered, that move looks better every day. Sweat has 22.5 sacks, 48 QB hits, 27 tackles for a loss, and six forced fumbles in 44 games with the Bears. People complain about the pass rush not being good enough. Try to imagine what it would look like right now if Poles hadn’t secured Sweat.

02. Joe Thuney trade (2025)

• Bears received: OL Joe Thuney
• Chiefs received: 2026 4th-round pick (DE Abdul Carter)

It’s rare for a team to commit highway robbery by flipping a mid-round pick for an aging player. Somehow, the Bears did that when they plucked Thuney from Kansas City. Poles had deep connections to the Chiefs. He knew the type of player Thuney was and the immense boost he’d give the new offense under Ben Johnson. This was a future Hall of Fame guard. If they got him at 70% of the player he was at his peak? It’s a win. What they got was a first-team All-Pro who was voted Offensive Lineman of the Year. An absolute home run.

01. The #1 Pick Blockbuster (2023)

• Bears received: WR D.J. Moore, Pick No. 9 (subsequently part of OT Darnell Wright trade), Pick No. 61 (subsequently part of CB Tyrique Stevenson trade), 2024 1st round pick (used on QB Caleb Williams), and 2025 2nd round pick (used on WR Luther Burden)
• Panthers received: Pick No. 1 (used on QB Bryce Young)

There are few trades in Bears history that can be called truly seismic. Something that changed the direction of the entire franchise in one instant. That was this blockbuster deal with the Carolina Panthers in March of 2023. Ryan Poles knew the state of his team. It was in a rebuilding phase with holes across the roster. Everybody expected him to take a quarterback with the #1 overall pick. The problem was that he still had a QB people wanted to keep exploring (Fields). Besides, even if he’d taken a quarterback, that player would’ve been surrounded by a poor supporting cast.

So, the Bears flipped the pick to Carolina. What they got in return was a good wide receiver who had one of the best seasons in franchise history (1,364 yards that first season) and made two of the most important catches in franchise history (OT against Green Bay and the playoff winner against Green Bay). Would you believe that wasn’t the best part? They also landed the pick that became Caleb Williams, their first franchise quarterback in decades. Last but not least, they added Burden, one of the most dynamic playmakers they’ve had at receiver in a long time.

Many see the Bears as Super Bowl contenders, and it all originates from that trade three years ago.