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Why Bengals Game Could Alter Caleb Williams’ Career Trajectory

caleb williams
Sep 14, 2025; Detroit, Michigan, USA; Chicago Bears quarterback Caleb Williams (18) passes the ball against the Detroit Lions during the first quarter of the game at Ford Field. Mandatory Credit: Lon Horwedel-Imagn Images

People have tried to stay patient with Caleb Williams, knowing the young quarterback was poorly handled by the previous Chicago Bears coaching staff last season. Undoing that damage would take time. Even so, it is difficult for many not to feel nervous about where his development is. After starting the season with seven touchdowns and one interception, he has two touchdowns and three interceptions over the previous three games. Williams hasn’t been a decisive presence on the field for weeks, which is not what you want to say about the quarterback you took #1 overall.

Some people might raise eyebrows at the idea that a game against the Cincinnati Bengals carries such importance. They’re an AFC team. It’s on the road and is unlikely to significantly impact the Bears’ playoff hopes either way. While that is true to an extent, one person should be very concerned about how this game goes. That is Williams. Cincinnati has the worst defense in football. They are 30th against the pass and 32nd in points allowed. Their best player, pass rusher Trey Hendrickson, is also unlikely to play. Everything lines up for Williams to have a big day in this game.

So imagine if he doesn’t. What happens if he struggles? There is a strong possibility that such a scenario could lead to some uncomfortable conversations inside Halas Hall.

Caleb Williams won’t get a better setup for success this season.

Cincinnati is being served up on a silver platter. Any competent quarterback would take full advantage. Unless the offensive line has a complete meltdown, which is unlikely, this is a game Caleb Williams should excel in. He doesn’t have to put up 400 yards and four touchdowns, but it’s not unreasonable to expect at least 250 yards and a couple of scores. If he can’t produce even that much, it will confirm many of the growing rumors about what is happening in that building.

People around the NFL have said it feels like Williams is resisting the instructions of head coach Ben Johnson. He’s still trying to play a similar style to his USC days, and it’s led to frustration from Johnson and others. Many have wondered how much patience the coach would have with his young quarterback, given his preference for playing on time and in rhythm. Another erratic afternoon against a defense like the Bengals’ might shift things in a direction Williams doesn’t want them to go.

Ex-Cubs Pitcher Returning from Dominant Stint in Japan

Feb 27, 2023; Salt River Pima-Maricopa, Arizona, USA; Chicago Cubs relief pitcher Anthony Kay (46) throws to the plate in the third inning of a spring training game against the Arizona Diamondbacks at Salt River Fields at Talking Stick. Mandatory Credit: Jayne Kamin-Oncea-USA TODAY Sports

Hey, remember Anthony Kay? Probably not as the left-hander pitched a total of 11.1 innings with the team in 2023, and his last handful of appearances were certainly forgettable, but now the 30-year-old looks like a decent free agent target heading into 2026 following his dominant stint in Japan.

Kay ended the 2023 season with the New York Mets after he was claimed off waivers in September. The lefty reliever was eventually scooped up by the Athletics in October, but elected free agency once the 2023-24 offseason began. Kay ended up in Japan, signing with the Yokohama DeNA BayStars.

In 2024, Kay recorded a 3.42 ERA in 136.2 innings. Not exactly Earth-shattering numbers as Kay returned to a starter’s role, but then his results drastically improved this past season as Kay posted a 1.74 ERA in 24 starts with a 21.5 K% and 57.8 GB%.

There’s obviously some familiarity between the Cubs and Kay, so we’ll keep an eye on any reports that may indicate interest in a reunion. Ultimately, Kay could end up being completely off the Cubs’ radar if he’s looking for another shot at being a starting pitcher in MLB.

Kay was a former top prospect for the Toronto Blue Jays, but he was never able to establish himself in the majors. The left-hander pitched in 28 games with the Blue Jays from 2019-22, including seven starts. Overall with Toronto, Kay posted a 5.48 ERA in 70.2 innings before the Cubs claimed him off waivers.

We’ll see if there’s any interest from the Cubs this offseason.

Anthony Kay’s 2023 Season with Cubs

The Chicago Cubs designated Anthony Kay for assignment to make room for Pete Crow-Armstrong late in the 20223 season, which officially ended the left-handed pitcher’s time in the organization. The New York Mets picked up Kay off waivers and assigned him to their Triple-A affiliate.

Kay, 28, made 13 appearances with the Cubs in 2023. The lefty was claimed him off waivers from the Toronto Blue Jays last offseason by the Cubs. Now, Kay is back with the Mets, the team who drafted him in the first round back in 2016 out of Connecticut.

The lefty competed for a bullpen spot in spring training and ultimately began the regular season in Triple-A. Kay was called up in June and made 13 relief appearances before he was optioned back down to the Iowa Cubs in August. He was fine in his first 10 appearances, posting a 1.13 ERA in 8 innings of work, but then 7 earned runs in his next 3.1 innings made his ERA balloon up to 6.35. Kay was briefly back up with the Cubs at the end of August, when right-hander reliever José Cuas went on the bereavement list.

In 30 games at Triple-A this season, Kay posted a 4.10 ERA in 37.1 innings.

Anthony Kay Career Summary

Kay, has pitched in parts of four seasons with the Blue Jays, getting his first shot in the big leagues back in 2019. Overall, the left-handed pitcher has appeared in 28 games at the major league level, making seven starts for Toronto. Kay has not been able to gain much traction in the show, posting a 5.48 ERA and 1.63 WHIP in 70.2 innings. In 2022, Kay only made one relief outing for the Blue Jays, allowing one run in two innings, against the New York Yankees early in April.

The lefty is a former first-round pick of the New York Mets, taken with the 31st overall (compensatory pick) in 2016. Kay did not pitch in the minors that year and in October 2016, he underwent Tommy John surgery, causing him to miss the entire 2017 minor league season. Kay finally pitched in the Mets organization in 2018, when he recorded a 4.26 ERA in 122.2 innings, making 23 starts in A-Ball.

In 2019, Kay had a breakout season, getting off to a strong start at Double-A. He had a 1.49 ERA in 12 starts before getting promoted up to Triple-A. Kay was named to the 2019 All-Star Futures Game in mid-July and then a couple weeks later he was traded from the Mets along with Simeon Woods Richardson to the Blue Jays for starting pitcher Marcus Stroman.

Kay finished the 2019 season making seven more starts at Triple-A in the Blue Jays system, posting a 2.50 ERA in 36 innings. Kay made his MLB debut on Sept. 7, 2019, starting against the Tampa Bay Rays, allowing two runs in 5.2 innings. He made a second start against the Yankees and had one final appearance out of the bullpen against the Baltimore Orioles.

In 2020, Kay had 13 relief outings, but struggled with a 5.14 ERA in 21 innings. He made five starts and six relief appearances for the Blue Jays in 2021, but once again had below average results with a 5.61 ERA in 33.2 innings. During the 2022 season, Kay tossed 21.1 innings in the minors, missing most of the year because of an injury.

Chicago Bears Were Out In Force To See Their Likely 1st Round Pick Next Year

chicago bears
Ohio State Buckeyes defensive end Kenyatta Jackson Jr. (97) celebrates during the NCAA football game against the Penn State Nittany Lions at Ohio Stadium in Columbus on Nov. 1, 2025.

There is no way to know for sure who a team will draft months before the event happens. So many things have to go a certain way. There are too many variables. Yet, from observing how the Chicago Bears have operated and identifying their needs going into 2026, it isn’t difficult to surmise who they might target next spring. Here’s a recap of what we know.

  • The Bears pass rush is one of the worst in the NFL
  • Their edge rush situation is weak outside of Montez Sweat
  • Dennis Allen prefers bigger defensive ends for his system

Factor all of these things in, and then add their persistent presence at Ohio State games and you start to see who they’re probably looking at. Multiple scouts attended the Penn State game this weekend, and the timing felt perfect, as it was a breakout performance for Kenyatta Jackson. The 6’6, 265-lb defensive end had two sacks and two tackles for a loss in a 38-14 drubbing of the Nittany Lions. He now has 4.5 sacks in his last five games, all against Big Ten opponents. If ever there was a specific player that screamed “Bears!” in this class, it’s him.

The Chicago Bears better hope Jackson’s tear doesn’t get out of control.

If he does too well, there is a strong chance the Ohio State standout could vault himself all the way into the top 10. Right now, the Chicago Bears are nowhere close to picking in that range. Initially, experts saw Jackson as a day two pick. While he possesses an abundance of physical talent, his production on the field wasn’t reflecting that. That has started changing. Players like him go early in the draft when they check both boxes. No doubt the Bears are hoping he stays under the radar just enough to give them a chance.

Then again, head coach Ben Johnson would probably prefer to make it irrelevant by getting to the playoffs. Such a scenario makes landing Jackson unlikely at this rate. Then again, he might get overshadowed by more hyped teammates, such as Caleb Downs, Arvel Reese, and Kayden McDonald.

The One Move Ryan Poles Will Regret Not Already Making

chicago bears
Oct 15, 2023; Chicago, Illinois, USA; Minnesota Vikings quarterback Kirk Cousins (8) is pressured by Chicago Bears defensive lineman DeMarcus Walker (95) in the first half at Soldier Field. Mandatory Credit: Jamie Sabau-USA TODAY Sports

The Chicago Bears defensive line is not in a good way. Their prized free agent addition, Dayo Odeyingbo, has one sack this season. Not exactly what the team hoped for after handing him $16 million a year. On top of that, Shemar Turner and Dominique Robinson are now out with lengthy injuries. The entire defensive front hasn’t been able to generate enough pressure on quarterbacks. While finding an instant solution is impossible this time of year, there is one possibility the Bears could’ve and should’ve explored already. It is surprising GM Ryan Poles hasn’t picked up the phone.

They must bring back DeMarcus Walker.

He is the one Chicago signed Odeyingbo to replace despite having a decent season last year, notching 3.5 sacks and 16 QB hits. One thing that was never misunderstood was his impact in the locker room. Walker was a vocal presence that others followed. It was hoped that Grady Jarrett could fill that void, but he’s been battling injuries. Now, as attrition takes hold, the Bears need help. Walker remains unsigned by any other teams. There is every reason for Poles to bring him back.

Ryan Poles must swallow his pride and bring Walker back.

The veteran defensive lineman would help with both of their key issues. He would give them a strong presence against the run on the edge, which Turner had handled. He’ll also provide versatility as a pass rusher. He certainly should be healthy and fresh, having spent months without a job. At 31 years old, there is no reason to think he is out of gas. It also won’t be expensive to sign him. There is literally no reason for Ryan Poles to justify avoiding this move any longer.

Chicago is in no position to be picky. They are unlikely to seek help on the trade market given their lack of draft capital to throw around. Salary cap space is almost in short supply. As helpful moves go, this is one of the few they can make. Walker knows the locker room and understands the role he’d be asked to play.

Price Tag For Breece Hall Revealed. Bears Could Be Involved

bears 2026 mock offseason
Sep 7, 2025; East Rutherford, New Jersey, USA; New York Jets running back Breece Hall (20) reacts to a play during the second half against the Pittsburgh Steelers at MetLife Stadium. Mandatory Credit: Wendell Cruz-Imagn Images

The Chicago Bears have kept any intentions regarding their trade deadline plans out of the national spotlight. Nobody has mentioned them to this point. This either means they’re not doing anything this year or they’ve kept their goals a closely guarded secret. One thing is clear. Injuries are mounting for them at several positions. Nobody would blame them for seeking help. Up until now, the discussions have centered on the defense, particularly edge rusher and cornerback. However, another position might get more action than people realize: running back. D’Andre Swift and Roschon Johnson are both injured, leaving their options limited. That is where Breece Hall comes in.

Despite the New York Jets continuing to be terrible, the 24-year-old is on pace for the best season of his career with 581 yards in eight games. With his contract expiring, many expect the Jets to trade him at the deadline. A new report revealed their price is a 3rd round pick. That seems high considering he’ll be a free agent. Still, his potential value to an offense would be high, and extending a running back is far less expensive than edge rushers or cornerbacks. Sources indicate that the Bears have been monitoring the situation for weeks and are interested.

The Bears can make Breece Hall happen.

As our colleague, Mr. Hughes, points out above, losing a 3rd round pick for Hall isn’t anything big. This organization has floundered in the 3rd round for years. Let’s recap Ryan Poles’ tenure.

  • Velus Jones
  • Zacch Pickens
  • Kiran Amegadjie

The first two names are already off the team. The other is injury-prone and unlikely to receive any playing time whenever he returns. Rather than continuing to throw away those picks, why not flip them for proven players? Breece Hall is certainly one of them. The only issue would be his contract.

Right now, the going rate for a top 10 running back in the NFL is around $10 million per year. Chicago can cut D’Andre Swift this offseason with only $1.3 million in dead cap. That would remove the largest running back contract from the books, allowing them to allocate the funds to Hall. This deal can happen. Everything depends on whether the Bears are willing to pay the price in draft capital.

Frustration Reportedly Mounting With Caleb Williams In Chicago

derek carr
Oct 13, 2025; Landover, Maryland, USA; Chicago Bears quarterback Caleb Williams (18) celebrates while leaving the field after the game against the Washington Commanders at Northwest Stadium. Mandatory Credit: Geoff Burke-Imagn Images

The Chicago Bears have done everything they can to help Caleb Williams. They’ve stacked the roster with capable players at every offensive position, from wide receiver to the offensive line and tight ends. More importantly, they brought in one of the best offensive minds in the NFL when they hired Ben Johnson as head coach. No Bears quarterback has enjoyed a better structure around him in the modern era. Yet for the first seven games of 2025, the results have been mixed. Johnson has offered no outward signs that he’s unhappy with Williams’ progress.

Yet as we’ve seen, that doesn’t always reflect the truth. Charles Robinson of Yahoo Sports generally has pretty good sources inside the league. He spoke on Insider Coverage about how frustration inside Halas Hall is building. Many feel Williams should’ve been further along in his development by now, yet he continues missing too many throws and isn’t taking full advantage of better protection or scheming. Meanwhile, other quarterbacks from his draft class haven’t had a problem playing well this season, particularly Drake Maye, who had a rough situation in New England last year.

@yahoosports

Inside Coverage on the Bears’ up-and-down season with their quarterback 😬 #calebwilliams #nfl #chicago #chicagobears #bears

♬ original sound – Yahoo Sports

SM sources confirmed the same about Caleb Williams.

In reality, this is something that has been building since the summer. Johnson didn’t like his quarterback’s lack of progress in training camp. The Bears head coach is a stickler for hitting the right pass at the right time. Caleb Williams, despite his individual talent, often turns down those opportunities. Apparently, this is why the Bears elected to extend Tyson Bagent. Remember, the backup signed his new two-year deal on August 20th, when camp was winding down. The timing felt somewhat odd. One would think they could’ve waited until later in the year. It seems Johnson made a strong push to ensure the Bears locked Bagent up as insurance in case things with Williams didn’t progress.

Does this mean the Bears are already looking for an exit? No. They remain committed to giving Williams every opportunity to keep growing. However, they need to see progress at some point. This Sunday in Cincinnati against a league-worst Bengals defense should be one such moment. If that team manages to keep Williams in check, that could result in some difficult conversations moving forward.

Bears Reportedly Sniffing Around Jaelan Phillips. Here’s The Likely Cost

jaelan phillips
Nov 5, 2023; Frankfurt, Germany; Miami Dolphins linebacker Jaelan Phillips (15) against the Kansas City Chiefs in the second half during an NFL International Series game at Deutsche Bank Park. Mandatory Credit: Kirby Lee-USA TODAY Sports

The Chicago Bears’ pass rush continues to be disappointing and has been since last season. Montez Sweat has at least regained some of his old form, but it’s not enough. All of their other edge rushers have underperformed, especially free agent addition Dayo Odeyingbo. Thankfully, Austin Booker has returned, which might help. However, he alone can’t be expected to solve everything. If this team wants to make a run, they need more from that front four. That is why the name Jaelan Phillips has emerged.

A source told SM that the Bears have kept close tabs on the former 1st round pick. As the Miami Dolphins flounder, many expect them to deal with him for draft capital to initiate a rebuilding process. GM Ryan Poles has a habit of targeting talented younger players. Phillips fits the profile. The obvious question is how much it will cost. Luckily, Dianna Russini provided an answer in her latest column for The Athletic. It is believed Miami is holding firm at a 3rd round pick. Would the Bears give that up?

Miami has received interest from the Eagles, 49ers, Patriots and others on OLB Jaelan Phillips (The Dolphins are looking for at least a third-rounder in return). They’re also getting calls on DE Bradley Chubb and OLB Matthew Judon.

Jaelan Phillips presents one big issue for the Bears.

That is his contract. This season is the last of his rookie deal. That means he is a free agent in 2026. Chicago would have three options on the table if they traded for him: extend him, franchise tag him, or let him walk. The tag is out of the question. That would saddle the Bears with a top five salary cap hit for next season, and they don’t have much cap space to work with. That means either they extend him or let him hit the market. The latter seems foolish because it would mean you gave up a 3rd round pick for what amounted to half a season of production.

That might be fine if you felt Jaelan Phillips was the last piece to a Super Bowl puzzle, but that is not the case for Chicago. Trading for him would require long-term planning. He’s 26, so keeping him around makes sense. The problem is that the Bears have already sunk a ton of money into their defensive line.

  • Montez Sweat – $25 million in 2026
  • Dayo Odeyingbo – $20.5 million in 2026
  • Grady Jarrett – $19 million in 2026

You can’t possibly add another player who will command at least $20 million per year—probably more. That means the Bears would have to unload one of those names. Cutting Odeyingbo or Jarrett with a post-June designation would saddle them with $17 million in dead money. That, along with some restructuring of other deals, could get it done, but that could hurt them down the road. It is a difficult knot to untangle.

We Found It. The Weirdest Chicago Bears Trade Rumor Just Surfaced

chicago bears
East Rutherford, NJ -- August 24, 2024 -- Evan Neal of the Giants before the game. The New York Giants and New York Jets meet at MetLife Stadium in the final preseason game of the 2024 season for both teams.

The NFL trade deadline is just three days away. Much of what happens for the Chicago Bears may be determined by the outcome of their game against the Cincinnati Bengals on Sunday. A win could compel them to make a move for some help. The lingering question is where? Most believe it would come somewhere on defense, either at cornerback or edge rusher. Both areas are decimated by injuries. However, the offense may also get some interest. The team has running back questions with D’Andre Swift now hurt. Their depth was always iffy.

It seems none of those directions is where Brad Gagnon of Bleacher Report sees it going. He believes the odds are favorable that the Bears will instead seek help on the offensive line, particularly at tackle. It’s well-documented that they have no definitive answer at left tackle. The solution? Well, take a look.

Chicago Bears: Acquire OL Evan Neal from the Giants

This after they already grabbed C.J. Gardner-Johnson on the open market. Braxton Jones is on injured reserve, while Theo Benedet has had issues at left tackle. Neal at least brings some experience and versatility, and the Bears can hope he gets a jolt in a new location, as the Giants have little reason to keep him around at this point. It’s insurance for a late-round pick at the very least.

Neal was New York’s 7th overall pick in 2022. He might be one of their biggest busts of the past quarter-century. In the previous three seasons, Neal allowed 12 sacks and 98 pressures in 1,157 snaps. It got so bad that the Giants moved him to guard this year, and he’s yet to play a single snap. The only argument to be made is he would get a chance to play left tackle, which was his original position in college.

The Chicago Bears don’t need another lost cause.

Nobody can pinpoint what went wrong with Neal in New York. He had tons of talent and had gotten great coaching at Alabama. Brian Daboll is a good offensive mind and understands how to develop linemen. Yet Neal was still a failure. The only explanation is that he never fully grasped how to make the switch to right tackle, which the Giants had asked him to do upon his arrival. Some blockers never develop the confidence when they move away from where they thrived in college.

If nothing else, such a trade would be dirt cheap for the Chicago Bears. They could probably land Neal for a late round pick in the 2027 draft without any issues. Even a pick swap is plausible. Much depends on whether head coach Ben Johnson or offensive line coach Dan Roushar believes there is anything salvageable. Braxton Jones just went on Injured Reserve, so that may open the door to something like this. Still, the odds are remote at best.

Analyst Fires Back At “Unfair” Caleb Williams-Drake Maye Comparisons

caleb williams
Sep 8, 2025; Chicago, Illinois, USA; Chicago Bears quarterback Caleb Williams (18) practices before the game against the Minnesota Vikings at Soldier Field. Mandatory Credit: David Banks-Imagn Images

Chicago Bears fans have seen this movie before. They took the first quarterback in a draft only to see somebody they could’ve had develop into a star. That was Mitch Trubisky going before Patrick Mahomes in 2017. Now it appears to be happening to them again, this time with Caleb Williams as fans watch Drake Maye thrive in New England. The bitter irony is that they took the wrong quarterback from North Carolina. The football gods have a sick sense of humor. Except one person is tired of hearing about it.

Matt Waldman of Football Guys is one of the most respected tape analysts in the industry. He has closely followed the 2024 quarterback class and has been aware of the developing narratives surrounding Williams and Maye. He is tired of hearing the slander towards the Bears’ quarterback, and this idea that Maye is multiple tiers above him. Waldman wrote a column explaining why comparing the two is unfair for multiple reasons. It starts with reminding everybody of the damage done to Williams’ development last year.

People don’t factor that into the conversation nearly enough.

When I hear about the commentary regarding Caleb Williams, I suspect too many people are watching Red Zone.

He’s bad, and Ben Johnson knows it. His performances are uneven. He’s not consistent enough.

Wrong. Wrong. And, yes, wrong.

Folks are looking at his 61 percent completion percentage, 7.3 yards per attempt, and his 9 passing touchdowns as solid but not in the same tier as fellow rookies Drake Maye or Bo Nix this year. These comparisons are as consequential as basing player analysis on Red Zone.

Nix is in Year 2 of their offenses with legitimate offensive architects on staff. Maye’s experience working under center was in an offense that had better fundamental structures in place that you’d expect from an NFL scheme…

…The Bears offensive architect last year was the equivalent of a waiter posing as an architect. Comparing Maye’s bad scheming to Williams’ situation is like comparing a grape to a kumquat…

…Caleb Williams is not remotely bad. If anything, he’s a dynasty value if the Red Zone watchers are buying the narrative. Williams is a starter in many re-draft leagues as QB13 on Sunday and for the season thus far — and doing it in a new offense.

We forget he endured a disaster in 2024 — a disaster that none of his rookie peers would have handled any better, much less survived it.

Caleb Williams had zero stability last year.

People can talk about Maye being in a bad situation, too, but that was less about the offensive system and more about the lack of talent around him. Former Patriots offensive coordinator Alex Van Pelt at least understood how to build a scheme around a young quarterback. He’d done that to some success in Tampa Bay with Josh Freeman. He also helped Kevin Stefanski do that with Baker Mayfield in Cleveland. Maye had the same head coach and offensive coordinator all season. Caleb Williams had two of the former and three of the latter.

While Maye did change systems this offseason, it didn’t really reset his development. That wasn’t the case for Williams. Head coach Ben Johnson had to start everything over due to the damage done the previous year. It meant Williams would have to endure some growing pains before he got on track. We’ve seen that unfold over the first half of this season. Waldman believes there have been more than enough signs that things are going in the right direction. Some patience is required.

Why Trent Grisham Makes Sense for the White Sox This Offseason

Oct 1, 2025; Bronx, New York, USA; New York Yankees center fielder Trent Grisham (12) celebrates his double against the Boston Red Sox during the seventh inning of game two of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images

When The Athletic released its top 50 free agents for the 2025–26 offseason, the White Sox were linked as potential fits for five of them. While a few names—such as Gleyber Torres and Jorge Polanco—felt like odd fits, one player on the list stands out as an ideal addition for the 2026 roster.

The team’s most pressing needs remain at the corner infield spots, in the bullpen, and possibly in the outfield, depending on whether the club decides to retain Luis Robert Jr. and Mike Tauchman.

Outfielder Trent Grisham is the first player on Jim Bowden’s list who makes genuine sense for Chicago. The 29-year-old is coming off a breakout season with the Yankees, hitting a career-high 34 home runs and posting a personal-best 3.5 WAR. 

His left-handed power would play perfectly at Guaranteed Rate Field, and he could serve as a right-field upgrade over Tauchman in a platoon role until top prospect Braden Montgomery is ready for the majors. 

A two-time Gold Glove winner in center field, Grisham has also seen limited action in the corner outfield positions, logging fewer than 20 games each in left and right. While he doesn’t hit for average, his disciplined approach at the plate aligns with the organization’s growing focus on patience and on-base ability. He owns a career 12% walk rate and drew 82 walks last season.

Grisham also brings with him postseason experience, appearing in 26 playoff games during his time with the Brewers, Padres, and Yankees. 

Even if the White Sox retain both Robert Jr. and Tauchman, they’ll still feel the loss of veteran leader Michael A. Taylor, who retired at the end of the season. Taylor appeared in 134 games for the White Sox, the third most of any player on the team. If the White Sox were to pick up Robert Jr’s option and flip him at the deadline, Grisham could shift into center field. 

Bowden projects Grisham to command a two-year, $30 million deal—well within the team’s financial reach.