ChiSoxFanMike’s White Sox Offseason Plan

What a season it was for the White Sox. After three straight years of 100+ losses, the team took a massive leap forward in 2026, improving by 24 wins from their 102 loss campaign a season earlier. One of the true feel-good stories of MLB, the season ultimately culminated in a playoff berth for the first time since 2021 and a playoff series win for the first time since 2005.

It has been a long time coming, but we can now wholeheartedly say that the organization is trending in the right direction again and that there is hope for the future. Both the coaching staff and core of the team will largely return next season, an indication that things are on the right track. With a young roster, more top prospects coming, and no guaranteed contracts on the books after the 2027 season, the sky is the limit for what this franchise can be in the future.

​With that comes big responsibility and a new set of challenges for the front office. This is no longer a rebuilding situation and the offseason moves should reflect that. The expectation is that the team will not only make the playoffs again, but overtake the Guardians in the division following a disappointing ALDS in which they could not seal the deal after taking a 2-0 series lead. Chris Getz will be operating from a position he has never been in as the White Sox General Manager until now: constructing a team hopeful of winning the World Series next year. This plan will explain what I would do if I were in his shoes.

Payroll Estimate

Like any other offseason plan, the payroll is an integral aspect of constructing the roster. The team’s 2026 payroll was just over $100 million in 2026, ranking just 24th in MLB per Spotrac. There is no doubt in my mind that payroll will increase in 2027 given the team’s success last season, but multiple factors make it difficult to estimate the exact number they will have to work with.

One of those factors is Jerry Reinsdorf, and by extension, Justin Ishbia. The team cut payroll dramatically over the last several seasons as they went into a rebuild, but there is precedent for Reinsdorf to spend at a reasonable level when he feels the team is ready to contend. The 2022 team, for example, had a payroll north of $200 million with a roster full of established veterans. Ishbia’s involvement is also an interesting wrinkle. It’s anyone’s best guess as to how involved he will be this offseason knowing that this will eventually be his franchise.

The impending lockout is another major consideration. The collective bargaining agreement is set to expire on December 1st, and there have already been discussions of a potential salary floor and cap among other changes. While I am not going to speculate on how that situation ultimately plays out, it’s possible we could see a league-wide frenzy of action before that happens so teams have some level of certainty heading into what could be a considerable period of time with no activity.

With these factors in mind, I will give myself $175 million to work with to build the 2027 team. It is entirely possible that they still won’t spend at this level, but it’s within reason given how the franchise has operated historically, and this figure would have ranked just 16th in MLB last season. It’s a number I feel is at least somewhat realistic and not a fantasy scenario with zero chance of happening in real life. I will use Dealin’ The Cards model as a guideline for projected player salaries and the overall team payroll. While there might be slight discrepancies for arbitration and league minimum salaries, the overall numbers should be fairly close.

Arbitration Eligible Players

One of the first orders of business is evaluating the team’s arbitration eligible players and whether to tender them contracts for next season. I examined the group of players that fall into this category not too long ago, with explanations for each decision.

In that article, I went with non-tendering Joey Bart. For the purposes of this plan, however, I will tender him a contract. The catching market in free agency doesn’t do much for me and I think he will be serviceable enough as a relatively productive backup for Kyle Teel at a minimal price point. All my other decisions remain the same.

Tender: Miguel Vargas, Joey Bart, Brenton Doyle, Huascar Brazobán

Non-tender: Chris Murphy, Jordan Leasure

The Andrew Benintendi Conundrum

It’s a very low bar, but I felt 2026 was Benintendi’s best overall season in a White Sox uniform. While his numbers still weren’t great, he provided several clutch moments while serving as a veteran leader in the clubhouse. To be completely honest though, I do not want him on this team next year. He only played a whopping 58 innings in the field all season, and as a roughly average offensive platoon DH, I think it’s a waste of a roster spot to keep him on the team. He just doesn’t hit well enough as a DH to justify keeping him around given that he doesn’t provide value anywhere else on the field. Removing him from the roster would create significantly more flexibility, both financially and in terms of roster fit.

Now entering the final season of the five-year/$75 million contract he signed in January 2023, enough time has passed that the contract is no longer a completely untradable albatross. He is owed $15.1 million for the 2027 season, and while he certainly doesn’t have any positive trade value at that price, I do think it is possible to unload him in a salary-dump scenario with a bad team that can absorb him for a season. And that is what I will do.

Trade #1

DH Andrew Benintendi, RHP Shane Smith, and $5 million to the Washington Nationals for RHP Joe Glassey

The Nationals are a team I identified as a potential fit for a salary-dump trade. I view them similarly to how I viewed the White Sox at this time last year. That is, a team on the rise that is not quite ready to be a legit contender, but is on the right track. They lost quite a bit of offense by trading Luis Garcia Jr. and Curtis Mead at last year’s trade deadline, and there is a place for Benintendi to get DH at-bats and serve as a veteran presence on that team.

In exchange for taking Benintendi off the White Sox hands, I will send $5 million and Shane Smith to the Nationals in this deal as a sweetener. Smith fell on hard times last season, but showed flashes of being a quality pitcher in 2025 and is still just 26 years old. He represents an intriguing reclamation project for Washington as they look to improve a pitching staff that ranked among the worst in MLB in 2026.

In exchange, I have Joe Glassey heading back to the White Sox. A 25-year-old right-handed reliever who is a local product, he put up a 1.64 ERA in 40 appearances with 76 strikeouts in 49.1 innings across three different minor league levels in 2026 and could potentially earn a role in the big league bullpen down the line. He is probably just a guy who won’t ever make a considerable impact at the MLB level, but that is the type of player you expect in return for a Benintendi salary dump.

In a lot of ways, this deal is reminiscent of the Jordan Hicks and David Sandlin trade with the Red Sox last offseason, except the White Sox are on the other end of the deal. They free up approximately $10 million and a roster spot in this trade while only giving up a guy who likely isn’t going to be in the 2027 plans anyway. I am willing to part with Smith in a trade like this to create more flexibility for the other moves that will be part of this plan. From the Nationals’ perspective, I think they would take Benintendi on for one season if they receive an MLB-ready arm like Smith who could factor into what they are trying to build.

Trade #2

LHP Anthony Kay to the San Francisco Giants for OF Damian Bravo

Signed to a two-year/$12 million contract last offseason after a stint in Japan, Kay is another guy who I felt did a serviceable enough job for the 2026 White Sox. While his numbers weren’t anything all that special, he took the ball whenever he was asked and generally did enough to give the team a chance to win.​

This particular trade is not as straightforward for me as the Benintendi one because there is no doubt in my mind that Kay is better than Luis Castillo at this point in their careers, and I think there is a scenario in which Kay could contribute positively to the team next year. But with Castillo being paid nearly 5x as much next season, Kay is the odd man out. Of the two, it is significantly easier to trade Kay because he is only making $5 million in 2027. I do not want both of them in the rotation next year, and Kay’s tendency to lose command and to hit batters gives me reservations about putting him in a full-time relief role. As such, he will be playing elsewhere next year.

Bravo was the Giants’ 15th-round pick in 2025 and has put up good numbers in the minors while being roughly the average age of the leagues he’s played in. An outfielder, he is another lottery-ticket prospect who represents some return for Kay and will be worth monitoring in the farm system.

The Giants are another team I don’t expect to be very good next year but need pitchers to fill a rotation and eat innings. I also think there is a possibility that pitching in pitcher-friendly Oracle Park would benefit Kay and potentially give the Giants an opportunity to flip him at the deadline. From the Giants’ perspective, the hope would be that Kay pitches well enough to be traded for a prospect better than Bravo.

This trade frees up another $5 million and an additional roster spot, which was my intention from the beginning. Between this trade and the Benintendi trade, an extra $15 million has been shaved off the payroll before a single addition is made.

Trade #3

LHP Noah Schultz, SS Billy Carlson, OF George Wolkow, RHP Tanner McDougal, and C Fernando Graterol to the Los Angeles Angels for LHP Reid Detmers and LHP Samy Natera Jr

This is where things get fun. Reid Detmers is a name that has come up frequently in White Sox circles in recent months and is someone that I have had my eye on for a while now. Taken one pick ahead of Garrett Crochet in 2020, Detmers bounced between the starting rotation and bullpen between 2021 and 2025, achieving success in both roles but also struggling at times to find consistency.

2026 was his true breakout season. In 185 innings across 32 starts, he recorded a 3.36 ERA, 3.01 FIP, 1.04 WHIP, and 211 strikeouts with only 48 walks. The metrics also back up his performance. He grades out favorably in most categories, in large part because of his devastating slider, which opponents hit just .187 against last season. It appears that the light has finally turned on for him, and in my opinion, he is one of the more underrated pitchers in the league. I feel he would have significantly more fanfare and attention if he played for a better team.

Detmers’ contract status is another key reason why he appeals to me. He will not reach free agency until after the 2028 season, so he has two years of affordable team control remaining. For a team like the White Sox that historically does not spend money on elite pitching in free agency, those two seasons of cost certainty are key. Bringing Detmers aboard would provide a much-needed boost to the rotation for the next two seasons, and with Justin Ishbia likely playing a bigger role down the line, perhaps they could keep him beyond 2028 as well.

Samy Natera Jr.’s inclusion in this trade is not coincidental. He is another guy who caught my eye this past season. Soon to be 27, he just concluded his rookie season and posted impressive numbers. In 31.2 innings across 28 relief appearances, he struck out 48 while recording a 3.13 ERA. He is unique in that he threw his four-seam fastball 80% of the time, but it was a truly effective pitch and the results proved it.

Natera Jr. is a long-term upside play in this trade. He is not projected to become a free agent until 2033, making him a potential integral part of the bullpen for years to come. Lefty relievers with the ability to miss bats are highly sought after and he is someone I would like to have in this bullpen. It is worth noting that he went on the injured list with left forearm inflammation at the end of last season, but the MRI showed no structural damage. He should be good to go moving forward.

The Logic

The Angels are an organization that have needed to rebuild for a long time. They spent several years in a proverbial no man’s land, and this trade will help get them on the right path again. They already traded Jose Soriano to the Blue Jays at the trade deadline for a few intriguing prospects and this trade will give them an additional package of young players to build with.

Schultz struggled somewhat in his first taste of MLB experience, but has prospect pedigree, high upside, and can immediately slot into the Angels rotation to replace Detmers. Carlson and Wolkow are both very high-upside position player prospects for the Angels to dream on, and McDougal is another interesting arm that is close to MLB-ready. Graterol is a lotto ticket prospect who spent 2026 in the Dominican Summer League but put up good numbers and will be another guy for the Angels to watch progress through their system.

White Sox fans will likely look at this proposal and say they are giving up way too much, but I consider that the price of making a deal. It will not be easy to nab a pitcher like Detmers who will be very desirable on the trade market and has ace-level potential in my opinion. Schultz is the toughest player of this package for me to part with, but I feel like he is someone the Angels would want and it takes two sides to make a trade. From the Angels’ perspective, they cash in on Detmers at arguably his peak value for a substantial package of prospects, while the White Sox add two talented pitchers to help them win right now. I consider this trade a win/win.

Free Agent Signing #1

RHP Michael King to a four-year/$120 million contract

Even with Detmers in the fold, I still think adding another proven veteran starting pitcher is essential if this team wants to be a true contender. Enter Michael King and the first $100+ million contract in franchise history. The 31-year-old right-hander began his career as a reliever but has transitioned to being a full-time starter over the last three seasons and has taken to the role like a glove. He is coming off another strong season with the Padres in which he made 32 starts, posting a 3.21 ERA, 1.18 WHIP, 7.7 K/9, 4.3 bWAR, and 2.6 fWAR over 185 regular season innings.

King has also proven to rise to the occasion when the lights are bright. He allowed only one run in 14 innings this postseason and has a career 1.86 ERA and 0.76 WHIP in 29 playoff innings. The White Sox need more pitchers with proven postseason experience who don’t fold on the big stage, and he provides just that. King recently turned down his player option with the Padres in search of more money, and a contract of this structure would give him a raise from an AAV perspective and add two additional years for even more earnings.

I debated long and hard between King and Freddy Peralta for this spot. Wear and tear was the ultimate differentiator for me. Even though King is a year older, he has roughly 400 fewer MLB innings on his arm than Peralta and was better in 2026. I think he has more good years ahead of him than Peralta, and of the two, I would bet on King being the better pitcher moving forward.

Free Agent Signing #2

OF Seiya Suzuki to a five-year/$125 million contract

The White Sox have never given a free agent a $100 million contract in franchise history, but I have them handing out two such deals this offseason. Even as a hater of all things Cubs, Suzuki is a player I have always admired and thought highly of. He has been a well above-average hitter every year of his career and has shown no signs of slowing down, and his defense in right field improved significantly as well this past season.

As things currently stand, the White Sox lineup is very left-handed heavy after the departure of Randal Grichuk in free agency. Suzuki adds a much-needed right-handed power bat to the middle of the lineup while providing additional thump to an outfield that didn’t show much power last year.

This was another signing I thought long and hard about, ultimately choosing between Suzuki and Randy Arozarena. Both will have qualifying offers attached, meaning the White Sox would forfeit a draft pick to sign either of them. I ultimately lean toward Suzuki because I feel he is the better overall player and already has a friendship with Munetaka Murakami. While forfeiting a draft pick and giving a five-year contract to a 32-year-old isn’t ideal, it’s a trade-off I am willing to make to land a hitter of Suzuki’s caliber.

Free Agent Signing #3

IF/OF Edmundo Sosa to a two-year/$10 million contract

For as productive as the White Sox infield was in 2026, they lacked depth beyond the starters. Luisangel Acuña spent most of the season in a backup infield role but showed very little with the bat and isn’t someone I have much interest in bringing back.

A veteran of parts of eight MLB seasons, the 30-year-old Sosa has always mashed lefties and 2026 was no exception. In 138 plate appearances against southpaws last season, he slashed .290/.343/.492. He also appeared defensively at third base, shortstop, second base, and left field, making him an ideal bench player. He can play multiple positions in the field and is good enough to start against lefty pitchers. Even though he lacks the speed of Acuña and isn’t particularly good against right-handers, I think he is a substantial upgrade in the same role and will see a fair amount of playing time with the way this team will be constructed.

Free Agent Signing #4

RHP Evan Phillips to a one-year/$5 million contract

Historically, I have been against paying free agent relievers who aren’t established closers and this signing directly contradicts that thought process. I have my reasons for why this makes sense, however.

Phillips has a track record of being a quality reliever, especially in the playoffs. He has never allowed a run in 17 career playoff appearances and has some closer experience on Dodger teams that were really good. I want more pitchers who have proven they can handle the big moments. Like King, Phillips is one of those guys. I wouldn’t want or expect him to be the closer for the 2027 White Sox, but his experience in the role provides a safety net and a backup plan if needed.

The biggest question mark for Phillips is health. He has only made 38 regular season appearances over the last two seasons because of shoulder, elbow, and forearm issues and had Tommy John Surgery in June of 2025. Gambling on him to stay healthy is a risk, but it is a chance I am willing to take on a one-year deal. From Phillips’ perspective, I think a prove-it deal makes sense from his side too. If he proves he can stay healthy and contribute in a bullpen for a team that figures to be pretty good, he can enter free agency again next offseason and get a larger payday.

Free Agent Signing #5

RHP Erick Fedde to a one-year/$3 million contract

I can’t quit Erick Fedde, as I advocated for them to bring him back last offseason too. Sure enough they did and he performed admirably. While his stuff and stats aren’t all that impressive, I think he is a valuable innings eater who can pitch both out of the rotation and the bullpen. He seemed to enjoy being part of this team, and while he might get offers elsewhere, I think he would consider returning if the money is comparable.

I will give him a slight raise based on what he did last year to be a swingman on this team. The plan is to have him pitch in multi-inning stints out of the bullpen, but he also serves as insurance in case of an injury in the starting rotation.  

Projected 2027 White Sox Opening Day 26-Man Roster

​Lineup:

DH: Sam Antonacci (24) (L) ($780,000)

3B: Miguel Vargas (27) (R) ($5,400,000)

1B: Munetaka Murakami (27) (L) ($17,500,000)

RF: Seiya Suzuki (32) (R) ($25,000,000)

C: Kyle Teel (25) (L) ($788,000)

2B: Chase Meidroth (25) (R) ($789,000)

SS: Colson Montgomery (25) (L) ($799,000)

LF: Braden Montgomery (23) (S) ($780,000)

CF: Tristan Peters (27) (L) ($780,000)

Lineup total: $52,616,000

Bench:

IF/OF: Edmundo Sosa (30) (R) ($5,000,000)

IF/OF: Brooks Baldwin (26) (S) ($780,000)

C: Joey Bart (30) (R) ($2,900,000)

OF: Brenton Doyle (28) (R) ($3,600,000)

​Bench total: $12,280,000

Starting Rotation:

SP: Michael King (31) (R) ($30,000,000)

SP: Reid Detmers (27) (L) ($7,500,000)

SP: Sean Burke (27) (R) ($793,000)

SP: Davis Martin (30) (R) ($799,000)

SP: Luis Castillo (34) (R) ($24,150,000)

Starting rotation total: $63,242,000

Bullpen:

RP: Erick Fedde (34) (R) ($3,000,000)

RP: Huascar Brazobán (37) (R) ($1,600,000)

RP: Evan Phillips (32) (R) ($5,000,000)

RP: Samy Natera Jr. (27) (L) ($780,000)

RP: Jordan Hicks (30) (R) ($12,500,000)

RP: Bryan Hudson (29) (L) ($798,000)

RP: Hagen Smith (23) (L) ($780,000)

RP: Grant Taylor (24) (R) ($788,000)

Bullpen total: $25,246,000

Total team payroll: $153,384,000

Players Who Just Missed The Cut

C Edgar Quero, IF/OF Rikuu Nishida, OF Tanner Murray, IF/OF Caleb Bonemer, RHP Tyler Davis, RHP David Sandlin, RHP Drew Thorpe, LHP Tyler Schweitzer, RHP Mike Vasil (Tommy John recovery)

Takeaways

I think the biggest eyesore on this entire team is Luis Castillo still in the starting rotation because that does not compute with being a contender. I am willing to give him another chance based on his track record in hopes that an offseason and a spring training with the White Sox pitching coaches can rejuvenate him, but the leash should be very short. As in 2016 John Danks and 2022 Dallas Keuchel level short. If he makes a handful of starts and is still as bad as he was in 2026, I expect them to bite the bullet and part ways with him quickly even if it means eating a substantial amount of money.

There have been a lot of discussions about moving both Grant Taylor and Hagen Smith into the starting rotation, but I do not want to do that just yet. I think another season of being in the bullpen would benefit both of them. I could see a scenario where the team starts to stretch them out for longer appearances throughout 2027 with the intention of making them starters in 2028, which I am fine with. But for now, the bullpen is a good place for them. They both excelled in that role and will be the two highest-leverage relievers on this team.

Caleb Bonemer not being on this roster will probably raise some eyebrows as well. He is a tremendous talent and will likely play a meaningful role by the end of the season, but I do not want to rush his development. We have seen that play out too many times before and it usually causes more harm than good. He can come up when he is ready, but I am not expecting or banking on him to be on the opening day roster. That said, I wouldn’t be surprised if he breaks camp with the team if he has a strong spring. I will also add William Bergolla Jr. to the 40 man roster to protect him from being selected in the upcoming Rule 5 Draft.

Mike Vasil and Drew Thorpe’s omission from this roster is also noteworthy. Thorpe is ahead of Vasil in the recovery process since he had his Tommy John Surgery nearly a year earlier than Vasil, but I think he will start the season in Triple-A as depth. I don’t expect Vasil to become a factor until the summer given that he only had the procedure done in April, but I think both will play roles on this pitching staff at some point in 2027.

Unlike some other plans I have seen, I chose not to hand out any contract extensions. While I was in favor of extending Munetaka Murakami at times last season, I would like to see how he performs in 2027 and whether he can reduce his strikeouts somewhat before committing big money to him. He will be more expensive to retain his services if he has another strong year, but I would be lying if I said the swing-and-miss didn’t concern me a bit. As for the rest of the team, I don’t feel any urgency to extend anyone. Maybe it’s PTSD from the last core, but I want these guys to keep playing hard in hopes of earning bigger contracts and not reward them with big extensions before they have proven anything.

I also did not bring back any of the impending free agents from last year except for Erick Fedde. As much as I like Sean Newcomb and Randal Grichuk, I think we saw the best versions of them last year and feel they are unlikely to replicate what they did this past season. I thank them for a job well done and they hold a special place in my heart, but I am content with each of them going elsewhere.

Final Thoughts

Going into this offseason, the needs of this team are pretty clear in my eyes. I feel they need two proven starting pitchers, a right-handed power-hitting bat, a couple of relievers, and a bench bat. This plan accomplishes all of those things while still keeping the payroll at a reasonable total. In fact, the payroll of the team above is roughly $20 million less than what I allotted myself to spend, before including dead money. And with Castillo, Hicks, and potentially Murakami coming off the books after the 2027 season, they will shed a lot of salary to reload at this time next year.

Should the offseason play out like this, I feel the White Sox would be by far the best and most complete team in the division and have a very realistic chance of making noise in the playoffs. It is a much deeper and well-rounded squad than what they had last year, with lineup balance from top to bottom, and the postseason disappointment against the Guardians should only make this group hungrier and better for 2027. Following a season of growth and excitement, the organization owes it to the fanbase to put in a good-faith effort to meaningfully improve the team. Let’s see if they hold up their end of the bargain.

​Offseason Plan Summary

Trade DH Andrew Benintendi, RHP Shane Smith, and $5 million to the Washington Nationals for RHP Joe Glassey

Trade LHP Anthony Kay to the San Francisco Giants for OF Damian Bravo

Trade LHP Noah Schultz, SS Billy Carlson, OF George Wolkow, RHP Tanner McDougal, and C Fernando Graterol to the Los Angeles Angels for LHP Reid Detmers and LHP Samy Natera Jr

Sign RHP Michael King to a four-year/$120 million contract

Sign OF Seiya Suzuki to a five-year/$125 million contract

Sign IF/OF Edmundo Sosa to a two-year/$10 million contract

Sign RHP Evan Phillips to a one-year/$5 million contract

Sign RHP Erick Fedde to a one-year/$3 million contract