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K-olson Montgomery and the Strangest 30-Homer Season in MLB History

Sep 27, 2026; Chicago, Illinois, USA; Chicago White Sox shortstop Colson Montgomery (12) reacts after striking out during the eighth inning against the Colorado Rockies at Rate Field. Mandatory Credit: Matt Marton-Imagn Images

There are MLB records you dream about breaking. Then there’s the one Colson Montgomery claimed. The Chicago White Sox infielder now stands alone as the MLB’s single-season strikeout king, passing Mark Reynolds’ 2009 record of 223 with 227 strikeouts in 638 plate appearances.

Despite modest expectations surrounding the White Sox entering the season, Montgomery has been a major reason they are heading to the Wild Card round. Chicago’s offense ranked first in the American League and second in MLB with 776 runs scored, and Montgomery was one of its biggest contributors. He ranked second on the team with 87 RBIs and fifth with 71 runs scored, accounting for over  15% of Chicago’s offense.

Most of that damage was done via the long ball. The White Sox ranked fifth in the MLB with 211 homers, and Montgomery accounts for 31 of them, the third most on the team behind only Munetaka Murakami and Miguel Vargas. 

Yet for all the damage he did at the plate, Montgomery finished the regular season with a modest .685 OPS. Among the 1,408 players in MLB history to hit at least 30 home runs in a season, Montgomery’s 2026 campaign ranks 1,407th in OPS,  with only one season posting a lower mark.

The culprit was a brutal second half for Montgomery. After posting the fifth-highest WAR among shortstops through his first 31 games, Montgomery hit just .163/.253/.304 with eight home runs, 34 RBIs and 106 strikeouts over his final 62 games. His struggles reached a boiling point in September, when he slashed .099/.215/.210 with two home runs, 10 RBIs and 42 strikeouts in the final month of the season.

The lack of production from one of the team’s biggest impact bats played a role in the White Sox coughing up their division lead and ultimately finishing just one game short of the No. 2 seed in the American League and a first-round bye.

Of course, it’s unfair to put the blame solely on Montgomery’s shoulders. While he became a liability at the plate down the stretch, he remained one of the team’s most valuable defenders at shortstop. His Fielding Run Value ranked in MLB’s 93rd percentile, while his 13 Outs Above Average ranked in the top 3% of the league.

Now, on the eve of the White Sox’s first postseason game since 2021, Montgomery has a chance to reset. If Chicago hopes to make a deep October run, it will need Montgomery to rediscover the bat that made him one of the team’s most important offensive pieces earlier in the season.

Plenty of power hitters have swing-and-miss issues. In an era when pitchers are throwing harder than ever and teams can turn to bullpens filled with specialized weapons, a high strikeout rate comes with the territory.

But there’s an important distinction between Montgomery and most of the hitters who fit that mold. The players who have struck out at a rate comparable to Montgomery have typically been true three-outcome hitters, capable of offsetting their strikeouts by getting on base. 

Before Montgomery’s record-setting strikeout season, the five highest single-season strikeout totals in MLB history were:

  • Mark Reynolds (2009): 223 strikeouts, 44 home runs, .349 OBP, .892 OPS
  • Adam Dunn (2012): 222 strikeouts, 41 home runs, .333 OBP, .800 OPS
  • James Wood (2025): 221 strikeouts, 31 home runs, .350 OBP, .825 OPS
  • Chris Davis (2016): 219 strikeouts, 38 home runs, .332 OBP, .792 OPS
  • Elly De La Cruz (2024): 218 strikeouts, 25 home runs, .339 OBP, .809 OPS

That hasn’t been the case with Montgomery, who finished the season with a .197 average, .282 OBP and a 35.6% strikeout rate, the highest in the MLB. 

While those struggles became even more pronounced over the final month of the season, the underlying issues followed Montgomery throughout the year. He walked in just 8% of his plate appearances, largely because of his inability to lay off pitches outside the strike zone. His chase rate and in-zone contact rate both ranked well below league average, limiting his ability to work deep into counts. He also routinely put himself in unfavorable counts with a first-pitch swing rate 14% higher than the MLB average.

Montgomery has never been one to hit for a high average and has always had a tendency to chase pitches out of the zone.  But during his rookie season, he punished strikes when pitchers challenged him. Much of his production last season came when he pulled balls in the air, and his 27.2% pull rate on airborne contact ranked among the highest in baseball. 

However, as pitchers adjusted to Montgomery, he struggled to counter those adjustments. He still possesses one of the fastest bat speeds in MLB and generates a high barrel rate when he does make contact. The problem is that he simply doesn’t make enough contact in the first place.

That became especially costly in high-leverage situations, where Montgomery struggled to turn his raw power into production. With runners in scoring position, he hit just .169 while striking out 77 times, making it difficult for the White Sox to consistently rely on him in their biggest offensive moments.

But none of that will matter if Montgomery can flip the script in October. One strong postseason could quickly change the conversation surrounding his season.

The longer-term question is where Montgomery fits into the White Sox’s plans. It’s rare to find a shortstop who can provide Gold Glove-caliber defense while also hitting 30-plus home runs. But Chicago has a crowded infield picture developing behind him.

Roch Cholowsky and Caleb Bonemer are waiting in the wings, while Sam Antonacci doesn’t appear to be a long-term fit in left field. Chase Meidroth has looked like the real deal at second base, and Miguel Vargas has developed into one of the game’s best third basemen. That leaves Chicago with a deep group of infielders and only so many spots to fill.

Herb Brooks famously said, “Great moments are born from great opportunity.” Montgomery has one in front of him this week,  a chance to remind everyone why the White Sox once viewed him as a cornerstone of the franchise.

Fair Or Not: Why Monday Night Is A Must-Win For The Chicago Bears’ Backup QBs

chicago bears
Aug 15, 2026; Chicago, Illinois, USA; Chicago Bears quarterback Case Keenum (11) passes the ball against the Cleveland Browns during the second half at Soldier Field. Mandatory Credit: Patrick Gorski-Imagn Images

Case Keenum will get the start tonight against the Philadelphia Eagles. It marks the first time since 2023 that a Chicago Bears backup quarterback saw playing time. It’s been a rare treat having a starter under center for two consecutive seasons. Alas, all good things come to an end. A hamstring injury has knocked Caleb Williams out. It appears he is likely to miss up to a month. That means it falls to Keenum and Tyson Bagent to carry the banner until he gets back. What isn’t known at this point is how successful they must be.

Unsurprisingly, it looks like the NFC North will be a dogfight once again this season. Minnesota leads the way at 3-0 while Detroit is 2-1. Dropping to 1-2 feels like a pretty deep hole for the Bears to climb out of. You never want to say your third game of the season is must-win, but it feels like this one is important. It’s a lot to ask of backup quarterbacks who didn’t get many reps in training camp. That led me to an interesting question.

How good must a backup be to give his team a reasonable chance to make the playoffs?

To answer this, I went back over the past five seasons, looking for every instance where a backup came in for an injured starter and played 4 or more games. I then pinpointed their win-loss record and whether the team reached the postseason. The results were not encouraging.

The Chicago Bears may need more than treading water.

SeasonBackup QBNFL TeamInjury to StarterStarting Record in StretchMade Playoffs?
2025Gardner MinshewLas Vegas RaidersAidan O’Connell (Thumb)2–7No
2024Cooper RushDallas CowboysDak Prescott (Hamstring)4–4No
2024Mason RudolphTennessee TitansWill Levis (Shoulder)1–4No
2024Spencer RattlerNew Orleans SaintsDerek Carr (Oblique)0–4No
2023Gardner MinshewIndianapolis ColtsAnthony Richardson (Shoulder)7–6No
2023Jake BrowningCincinnati BengalsJoe Burrow (Wrist)4–3No
2023Tommy DeVitoNew York GiantsDaniel Jones (ACL)3–3No
2023Joe FlaccoCleveland BrownsDeshaun Watson (Shoulder)4–1Yes
2023Joshua DobbsMinnesota VikingsKirk Cousins (Achilles)2–2No
2023Nick MullensMinnesota VikingsKirk Cousins (Achilles)0–4No
2023Tyson BagentChicago BearsJustin Fields (Thumb)2–2No
2023Easton StickLos Angeles ChargersJustin Herbert (Finger)0–4No
2022Brock PurdySan Francisco 49ersJimmy Garoppolo (Foot)5–0Yes
2022Taylor HeinickeWashington CommandersCarson Wentz (Finger)5–3–1No
2022Sam DarnoldCarolina PanthersBaker Mayfield (Ankle)4–2No
2021Tyler HuntleyBaltimore RavensLamar Jackson (Ankle)1–3No
2021Trevor SiemianNew Orleans SaintsJameis Winston (ACL)0–4No
2021Taysom HillNew Orleans SaintsJameis Winston (ACL)4–1No
2021Davis MillsHouston TexansTyrod Taylor (Hamstring)0–6No

Near perfection is needed.

As you can see, there were only two cases where a backup successfully helped his team reach the postseason. First was Brock Purdy in 2022 and then Joe Flacco in 2023. They went a combined 9-1 in their starts. Anybody who lost two or more games failed to get it done. Taysom Hill might’ve joined them if not for a midseason injury that delayed his taking over as the starter for a few weeks. The New Orleans Saints finished 9-8, just missing the playoffs. That shows you how slim the margin of error is.

The Chicago Bears don’t need Keenum and Bagent to be electric on the stat sheet. They need them to find a way to win. That means playing offense efficiently, staying on schedule, scoring at every opportunity, and avoiding turnovers. It won’t be just on them. This must be a complete team effort. The running game must be the driving force of the offense, and the defense can’t afford one of its occasional letdowns where they allow 30+ points. Williams won’t be there to rescue them like last year.

There is some good news.

This is a situation Keenum has been in before. He was thrust into the lineup by an injury to Sam Bradford in 2017 with the Minnesota Vikings. Keenum went 11-3 and got them to the NFC Championship. Granted, he got lots of help from the NFL’s #1 defense, but the fact remains that he did his job. He understands what his responsibility is. Don’t be a hero. Be the responsible driver of a high-performance vehicle. Hall of Fame tight end Shannon Sharpe put it best to Bubby Brister with the Denver Broncos when John Elway got hurt in 1998.

“This is a Ferrari. As long as you don’t strip the gears or burn out the clutch, we’re going to be fine. Keep it in first, let’s go.”

Brister went 4-0. Denver finished 14-2, claimed homefield advantage in the playoffs, and won their second straight Super Bowl. He had 10 TDs and 3 interceptions in those four games. Just solid, efficient play. That is the example Keenum and Bagent must follow. Thankfully, they have head coach Ben Johnson to help them. His play calling prowess should make their lives a little bit easier in what is probably the most crucial stretch of the season.

Why Case Keenum Won’t Be In Awe Of Vic Fangio And That Eagles Defense

case keenum
Dec 31, 2017; Minneapolis, MN, USA; Minnesota Vikings quarterback Case Keenum (7) under center in the first quarter against the Chicago Bears at U.S. Bank Stadium. Mandatory Credit: Brad Rempel-USA TODAY Sports

Tyson Bagent looks like he’s nearing a return just in time for Monday Night Football. However, Jay Glazer of FOX Sports indicated that the Chicago Bears‘ plan is still to start Case Keenum. The primary reasoning is simple. They feel Bagent didn’t get enough work learning the game plan this week. Add his concussion issues on top of that, and it just feels more sensible to go with Keenum. His experience should be a considerable benefit in keeping the offense from getting too far out of sync.

There could be another factor. Keenum has had decent success going against Vic Fangio. The Philadelphia Eagles’ defensive coordinator has been among the NFL’s best for a long time. His unit was the primary reason that the team won a Super Bowl two years ago. It’s still as dangerous as ever. Keenum would know. He has gone against it a few times in his career. As a starter, he has faced Fangio three times. Keenum is 3-0 in those contests, completing over 71% of his passes with 3 touchdowns and no interceptions.

DateMatchupGame ResultCmp / AttCmp %Passing YdsTD / INT
Oct 9, 2017MIN @ CHIW 20–1717 / 2181.0%1401 / 0
Dec 31, 2017MIN vs. CHIW 23–1021 / 2972.4%1891 / 0
Oct 21, 2021CLE vs. DENW 17–1421 / 3363.6%1991 / 0
Total3-059 / 8371.1%5283 / 0

Case Keenum understands his job going against Fangio.

Efficiency is the name of the game. It is highly unlikely that he will be able to put up significant numbers. Few can. The goal must be to stay ahead of the sticks, distribute the ball, and avoid turnovers. He accomplished that objective in each of those three games. The game plan was the same every time. Manage the game, run the ball, and hope the defense gives you some support. Fortunately, Keenum got it in all three. His offenses averaged 162 yards on the ground across all three contests.

You can bet the Bears hope to duplicate this strategy on Monday night. They’re equipped to do so. Johnson’s system is geared toward running the ball, and they have the pieces in place. Philadelphia is only 23rd in the league against the run. Case Keenum understands how to adhere to a run-first game plan. He does it quite well. Victory is not guaranteed for the Bears. Still, they’re at least fielding a quarterback who understands the challenge ahead of him and has experience dealing with it.

Will it be enough?

That depends entirely on which Bears team shows up. If they arrive with urgency, this is a game they can still win. They’re at home. They are equipped to attack the Eagles’ biggest weaknesses. If they can just avoid the costly mistakes they made last week, this should be a game they can steal. On the other hand, if they let the Eagles set the tone early, it can just as easily get away from them. This is one of those games where we’ll see just how good a coach Johnson is.

Keenum has been here before. He’s been thrust into a situation where he had to replace a former #1 overall pick and try to keep the train on the tracks. It worked out then. Maybe it can again. The Bears have the utmost confidence in him. Maybe there’s some magic left in that old body for one more upset. Doing it against Fangio would be rather fitting.

We Finally Know The Mystery Behind Caleb Williams’ Injury “Overreaction”

caleb williams
Bears quarterback Caleb Williams was carted to the locker room after an injury vs. the Vikings.

Caleb Williams went down with nobody around him last week against Minnesota. Many feared he might have suffered a season-ending injury. Based on his emotional reaction, including screams and needing help to get to the locker room on a cart, it didn’t look great. Then reports began filtering out that the Chicago Bears‘ quarterback had suffered a hamstring strain. Some former players and other analysts were puzzled. That seemed like a pretty strong reaction to something as relatively minor as a hamstring issue.

Some took it as a sign that Williams was soft. Others thought he might be milking it for attention. As always, time tends to reveal the truth. Sure enough, reports soon emerged that Williams had suffered a Grade 2 strain. However, it came with an added layer. The hamstring he pulled was the same one he injured in 2022 while with USC—that injury left behind considerable scar tissue. When the quarterback pulled it again on Sunday, that scar tissue essentially ripped apart. That is probably where the reaction came from. Such incidents are said to be excruciatingly painful. ESPN had the details.

“As for Williams, he injured the same hamstring in college. Last week, the third-year star went down without contact in severe pain and was eventually carted off in the fourth quarter of Chicago’s 9-3 loss to the Minnesota Vikings.

One reason for the pain was that Williams likely felt scar tissue breaking up from a past hamstring injury, a phenomenon that can be quite painful to experience but doesn’t lead to long-term damage.”

This is why Caleb Williams doesn’t listen to haters.

They don’t know anything about him. All of these fake tough guys were dogging him for being emotional following the injury. It’s just a hamstring. Suck it up. Of course, they said it with zero context. They just thought it was a prima donna athlete being a drama queen despite significant evidence to the contrary. Williams endured 68 sacks in 2024 without missing a game. He took plenty of tough shots last year, too. He returned from that nasty hamstring injury in college as well, despite no real incentive to do so. USC was out of the national title race by that point.

This guy is a competitor. What you saw on that wet field last Sunday wasn’t a guy being overdramatic. It was a human being suffering an incredibly painful injury that likely made him fear his season might be over. We all heard the stories of how hard Caleb Williams worked this offseason. He was dialed in on everything. The quarterback was determined to take this team to the next level. Put yourself in his shoes and imagine having it all ripped away from you because of a freak injury.

You probably would’ve cried too.

The path ahead is pretty clear, at least.

Williams’ injury will require 3-4 weeks to heal. Knowing how the quarterback thinks, he will absolutely try to be back before then. He has never missed games in his life. This is a new experience for him, and likely won’t be one he likes. Much will depend on how the Bears’ training staff handles the process. They’ve had bad experiences letting players back earlier than expected. It happened with Jaylon Johnson last year, who almost immediately tore his core muscle off the pelvic bone. This is probably why they don’t seem to be in a rush to get Ozzy Trapilo back on the field, despite his practicing in full.

If Williams is determined to get back for the Green Bay game two weeks from now, he’ll have to go through a rigorous rehab process and do everything short of sweet-talking everybody in the building to get out there. The guys in charge of this team typically have their eyes on the big picture. The last thing they want to for their quarterback to make a tricky injury worse by coming back too soon.

Latest Breece Hall News Gives Bears A Huge Opportunity If They Can Get Past The Eagles

breece hall
Sep 27, 2026; Detroit, Michigan, USA; New York Jets running back Breece Hall (20) is helped off the field during the game against the Detroit Lions at Ford Field. Mandatory Credit: David Reginek-Imagn Images

The Chicago Bears won’t have Caleb Williams’ magic for up to a month after the news that he’d suffered a Grade 2 hamstring strain. That means their season’s fate is in the hands of backups Case Keenum and Tyson Bagent. It is not a great situation to be in. To somehow stay alive moving forward, they will need a mixture of great execution from the rest of the roster and a stroke (or two) of good fortune in the coming weeks. It’s possible the Bears may have gotten one of the latter already via some alarming Breece Hall news.

Chicago plays the New York Jets next week. Hall has been their best offensive player for quite some time. He was off to a good start again in 2026, amassing 210 total yards and a touchdown in his first two games. Then things went sideways in week 3 against the Detroit Lions. As the Jets were driving deep into Detroit territory, Hall was tackled along the sideline. He seemed to go down awkwardly and failed to get up. He was quickly taken to the locker room and declared out for the rest of the game with a thigh injury.

Losing Breece Hall is a gut punch for New York.

Their running game was already suspect this season even with him. Hall averaged 3.4 yards going into that Lions game. His backfield teammate was even worse. Braelon Allen managed just 3.1 yards. This doesn’t even account for Hall’s impact in the passing game. He was 3rd on the team in receptions with 7. There is a reason the Jets worked hard to extend his contract. Given how it looked when he went down and how fast he was declared out? This feels like it was a quad injury.

A pretty serious one, too.

He is all but certain to miss next week when New York visits Chicago. Probably more with how rough it looked. This presents a premium opportunity for the Bears. If they can somehow upset the Philadelphia Eagles on Monday night to reach 2-1, their odds of beating the Jets are considerably better. Remember, their run defense has been a big problem to start the year. With Breece Hall out of the picture, that becomes less of a concern. Chicago could take advantage to reach 3-1 with two wins coming without Williams in the lineup.

At the very least, this improves the chances of avoiding 1-3.

Presuming the popular prediction holds true, and the Eagles prevail, the Bears would go into a must-win situation next Sunday at 1-2. While the Jets don’t seem nearly as bad as they were last year, they still aren’t a good football team. They are beatable. Head coach Ben Johnson knows Aaron Glenn’s defense well. He should be able to manufacture some points in that game. Responding becomes much tougher for the Jets without Hall. The NFL is all about seizing advantages when they present themselves.

Everything starts with Monday night. The Bears know people are doubting them. Par for the course when starting a third-string quarterback. If they want to show everybody that they’re not a one-person team, this is the time to do it. Philadelphia is good, but they’re not infallible. With the right game plans, they’ve proven to be vulnerable this season. If Chicago can pull it off, so many things open up for them.

AL Wild Card Playoff Preview: White Sox vs. Rangers

Jul 20, 2026; Arlington, Texas, USA; Chicago White Sox pitcher Erick Fedde (47) and catcher Kyle Teel (8) make their way from the bullpen prior to a game against the Texas Rangers at Globe Life Field. Mandatory Credit: Raymond Carlin III-Imagn Images

Yesterday the White Sox were eliminated from winning the AL Central, as they lost 9-6 to the Colorado Rockies, while the Cleveland Guardians took care of business against the Kansas City Royals. 

There are many, many games that you can look back at in the month of September that cost them the division, but fortunately they were able to still secure the third AL Wild Card spot. Unfortunately for the White Sox, the divisional win would have got them a bye and a chance to rest all their pitchers. Now, the White Sox will have a quick turnaround and play game 1 on the road on Tuesday. 

The White Sox will play the winner of the AL West, which will either be the Houston Astros or the Texas Rangers. Unfortunately for the Rangers, the Astros have the tiebreaker so they will need to win and Houston to lose to make it in. 

We will take a look to see how the White Sox fared against both potential opponents this season, as they played two series against each team. We now take a look at the potential matchup against the Texas Rangers.

Unlike the Astros, the White Sox had a winning record against the Rangers, winning both series they played against them. Despite the White Sox having a 4-2 record, there is a 0 run differential in the season series with each team blowing the other out a couple times.

First Series (July 20-22)

In the first game of the series, the White Sox scored 10 runs behind a solid start from Erick Fedde, as he threw four innings of three run ball. The bats were alive as they had 13 hits and they cruised to a solid victory.

Game two was quite different, as they were beaten 10-0. Noah Schultz gave up five runs over 3 innings and the bullpen behind him gave up the rest. The bats were quiet as they only had three hits.

In the final game of the series, the closest of the bunch, the White Sox were victorious by a score of 4-2. Anthony Kay had five innings of two run ball while the offense was supplied by Andrew Benintendi and Chase Meidroth, who both had two RBIs.

This was a weird series for the White Sox, as this was one of Noah Schultz’s last starts before he was sent down to the minor leagues. This was also the series where the White Sox lost Kyle Teel for the second time this season. Despite that, the White Sox were able to still take the series pretty easily.

Second Series (Aug 24-26)

In the first game of the second series, the Rangers blew out the White Sox 11-2. Jose Urquidy gave up 5 runs in just three innings and the offense mustered up just five hits, as the only runs came in on a Tristan Peters home run.

In the second game, the White Sox got their revenge, as they won 11-7. Anthony Kay and Jordan Hicks combined to give up 7 runs in the first 5 innings, but the offense had 14 hits and were backed by three hits each by Tristan Peters and Chase Meidroth.

In the rubber match, the White Sox put up 10 more runs, winning 10-4. Sean Burke walked 8 batters in just three innings, but he somehow managed to give up just two runs. The bats came alive as Tristan Peters added three more hits.

This was the Tristan Peters series, as he helped the offense score 23 runs over three games. The pitching was bad, but they still managed to win games. This was an impressive series win for the White Sox team.

Wild Card Outlook

The White Sox match up significantly better with the Rangers, as they were able to beat them in the regular season. While the Rangers have more playoff experience, I would still feel much more comfortable playing the Rangers than the Astros.

The Rangers have a veteran staff that could perform well in the playoffs, but they were hit around by the White Sox in the regular season. If that trend continues, I would imagine that the White Sox have the slight edge in the playoffs series.

Why Kalif Raymond Will Be Thrilled At The Latest Case Keenum News

kalif raymond
Sep 20, 2026; Chicago, Illinois, USA; Chicago Bears wide receiver Kalif Raymond (14) looks on during warmups before the game against the Minnesota Vikings at Soldier Field. Mandatory Credit: Matt Marton-Imagn Images

The Chicago Bears are now likely not to have Caleb Williams for the next three weeks as he deals with a grade 2 hamstring strain. That means Tyson Bagent and Case Keenum will have to carry the load moving forward. It remains uncertain which of them will start. For most of the week, it looked like Keenum was the guy. However, Bagent practiced in full on Saturday. That gives him a reasonable chance to get his first start since 2023. There isn’t a consensus on who it should be. However, if Kalif Raymond had his say, he would push for Keenum.

Lucky for him, it’s looking that way.

It’s easy to forget that Chicago’s third-string backup actually started 38 games between 2017 and 2019. He went 18-20. Though his stats weren’t anything special, he did enough to keep his teams afloat. One way this was accomplished was by doing the smart thing. Get the ball to your best players. Seven years ago, that was Terry McLaurin. In Denver the year prior, it was Emmanuel Sanders. During his magical run in Minnesota in 2017? It was Adam Thielein. What do all of those names have in common? They were their respective team’s primary slot receiver.

Kalif Raymond is filling that role now in Chicago.

It was a big reason why head coach Ben Johnson pushed to sign him. The Bears didn’t have a definitive presence in the slot last year. Instead, they used more of a committee approach with D.J. Moore, Olamide Zaccheaus, and Luther Burden. It didn’t always work well. To make this offense go, you need a dependable presence on the inside. It is why he leads the team in targets. That is likely to hit overdrive with Keenum. He is much more of a system guy, meaning he will run the plays as designed more often than not.

Coach Johnson has repeatedly said this offense tends to find the slot receiver a lot. There is no reason to believe that will change. Keenum will act as an extension of his will. While the quarterback will try to distribute the ball to multiple targets going forward, he has a practical mindset. Get the ball to the playmakers and let them do their thing. It worked pretty well at previous stops when he had actual help. There is no reason it shouldn’t this time around. Kalif Raymond is plenty capable of handling the workload.

The bigger question is whether this is the right decision.

While Raymond is a solid player, he is not the best weapon on this offense. That title belongs to Colston Loveland, with Luther Burden probably next on the list. Yet the Bears haven’t really done a great job getting either of them the football. One would think they hope to rectify that against the Philadelphia Eagles on Monday night. Unfortunately, the opportunities aren’t likely to be plentiful. This defense is one of the best in the league against the pass. One has to figure the Bears will focus on running the ball.

That is also why Raymond is the name to watch. He was the primary target against Carolina when Chicago ran the ball really well in week 1. His ability to move the chains and keep the offense ahead of the sticks is key to making such a game plan work. We already know Keenum won’t have any qualms looking that way. If you have him in your fantasy leagues, you’d best start him Monday night.

AL Wild Card Playoff Preview: White Sox vs. Astros

Sep 3, 2026; Houston, Texas, USA; Chicago White Sox first baseman Munetaka Murakami (5) and teammates stand for the national anthem before playing against the Houston Astros at Daikin Park. Mandatory Credit: Thomas Shea-Imagn Images

Yesterday the White Sox were eliminated from winning the AL Central, as they lost 9-6 to the Colorado Rockies, while the Cleveland Guardians took care of business against the Kansas City Royals. 

There are many, many games that you can look back at in the month of September that cost them the division, but fortunately they were able to still secure the third AL Wild Card spot. Unfortunately for the White Sox, the divisional win would have got them a bye and a chance to rest all their pitchers. Now, the White Sox will have a quick turnaround and play game 1 on the road on Tuesday. 

The White Sox will play the winner of the AL West, which will either be the Houston Astros or the Texas Rangers. Unfortunately for the Rangers, the Astros have the tiebreaker so they will need to win and Houston to lose to make it in. 

We will take a look to see how the White Sox fared against both potential opponents this season, as they played two series against each team. We will first take a look at Houston, the likely opponent come Tuesday. 

The White Sox played Houston seven times this year, with Houston taking the season series five games to two. Right off the bat, that isn’t a great sign for the White Sox, as even with the Astros struggling this year, they seem to have our number.

Despite the Astros winning 5 games in the series, they only had a +3 run differential, scoring three more runs than the White Sox. However, that is slightly inflated for the White Sox, as they did win one of the games 12-3.

First Series (July 24-26)

In the first game of the series, the White Sox had a 5-0 lead going into the 6th inning, with Davis Martin cruising. Unfortunately, it completely unraveled as he and Bryan Hudson combined to give up 8 runs in that inning, eventually dropping the game 9-5. This was a very winnable game that they completely blew. 

In game 2, Sean Burke cruised for 6 innings allowing just 2 earned runs. However, Hunter Brown of the Astros was better, as he had 7 scoreless and the White Sox dropped the game 4-1. 

In game 3, the bats came to life and the Sox scored 12 runs. They hit 5 homers with Munetaka Murakami hitting two of them. 

This was a series they should have won if they didn’t have a total collapse in the first game. But, the starting pitching was good for the most part and the bats were on for two out of the three games.

Second Series (August 31- September 3)

The White Sox then played a 4 game series with the Astros at the beginning of September, where they dropped the series 3-1.

In game 1, Anthony Kay gave up 6 runs and the bats were quiet outside of Colson Montgomery, as we dropped the game 6-3. 

In game 2, Sean Burke was masterful and threw 5 and 2/3rds innings of scoreless baseball, while Colson Montgomery and Randal Grichuk both had 2 RBIs, leading the Sox to a 5-1 victory. 

In game 3, they had just 3 hits and lost 2-0 despite a scoreless start from Davis Martin. 

In game 4, the Sox lost 6-2, as Luis Castillo gave up 6 runs in 4 innings, which never gave the Sox a chance to win the game. The Sox did have 7 hits, but they were only able to muster 2 runs. 

This series was right when the White Sox started to sputter in September. The pitching wasn’t good and the bats were quiet. As the month went on, those were both corrected, as the White Sox have played much better than they did earlier in the month.

Wild Card Outlook

Overall, the Astros took it to the White Sox this season and are definitely the harder matchup for the Sox. Hopefully the Rangers can pull it off and win the division, as they played much better against the Rangers.

On the bright side, Sean Burke has had 2 stellar starts and Davis Martin had one great and one collapse after 5 strong innings, which could bode well for two of the games in the series. If the White Sox want a chance at advancing, they are going to need everyone on their A game or this series could get ugly quick. 

Perhaps the biggest advantage the Astros have is their playoff experience. They have many players on their team with multiple World Series appearances, while the White Sox have just a few players who have even played in the postseason. If they can limit the damage from Yordan Alvarez and take good at-bats, they’ll have a chance, but that may be a tough task to do.

The Caleb Williams Injury Was Worse Than Expected And What It Means

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Sep 20, 2026; Chicago, Illinois, USA; Chicago Bears quarterback Caleb Williams (18) is helped off the field with an apparent injury against the Minnesota Vikings during the second half at Soldier Field. Mandatory Credit: Patrick Gorski-Imagn Images

The Chicago Bears initially feared they may have lost Caleb Williams for the season after watching him go down against the Minnesota Vikings. Thankfully, the young quarterback avoided a disastrous injury, such as an Achilles or ACL tear. Tests eventually revealed that Williams had suffered a hamstring injury. That was not season-ending by any stretch. The only uncertainty was how severe it was. After some time, information came out that it was likely a Grade 1 strain. This meant that Williams could be back as early as next week against the New York Jets.

It now appears that wasn’t the case. ESPN reported on Sunday that Williams had, in fact, suffered a Grade 2 strain. While not devastating, it does mean the quarterback is likely out longer than originally hoped. Such an injury usually causes players to miss 3 or 4 weeks of action. This means the Bears could be looking at up to a month of Tyson Bagent or Case Keenum. As much confidence as the team may have in those two, it is far from ideal for a team that has Super Bowl aspirations.

“Chicago Bears quarterback Caleb Williams has a Grade 2 hamstring injury that doctors consider a three-to-four-week injury, league sources told ESPN and NFL Network.

This doesn’t mean that Williams, who the Bears have touted as a quick healer, couldn’t return sooner than that timeline. It just means that doctors believe this normally is a three-to-four-week injury in most players, and that is the doctors’ best estimation of how long it could take Williams to recover.

The Bears officially ruled Williams out for their Week 3 game against the Philadelphia Eagles on Monday night, and have tried to keep the extent of his injury under wraps for competitive-purpose advantages.”

This Caleb Williams update brings everything into focus.

The Bears are now all but certain to play at least two games without Williams. Probably three. They faced the Philadelphia Eagles on Monday night. Then the New York Jets will come to town. By far the biggest one to watch will be the trip up to Green Bay for a grudge match with the Packers. If he misses that, then the extent of the injury will be pretty obvious. This is supposed to be one of the easier stretches of the schedule. Losing Williams at this time really hurt. Remember, they have both New England, Seattle, and Tampa Bay waiting for them before the bye week.

So what happens if Caleb Williams misses the full month? Looking at how daunting their second-half schedule is, they must find a way to at least stay at .500 during his absence. That means winning two of the next four games. Can it be done? Yes. While Bagent and Keenum are not Williams in terms of talent, this offense wasn’t designed to be quarterback-first. The Bears are a running team under head coach Ben Johnson. If they can pound the ball on the ground and get some solid performances from the defense, they can steal two games.

The vital key is that the Bears don’t beat themselves.

A huge reason they lost to Minnesota last week was a brutal series of self-inflicted wounds. They committed 8 penalties and 2 turnovers, giving the Vikings all the extra help they needed to pull off the win. Williams was good enough to overcome such setbacks. With him gone, it is more imperative than ever that the team play as efficiently as possible. Limit the penalties and don’t turn it over. A run-first approach should help with that. Johnson is unlikely to insist on Bagent avoiding aggressive throws. That isn’t how he’s wired. Still, it will be conveyed that he should not be reckless.

The game against Philadelphia will say a lot about this team. If they come out flat against the Eagles, it will not bode well for their chances to stay afloat long enough for Williams to return. They pride themselves on their mental toughness. Well, this is the biggest test they’ve faced in a long time. Johnson seems confident they can handle the challenge. The next four weeks will say a lot about his coaching ability.

Do The Bears Already Regret The Gervon Dexter Trade? Why They Might Be

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Sep 13, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Steelers offensive tackle Troy Fautanu (76) looks to block Atlanta Falcons defensive tackle Gervon Dexter Sr. during the secnd half at Acrisure Stadium. Mandatory Credit: Barry Reeger-Imagn Images

Most of the moves the Chicago Bears made this offseason at least made logical sense. They traded D.J. Moore because they couldn’t afford his contract and had young receivers ready for more targets. Tremaine Edmunds was released for largely the same reason. Kevin Byard, Jaquan Brisker, and C.J. Gardner-Johnson were allowed to hit free agency because they lacked the speed Dennis Allen wanted in his secondary. However, one move received widespread surprise and confusion. That was the Bears trading Gervon Dexter to the Atlanta Falcons.

Now it’s true that the team was unlikely to sign the defensive tackle to a contract extension. It would likely be over their budget, and he wasn’t a natural fit for Dennis Allen’s scheme anyway. Still, he was second on their team last season with 6 sacks and 43 pressures. Wouldn’t you want to keep that around another year, even if you know he’s leaving in free agency? The Bears didn’t like that idea. So they flipped him to Atlanta for cornerback Clark Phillips and a 5th round pick.

Three games into the season, and it looks like that was a regrettable decision.

Gervon Dexter is on pace for his best season.

Not only does he have 1 sack and 14 pressures in three games with the Falcons, but his 23.3 pass rush win percentage is the 4th-highest among all defensive linemen in the NFL. That is ahead of Maxx Crosby and even Dallas Turner. By contrast, the Bears’ defensive tackle unit has 7 pressures and 1 sack total in two games. That isn’t a great look, especially after Allen championed the team’s newfound depth at the position. Maybe part of the problem is giving Jordan Van Den Berg, your explosive new rookie, only 14 snaps. Or maybe it’s focusing too much on scheme fit and not enough on proven production.

Either way, Gervon Dexter is surging toward a significant payday next spring. Atlanta is projected to have more than $114 million in cap space. They are well-prepared to pay it. Based on what we’ve seen so far, Dexter is a key component to that Falcons defensive front—an ingredient they were missing. While the Bears do rank 5th overall in total pressures, they’ve mostly done so via the blitz. It is worth wondering how much better it might have been had they hung onto Dexter.

There is no time left for regrets.

The team clearly felt it had valid reasons for the change. Allen must’ve felt that he needed a specific type of defensive tackle to run his system properly. Still, it is hard to understand unloading good players when they helped you win the year before. Dexter did more than enough in 2025 to justify another season. Alas, the business of the NFL always gets in the way eventually. The Bears felt they had one of two avenues. Let Dexter play out his contract, or move him immediately for the best possible return.

They chose the latter.

It isn’t the first time a team has done this. It won’t be the last. The unfortunate truth is that the move doesn’t always yield positive results. Several teams likely wish they had just kept the player instead. Whether the Bears get a favorable return from this trade depends on whether the front office can get something from the 5th-round pick they received. That might be asking too much, considering Dexter was a 2nd round pick himself.