The Seattle Seahawks have fired the first shot ahead of the 2026 trade deadline. They flipped two draft picks to the Indianapolis Colts for 8-time Pro Bowl guard Quentin Nelson. It seems pretty clear the team is eager to chase a second straight Super Bowl title and is willing to gamble on a half-year rental (Nelson is a free agent in 2027) to get it done. This has naturally kicked off a firestorm on social media, with fans calling on their teams to start making movies. The Chicago Bears are atop that list. That falls at the feet of general manager Ryan Poles.

While the man has never been afraid to make aggressive moves at the trade deadline before, he’s been rather quiet for the past two years. The Bears opted for bargain purchases in 2024 and 2025, adding depth pieces that didn’t really shift the bottom line. Now with the team 5-2 and well-positioned for a deep playoff run, it feels like the time is perfect for a genuine big swing. However, it is possible Poles may not feel the same way. He may not think the risk is worth it, especially after watching events elsewhere.

Ryan Poles may not want to become like the Rams.

Don’t forget, Los Angeles went all in this offseason with two blockbuster trades. First was for Pro Bowl cornerback Trent McDuffie from Kansas City. Then they nabbed superstar pass rusher Myles Garrett from Cleveland. Those two moves cost the Rams two 1st round picks, a 2nd round pick, two 3rd round picks, and two late-round picks, as well as pass rusher Jared Verse. All of that has rewarded L.A. with a 3-4 record and a distant third place in their own division.

Ryan Poles is not a win-now guy.

That is to say, he’s never been a big believer in “all-in” moves. He believes in building through the draft, maintaining a steady stream of young, cheap talent on the roster. The goal is to stay competitive over the long term. It is difficult to do that when you give up valuable assets in trades for players who may have three good years left at most. Much of this hinges on how confident Ryan Poles is in this team’s ability to win a Super Bowl. They certainly have the offense. Quarterback Caleb Williams and head coach Ben Johnson have that unit humming.

It comes down to the defense. Would one bold move transform that unit into something genuinely formidable? That depends on who you ask. Some feel the addition of a Jeffery Simmons or Maxx Crosby would change everything. Others think the problems with the unit go beyond just one position.

Resources play a part in this decision.

Right now, the Bears have all of their picks in 2027. However, they don’t have anything extra. That means if they decide to swing a deal, they will have fewer selections than normal. That makes building through the draft much more difficult. It drastically decreases your margin of error. Is Poles confident he can still make it work like that? If so, then a trade is viable. If not, don’t expect much to happen.

Here’s what we know. Throughout his tenure, Poles has never given up a 1st-round pick for a player. That means you’re likely looking at a 2nd-round pick at most. The said player would have to be under 30, probably between 26 and 28. That limits the market somewhat. Still, there are good options out there. It comes down to whether Poles can negotiate well enough to persuade teams to turn down potentially better offers. We’ll have an answer to these questions by next week.

The Chicago Bears sound like they plan to be active at the trade deadline this year. Unfortunately, that doesn’t tell us much about how aggressive they’re planning to be. There are many different levels to being “active” in something like this. You can flip a late round pick to another team for a player and call it active. Or you can put together a blockbuster package for a star and be called the same. The tricky part is determining what level of aggression the Bears are prepared to be.

After researching past deadlines, I’ve determined there are four levels. Rather than bore you with numerical values, I decided to use baseball analogies to help illustrate them. Based on the available information about possible targets, one tier stands out above the rest.

Chicago Bears trade option #1 – The bunt

This is the type of trade that Ryan Poles has done a few times at the deadline in recent years. It’s a trade for somebody who can serve less as a difference-maker and more as quality depth at ailing positions. A perfect example was last year when the Bears sent a 6th round pick to Cleveland for Joe Tryon-Shoyinka. It gave them some help on the back end, but ultimately didn’t move the needle much.

Potential options at this level:

• CB Nahshon Wright
• CB Donte Jackson
• DT Adetomiwa Adebawore
• EDGE Josh Uche
• DT David Onyemota

Trade option #2 – The single

These are your bargain trades for one of two types of players: an older veteran who still has some gas in the tank or a player who another coaching staff may have just misused. You saw two examples of this last year with Joe Thuney and Jonah Jackson. Chicago gave up 4th and 6th round picks, respectively, for the two men, and they quickly became anchors on the offensive line. That is the high-end you can expect from cheaper trades.

Potential options at this level:

• EDGE Khalil Mack
• DT Daron Payne
• DT Zach Sieler
• CB Tariq Woolen
• S Budda Baker
• EDGE Carl Granderson

Trade option #3 – The double

These are the trades where a GM is willing to get a little aggressive. We’re talking a 2nd or 3rd round pick and change to acquire a player of considerable renown. Poles has done two of them in his time as general manager. The first was for Chase Claypool in 2022 and the second was for Montez Sweat in 2023. The first was a complete disaster. Thankfully, the one for Sweat turned out pretty well for the Chicago Bears.

Potential options at this level:

• EDGE Josh Sweat
• EDGE Chase Young
• EDGE Will McDonald
• EDGE Chop Robinson
• DT Moro Ojomo
• DT DeForest Buckner
• CB Zyon McCollum
• CB Juju Brents

Trade option #4 – The home run

This is the big-game hunting tier—the select few players who will likely command a 1st round pick to acquire. To date, the Bears have never made one this big. They’ve flirted with the idea once or twice, but never got serious. Is this finally the year that changes? The Rams traded for Jalen Ramsey in 2019. San Francisco nabbed Christian McCaffrey in 2022. There are examples of these big swings paying off. If the Bears feel like they’re close, this might be the time to do it.

Potential options at this level:

• DT Jeffery Simmons
• EDGE Maxx Crosby

Chicago Bears general manager Ryan Poles has seen several bitrade opportunities pass him by over the past three years. He hasn’t made any move that could be categorized as “big” since the blockbuster in 2023 that landed D.J. Moore and the eventual 1st round pick that secured Caleb Williams. Ever since then, it’s been mostly moves involving later picks for established veterans. Granted, he’s still finding great value with this approach, as Joe Thuney and Jonah Jackson have proven. Still, it feels like Poles is due for some sort of big swing.

Yet based on most of the rumors lately, you shouldn’t bank on that happening for the upcoming trade deadline. The names connected to the Bears in the past couple of weeks include Khalil Mack and Nahshon Wright. Both are unlikely to cost more than a mid-to-late round pick. However, insider Jordan Schultz recently reported that the two teams generating the most noise as the deadline approaches are the San Francisco 49ers and the Bears. This would suggest that Poles might be planning something big.

Is Ryan Poles using the media to run a smokescreen?

Let’s not act like this isn’t something professional teams do. Using the media to manipulate the information you want circulating is a time-honored tradition in sports. Poles has demonstrated an ability to do this on several occasions. A good example came in 2025. Everybody thought the Bears would target a left tackle or tight end, Tyler Warren, with their 10th overall pick. Instead, they snapped up Colston Loveland, much to the annoyance of several teams that were hoping he’d drop.

Just think about it. Ryan Poles understands the situation. Mack and Wright are two names Bears fans love. They are certain to drum up all sorts of media buzz if both were connected to the team via trade rumors. While everybody is focused on that, he would be free to conduct business elsewhere without worry about drawing too much attention. Mack and Wright would help the team’s depth concerns. However, neither can be called true difference-makers. It feels like the Bears should be in the market for one of those.

Poles has some fascinating options in play.

The name that is rapidly gaining the most steam is DeForest Buckner. Despite being in his 30s, the defensive tackle remains a constant pain for opposing offensive lines. He’s clearly not happy with his situation in Indianapolis as the Colts keep fading. Adding him in the middle would be a great short-term boost. Of course, there is also Maxx Crosby. His availability looked dead after the Las Vegas Raiders started 3-0. They have since lost four in a row and are spiraling down the drain. He could be back on the table with another loss next week.

Probably the biggest fish, though, is Jeffery Simmons. The 29-year-old defensive tackle is wrecking the competition again this season with 4 sacks in 7 games. There is every reason to think he can probably keep this up at least a couple more years. His versatility as an interior pass rusher and run defender is nearly unrivaled. If ever there was a player who could instantly alter the landscape of the Bears’ defense, it’d be him. Will Poles be willing to pay the price?

The Chicago Bears are widely expected to be active at the trade deadline next month. They’re 5-2 and look like one of the better teams in the NFC. One strong move at the deadline could push them to the top of the heap. Either that, or they could make a couple of minor moves to bolster their depth at key positions. Most of the talk over the past few weeks has been around the edge rusher position. That is no surprise, as the team hasn’t gotten standout production from that group. It’s only gotten worse with injuries and suspensions hitting it. However, there is an almost equal problem at cornerback.

Jaylon Johnson has regressed significantly this season, looking like the worst of the team’s starters. Tyrique Stevenson has battled injuries, while Malik Muhammad is a rookie. It feels like the Bears need another option to freshen up the mix. While some notable names could be available, one that seems like an obvious choice is Nahshon Wright. The Pro Bowler had 5 interceptions last season with Chicago, opting to sign a $3.5 million deal with the New York Jets as a free agent. However, the team has barely played him this season.

It feels like he can be had on the market and won’t be expensive to acquire.

The Chicago Bears wouldn’t be done there.

Everybody has already heard the rumors surrounding Khalil Mack for weeks. Those were fanned even further by both Adam Schefter and Jay Glazer this weekend. It’s pretty clear the Bears are interested in bringing the former All-Pro back to the Windy City for one more round. It makes sense. He’s 35 and looking to play for a contender. They need more juice for their pass rush. It would be a mutually beneficial pairing. Mack has indicated on multiple occasions that he misses Chicago. Bears fans want him back.

It is far from crazy to think the team could bring both players back. Projections have Mack costing around a 5th round pick to acquire from the Los Angeles Chargers. Wright won’t have much of a market, so he’ll likely be gettable for a future 7th rounder. The Chicago Bears could add quality depth pieces to their defense for pennies on the dollar. Even better, defensive coordinator Dennis Allen worked with both players. He knows exactly what they can do and how to deploy them.

Much depends on how aggressive the Bears want to be.

General manager Ryan Poles hasn’t been afraid to take big swings in the past. The Montez Sweat trade is a big example there. However, in recent years, he has opted for a budgetary approach, flipping mid- and late-round picks for veterans who can bolster the team’s depth. This time could be different, though. The Bears have the look of a team that is a legitimate contender. When that happens, the logical approach is to try to give it one last shove forward with a front-line acquisition.

There are some big names out there who could be had. Maybe the Bears take another crack at Maxx Crosby. Jeffery Simmons seems like an obvious option as well. They’ll just have to pay a high price to get them. If Poles decides it’s too high, then he’d probably score points with fans by bringing Mack and Wright home, all without breaking the bank.

The story has been building for quite some time. Many felt Ozzy Trapilo was staring down a potential career-killing injury with that patellar tendon rupture this past January. There were real fears that he wouldn’t be able to return until 2027, leaving his future in doubt. So when he returned to Chicago Bears training camp in mid-August, it was considered a minor miracle. Not only was he back practicing, but there was a chance he’d reclaim his starting left tackle job long before anybody thought it’d be possible.

There is good news and bad news on that front. Trapilo has finally started logging snaps in actual games, playing 17 against the Atlanta Falcons and 19 against the New England Patriots. That tells you the Bears are putting more and more on his plate, gaining confidence in that knee. However, the bad news is that Trapilo might struggle to reclaim his spot.

It isn’t because he’s played terribly in his short stints. This is more because Theo Benedet has actually been playing well since taking over the starting job in week 4.

Ozzy Trapilo is running into a classic NFL problem.

That is the danger of having your spot taken out from under you. There is a reason NFL players fear getting injured. They know there are only so many starting jobs on a roster. If you’re not available to fill one, the team must find someone who can. Such circumstances can often lead to said replacement performing well enough that the team is reluctant to remove them, even when the original starter is healthy. The most famous example is when Tom Brady replaced Drew Bledsoe in 2001.

Such an event could be unfolding for Ozzy Trapilo. Benedet struggled a bit in his first start against the New York Jets, allowing 4 quarterback pressures. However, since then, he’s played better, allowing just 6 pressures in 3 games. He has also furthered his reputation as a solid run-blocker. Many felt the only reason Benedet couldn’t start was his pass-protection weakness. If the former undrafted free agent has solved that problem, then it might prove difficult for Trapilo to finish his redemption arc.

Chicago’s next game will likely decide a lot.

The Bears will go into the inhospitable home of the defending Super Bowl champion Seattle Seahawks. Their defense ranks among the league’s best, having just gotten done smothering the Kansas City Chiefs and Patrick Mahomes. Everybody saw what they did to Drake Maye in their two meetings with the Patriots between February and September. The only way you beat them is if the protection can hold up against that fierce defensive front. If Benedet crashes back down to earth, it would open the door for Trapilo to reclaim his job.

If he doesn’t? Then the team suddenly faces a controversy at left tackle, far different from the one they expected. It would be a tremendous accomplishment for Benedet, who’s fought through so much to reach this point. For Trapilo, it would be an obstacle he must overcome. The team hasn’t lost faith in him. He’ll just have to wait for the next opportunity.

If there is one thing you know about hot-button topics in the media, it is that they will always draw attention from people who hope to exploit them for personal gain—especially politicians. The Chicago Bears stadium issue has remained deadlocked for months as Illinois and Indiana wrestle for momentum. Illinois governor J.B. Pritzker seems more confident than ever that a deal is close to keep the team in its home state. This largely comes from recent meetings with NFL commissioner Roger Goodell and Bears minority owner Pat Ryan.

With the fall legislative session around the corner, there is real optimism that a bill everyone can be happy with will pass. One person not convinced of this is Pritzker’s GOP challenger for governor, Darren Bailey. He has insisted that the Democrats support policies that have been driving small businesses and the Bears to search for better homes out of state. Pritzker acts like he’s doing everything to keep the team when in reality, he’s done nothing. Bailey is clearly trying to drum up support from voters by making it sound like he will do everything in his power to keep the team in-state.

Unfortunately, this Chicago Bears stadium plea was exposed as a stunt.

Rick Pearson of the Chicago Tribune reported how Bailey, who tries to sound like a dedicated fan, could even name a single player on the team when asked. It was pretty ugly.

In an interview earlier this month with Mark Maxwell, a reporter for St. Louis’ KSDK-TV, Bailey was asked to name his favorite Bears player. The Republican candidate fumbled.

“Ah, it may be Staley. Staley the mascot came up, and we had a fun time with him on the opening day,” Bailey said, referencing his attendance at the Bears’ Sept. 20 home opener against the Minnesota Vikings. Asked again for a specific player, he cited the team that won the Super Bowl in January 1986 and the “days of Jay Cutler, the days of McMahon and currently, yeah, my mind’s blank. Is it Williams, No. 18?”

An important lesson was learned the hard way.

If you intend to use something for political gain, it might be a wise idea to study up on what you’re talking about. Watch a few games, or just read the depth chart a few times. Bailey couldn’t even be bothered to do that much. That isn’t a great look for someone who claims he’s fit to be the governor of an entire state. It is little wonder most people aren’t taking him seriously as a challenger to Pritzker. If he were, you’d have to think the Chicago Bears would’ve been talking to him about a potential deal. There has been no evidence of this since the midterm elections began.

Say this for the GOP in Indiana. They’ve handled the situation far better. While they’ve expressed confidence at every opportunity that the Bears will cross the border, they’ve never gone beyond that. They have tread carefully on a subject they know can be dangerous if not handled with care. Bailey comes across as a man desperate for attention. Diving headfirst into the Bears stadium situation felt like an obvious play. He never imagined how much it could backfire.

The path ahead is clear.

All signs point to the Bears making a strong push during the fall session to get a deal done. They seem to have finally built up some real support in Springfield with the right people. Putting Ryan in charge and benching Kevin Warren feels like the decision that kickstarted it. They finally have the right people leading the charge. Almost everything is in place to cross the finish line. All they have to do is collect enough votes in the House and Senate. With Pritzker’s backing, that should be possible.

Then again, it feels like they’ve been close before. If there is one fundamental truth about Illinois politics, it’s that things can fall apart remarkably fast because of constant infighting. The Bears clearly want to get something done soon.

Anybody who has been a fan of the Chicago Bears for any length of time knows one fundamental truth. The best player in franchise history was Walter Payton. That isn’t even up for a debate. He was probably the most popular athlete in Chicago sports history, not named Michael Jordan. We’re talking superhero status. Everybody looked up to him. It’s not an accident that the entire city went into mourning when he suddenly passed away in 1999. Since then, nobody has really come close to that level of excellence and popularity. Brian Urlacher had a great run. Derrick Rose looked like a possibility before his knee injury. Then you have Caleb Williams.

Quarterbacks haven’t exactly been the most popular people in this town for the past several decades. Most of that is because the majority of them weren’t very good. Those who were always had certain issues that made it hard to like them too much. Jay Cutler was too standoffish and turnover-prone. Mitch Trubisky was too inconsistent. Justin Fields lacked the natural instincts of a quarterback. Williams is the first to come along without those problems. Combine that with a fiercely competitive mentality, fiery persona, and ability to carry his team to wins, and it feels like he is the first to encroach on Payton’s territory.

It wasn’t a random fan or analyst saying this, mind you. It was Payton’s own son.

Caleb Williams is already putting together the necessary pieces.

What separated Payton from the other Bears greats was the ability to mix two things into one: superstar numbers and superhuman highlights. Every week, it felt like Sweetness was posting 150 yards on the ground, showcased by him running over two defenders and stiff-arming another into the bench area. Then he’d go do it again the next week. It made him appointment viewing for Bears fans, especially during an era where the team had been really bad for a long time. Many felt he was the catalyst for the team’s eventual turnaround into a contender by the mid-1980s.

It has been much the same way with Caleb Williams. You have to remember the quarterback arrived at a time when the organization was in one of the worst ruts in franchise history. Between 2013 and 2024, they had a winning season just one time. It was a miserable era of Bears football that some feared would never get better. Williams made it his mission to change that. In 2025, he engineered seven 4th quarter comebacks while leading the Bears to an 11-6 record and their first division title in seven years. He did this while also beating the Green Bay Packers twice.

Nothing earns the love of fans in this city faster than that.

The objective is pretty clear.

Payton cemented his place at the top of this city with two major accomplishments: he claimed the NFL’s all-time rushing record and helped win the team’s only Super Bowl. That is pretty much what Williams must set out to accomplish. Put up big numbers, win a lot of games, and bring home some Lombardi trophies. Simple? Sure. Easy? Not at all. Payton put his body through years of physical torture to accomplish that. Williams is quickly realizing he will have to do the same.

The good news is he’s starting to get some real help around him. Head coach Ben Johnson’s arrival gave him one of the best offensive minds in the business. The talent on the roster has significantly improved over the past year. Everybody saw what Payton could do once surrounded by help. It’s been the same with Williams. The craziest part is that he could do even more since he’s a quarterback.