Nobody expected the Chicago Bears to win the NFC North title last season. So when they did, it was an understandable shock. The Bears had been the worst team in the division for the past four seasons. They had a new coaching staff and an unproven quarterback. It would take time to get things going. Their 0-2 start seemed to prove that. Then they won 11 of their last 15, swiping the crown, and beating Green Bay in the wild card playoff. One would think this success would bring the Bears some credibility.

Not so much. It appears NFL experts aren’t buying the idea that this team is the true king of the North. ESPN analytics proved it when it revealed the latest odds on who will win the division in 2026. Not only were the Bears not the favorites, but they also weren’t even the second-favorite.

It’s pretty apparent that much of the pessimism stems from not being established. Detroit won back-to-back division titles in 2023 and 2024 before a disappointing 9-8 season last year. Green Bay has been a regular playoff participant for years. They’re safer bets.

The Chicago Bears are victims of not getting better on paper.

Many feel they lost a healthy chunk of what made them successful last season. Kevin Byard and Nahshon Wright, who combined for 12 interceptions, left for the Patriots and Jets, respectively. Tremaine Edmunds, their most productive linebacker, was released. Beloved Packer killer D.J. Moore was traded to Buffalo. Pro Bowl center Drew Dalman retired. All of this happened while the team also didn’t appear to fix their lingering pass rush issues. You can at least understand that line of thinking.

Yes, they still have quarterback Caleb Williams and head coach Ben Johnson, but it feels like the roster is in a transitional phase. In reality, the Bears are banking on some of their young talent taking on bigger roles this season. That goes especially for tight end Colston Loveland and wide receiver Luther Burden. Both were terrific as rookies last season and seem poised for breakouts. Kyle Monangai played great as well. He isn’t going anywhere. The Bears also added Coby Bryant, Devin Bush, and Dillon Thieneman on defense.

So it’s not like the cupboard suddenly went bare.

Coach Johnson was right.

He said after the season that the Chicago Bears were starting back at the bottom of the mountain. Everything starts over from zero. They must climb up again. He meant this in reference to the idea that the team could carry the momentum of their 2025 success into this year. Johnson dismissed that idea. He knows that the modern NFL doesn’t work that way. Rosters change so frequently that it is impossible to sustain momentum in the conventional sense. After watching the team unload so many key players, it’s clear he knew what he was talking about.

Still, the core names remain in place. Williams should take another step forward at quarterback. Johnson’s offensive play-calling won’t suddenly stop being really good. People can debate their tough strength of schedule, but the reality is that no schedule is predictable. Unexpected things always happen. It’s the teams who adapt quickly that thrive, and the Bears proved last season they could do that.

Training camp is about to begin. Less than a week separates the Chicago Bears from beginning preparations for the 2026 season. Head coach Ben Johnson is determined to improve on the team’s accomplishments last year. That likely means a tough, competitive grind that will push his players to the limits of their mental and physical endurance. All the while, general manager Ryan Poles is left with a dilemma. Has he made every move possible to get this team ready? If we’re being honest, no. The Bears really should consider making one more run at Taylor Decker.

The former Pro Bowl left tackle remains unsigned. It’s been months since the Detroit Lions unceremoniously cut him after a decade of service. Like most unfortunate outcomes, this happened over a money disagreement. Now Decker faces a career crossroads. Last season proved he can still play at a high level. There is certain to be interest from around the league. Chicago has a glaring hole at left tackle. Kristopher Knox of Bleacher Report believes they should make another run at him.

Would Taylor Decker listen?

The fact that veteran left tackle Taylor Decker even became available this offseason was surprising. The longtime Detroit Lions starter was under contract for the 2026 season but was granted his release after he and the team failed to work out a revised contract.

And by “revised contract,” we mean that the Lions asked Decker to take a pay cut.

Decker is available now, and while he’ll turn 33 next month, he’s still capable of filling a starting role. According to Pro Football Focus, Decker allowed just two sacks in 2025 while grading out as the 41st overall offensive tackle.

At this point in his career, Decker would make the most sense for a legitimate contender looking to add some insurance to its offensive line. The Chicago Bears and Los Angeles Rams spring to mind.

Decker is confronted with a harsh reality.

He’d always hoped to play his entire career in Detroit. That was the plan. The man clearly wasn’t ready for the possibility that the Lions would be willing to move on. Everybody felt Chicago was an obvious landing spot. They needed a proven left tackle to fortify their offensive line. Johnson had been his coach for three years when he was Detroit’s offensive coordinator. It was a natural fit. Yet rumors indicated the left tackle couldn’t bring himself to consider joining the Bears. To him, it would be a betrayal of all that time and effort he put into the Lions’ success.

There were too many conflicting emotions about signing with a division rival. One would’ve thought Taylor Decker would just sign elsewhere. That hasn’t happened. Some wonder if he may just retire. He’s in his mid-30s. The wear and tear on the body really starts to show around that age for offensive linemen. The only true reason for him to keep playing is the pursuit of that elusive Super Bowl ring. For some, that isn’t enough. Decker might be content to call it a career.

The Bears should make one more pitch.

As of right now, their left tackle situation remains unsettled. Most agree that veteran Braxton Jones is the favorite to claim the starting job. His leg is finally healthy after it hampered his performance last season. He is the most experienced of the options and knows the offense. Former 1st round pick Jedrick Wills has the talent advantage, but he hasn’t played in over a year. Theo Benedet has added some good weight since last year, but his limitations haven’t changed. Kiran Amegadjie is still in the mix as well. Yet nothing suggests he is a serious contender at this stage.

Are any of those options better than Decker? No, they are not. If the Bears see the Super Bowl as their endgame this season, then leaving the left tackle position in the hands of somebody like Jones or Wills feels too risky. They need a proven commodity. Decker knows this offense. He played the best football of his career in it. While he may no longer be in his prime, it isn’t crazy to believe he has one more good season left in him. The Bears have six days left to make one more pitch. They should take it.

NFL merchandise is fairly predictable these days. You have the classic team-oriented shirts, hats, and other assorted wear. They do get creative sometimes, often when certain players establish themselves as fan favorites or pull off highly memorable plays. We recently saw that with the Chicago Bears Caleb Williams “Jumpman” play against the Green Bay Packers. People quickly put that silhouette on a shirt. However, every once in a while, the league does something that is actually pretty interesting.

Crossovers.

This is where they merge team paraphernalia with pop culture. According to Adam Schefter, the big reveal this year is a limited-edition Disney clothing line. Every NFL team will have shirts and jerseys featuring actual Disney characters. Each will fit with the theme of each team. The Las Vegas Raiders have Darth Vader. The Tampa Bay Buccaneers have, of course, Captain Hook. All Disney properties are in play, meaning there is no shortage of options for every team. The full reveal is supposedly coming next month.

Who will be the Chicago Bears’ mascot?

Naturally, it will be a bear character. That part is the no-brainer. The trickier question is which bear? You’d be surprised how many notable bears have come under the Disney umbrella in the past century. Probably the first famous one was Humphrey Bear, a bumbling character from the 1950s cartoons. Modern fans may think of Kenai and Koda from the movie Brother Bear. You also can’t forget Disney owns the Muppets, which means the legendary Fozzie Bear is also a possibility.

That said, if brand recognition is the primary goal with this crossover, then there are only two realistic candidates. One is Baloo, the grey bear of Jungle Book and Tailspin fame, best known for his timeless classic song, “The Bear Necessities.” The other is the iconic Winnie the Pooh, the forever beloved golden bear, known for his soft heart and endless love of honey.

Either would be a fantastic choice. Baloo probably fits the Chicago Bears’ aesthetic better. However, you can probably say that Winnie would sell more merchandise because of his rampant popularity.

Say this for the NFL. Their marketing ability is as savvy as ever.

The league was smart enough to lean into the growing relationship between star tight end Travis Kelce and pop superstar Taylor Swift when it happened. That brought millions of new eyes to the product. Now they’re looking to do the same with the legions of Disney fans. Tons of cash is coming their way. It is another reminder that the NFL media machine is light-years ahead of every other sports league in the United States. No doubt the Chicago Bears hope their character choice delivers as hoped.

Keep an ear out for the announcement in August. The Hall of Fame game takes place on the 6th. It wouldn’t be surprising if the league plans it around that time when the most eyeballs will be watching. Every fan is desperate for football to return. It will be a perfect advertising opportunity. Get those wallets ready, Bears fans. This should be a fun addition to your collections.

Caleb Williams knew that winning over Chicago Bears fans would be difficult. Sure, he was the #1 pick in the draft. That came with a certain degree of hope. Still, this was a fanbase that had been burned by countless 1st-round quarterbacks in the past. Mitch Trubisky failed. Justin Fields failed. Why should they think he’d be any different? To show them that he was serious about changing the organization’s culture, Williams needed a way to connect with them and understand them. It didn’t take long to find it.

Hatred of the Green Bay Packers.

The quarterback quickly realized that if he took up the call of war against the Bears’ eternal rivals, he might get everybody believing in the franchise’s direction. It couldn’t just be about winning games, though. Williams had to take it a step further. He must go out of his way to take digs at the Packers at every opportunity. He certainly did that. He’d encourage ‘Green Bay Sucks!’ chants at restaurants. He’d retweet insults on Twitter. Everything came to a head following the 2025 wild card win in the playoffs, when he literally shaved a block of cheese on the national broadcast.

Caleb Williams isn’t above targeting specific players, it seems.

Up until now, the Bears quarterback has kept his jabs general. It’s all about needling the Packers organization itself. However, it seems he doesn’t mind narrowing his focus to specific players. It is common knowledge that Green Bay fans insist up and down that their quarterback, Jordan Love, is the superior player to Williams. Ball-knowers see it. Blind Bears fans can’t. Unfortunately, there are things called stats that help paint a clearer picture, and Love doesn’t come off well. Williams made sure to highlight one sensitive spot for Green Bay’s signal caller.

For years, Bears fans have argued with Packers fans that it’s Love who is overrated. Sure, his numbers look good on paper. Yet the moment you start digging deeper, they get worse and worse. His accuracy on deep throws is only one example. Not enough people talk about how he performs when under pressure. Through three seasons, Love has 12 touchdowns, 12 interceptions, and a completion percentage below 48%.

Then you have the clutch factor.

This last one is a hotly contested topic. Love has won some big games in his career. There is no doubting that. The problem is that evidence is mounting that he just can’t seem to handle crunch time as either of his predecessors could. Think about this. Love has now played in four playoff games with Green Bay. He has nine touchdowns and five interceptions across that time. The crazy part is? Four of those touchdowns came in a four-quarter span, with the first half against Dallas in 2023 and the first half against Chicago this past January. In the other 12 quarters? He has five touchdowns and five interceptions. While only being sacked three times, mind you.

Not to be outdone, his performance in the 4th quarter is also underwhelming. He’s completing barely 58% of his passes with 22 touchdowns and 12 interceptions. This showed up in a big way against Caleb Williams. After throwing three touchdowns in the first half against Chicago, Love only managed six points in the second, with his lone TD being a bubble screen that Matthew Golden took for the score. Then, on the biggest drive of his career, Love went 5-of-11 with his last three passes all being incompletions.

Drafting Colston Loveland was a surprise last year. Fans didn’t see it coming. While they knew tight end was a possibility, they expected Penn State’s Tyler Warren as the likely target. What many don’t know is it was also a surprise to Loveland himself. He hadn’t conducted a private meeting with the Chicago Bears in advance of the draft. The only time they met was at his Michigan pro day. Loveland took that to mean they were probably leaning in a different direction. So the announcement on opening night came as a shock.

Part of it was also because the tight end felt he had a strong idea of where he would end up. During an appearance on Bussin’ With The Boys, he revealed that every indication going into draft night was that the Los Angeles Chargers were his likely landing spot.

Los Angeles was recently taken over by new head coach Jim Harbaugh, who, of course, recruited and developed Loveland at Michigan. If anybody understood what the tight end was capable of, it’d be him. There was one problem. The Chargers didn’t pick until 22nd overall. That gave other teams a chance to steal him. A chance the Bears seized.

“I was definitely surprised. Like, I was, in my head, I’m thinking no later than the Chargers, but I’ll probably go like that. That was kind of what I was thinking. So when they (the Bears) picked me up, I was definitely surprised, but I kind of knew (at my) pro day we met, and I feel like I killed that shit, you know? Yeah, I think I did good.”

The Bears were very fortunate to get Colston Loveland.

Not enough people talk about how Harbaugh’s decision to take the Chargers job was so important. Imagine if he’d gone to the Las Vegas Raiders instead. He had ties to the organization from his time as an assistant coach and had flirted with the idea in years past. That team held the 6th pick in the 2025 draft. Even if Harbaugh had improved their record, they likely would’ve been in a much better position to go after Loveland in the 1st round. The Chargers were way too far out of range to even consider trading up.

Thinking back on it now, that isn’t a world the Bears want to live in. Colston Loveland is the first true non-QB with star potential they’ve drafted in years. We’re talking Brian Urlacher-level capability. His rookie season was outstanding, as he led the team with 713 yards and 6 touchdowns. Everybody knows what having a star tight end can do to the fortunes of a franchise. Look at Travis Kelce, George Kittle, and Rob Gronkowski. Opponents have few answers for them, especially when in the hands of elite play callers like Ben Johnson.

The truth is, Harbaugh had no shot at Loveland.

Even if the Bears had passed on him for some reason, it was well-documented that several teams were trying to trade up to get him. The likely scenario was that a team would jump somewhere between picks 11-13 to get him, making sure to get in front of the Colts at #14. Remember, they ended up selecting Warren. Maybe the Chargers were one of those teams, but the way they’ve operated over the past three years doesn’t back up that possibility. They haven’t been known for aggressive moves in the 1st round.

Ultimately, Chicago took advantage of their high draft position. Johnson recognized immediately what Colston Loveland could do. No doubt his background as a tight ends coach helped with that. Get him in the right situations, and he’d be impossible to cover. There were already signs of it last season. The training wheels are off now.

The Chicago Bears lost some notable free agents this offseason. Kevin Byard left for New England. Nahshon Wright departed for New York. C.J. Gardner-Johnson went to Buffalo. It was a tough blow to the secondary. However, the one that seemed to hit the hardest was Jaquan Brisker. Those other names, while very good players, were free agent additions. They’d arrived as mercenaries meant to help the team in the past couple of seasons. Brisker was different. He was a homegrown talent the Bears drafted in the 2nd round in 2022.

They’d viewed him as part of their rebuild. By and large, that mission was accomplished. Brisker was a central part of their defense during the long process, culminating in that division title last season. It’s rather fitting that one of his best games was his last in the loss to the Rams. Sadly, the business of the NFL caught up. Facing a serious cap crunch, the Bears had some tough decisions. That meant having to let several players leave in free agency. Brisker was one of them. His exit was surprisingly quiet, given his outspoken presence online. Well, that silence was finally broken as the safety delivered a heartfelt message to Bears fans.

Jaquan Brisker let the emotions flow.

“Very Very Overdue.. The fans and city of Chicago deserve this! To the city of Chicago, it’s been nothing but Love since the day I was drafted! The love, energy, passion of the fans I felt it immediately. Thank you for letting me live my DREAM, hearing my name called and being drafted! Also, welcoming my family and I for 4 wonderful years. Everything we been through from the start to get to here , it’s been a JOURNEY! One where these memories will last forever. Can’t say enough but great things about the city of Chicago and their beautiful fans! I Appreciate the fans for always showing up, no matter what you guys stay true! I mean it from the bottom of my heart, I will forever love you, all the memories, everything.

Seeing the 9 jerseys all around the stadium with the Brisker on the back was special and will always go a long way! I left it better than what I found it ! To my teammates, I thank you .. The love, support, memories, and brotherhood we built together over the years will forever go far! My Brothers for life. Grateful for the organization and every fan who loved me through it all. Y’all changed my life. Forever a bear. This will always be my home.”

Brisker built a strong legacy in Chicago.

There were no controversies with the safety during his time here. He showed up, worked hard, played hard, and did everything he could to galvanize the team to success. It was reflected in his play. Brisker always played with a downhill, aggressive style. He collected 342 tackles in four seasons, seven sacks, four interceptions, and four forced fumbles. Just solid all-around production. Under normal circumstances, the Bears probably would’ve chosen to retain him. Cap issues made it impossible.

There was also the Dennis Allen factor. Chicago’s defensive coordinator wasn’t the one who drafted Brisker. He was a product of the previous coaching staff. It would make sense that he would prefer to bring in safeties that fit his vision. It happens all the time. Brisker has no reason to feel bitter. He got to return to his home state of Pennsylvania and sign with the Pittsburgh Steelers. If he maintains his solid play, Brisker should have no problem building a future there.

Was Brisker a hit or a miss?

This will be a topic some Bears fans debate. Usually, with 2nd round picks, you hope they become long-term starters for your franchise. In reality, only 35-40% of safeties selected in that range actually receive a second contract from the teams that drafted them. That isn’t to say Jaquan Brisker didn’t deserve one. It came down to priorities. The Bears felt they would have an easier time replacing losses at safety than they would’ve at more premium positions like defensive line and cornerback.

Don’t forget they signed Byard to a modest deal two years ago. They picked Gardner-Johnson off the street. You can find good safeties with a bargain approach. That said, based on how their offseason went, it is hard to argue that the Bears didn’t upgrade, at least from a talent perspective. They signed Super Bowl champion Coby Bryant in free agency and spent their 1st round pick on Dillon Thieneman. None of this means Brisker won’t be missed. As 2nd round picks go, he’s been one of the better ones they’ve had in a long time.

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.