PREAMBLE
The White Sox have reached the point where the goal should be competing, not rebuilding. I want to build on that progress without sacrificing (most of) the young core that got us here.
My approach is to prioritize starting pitching, improve the bullpen and defense, and give our young position players room to develop. I’m willing to spend on the right players, but I don't want to commit significant money or prospect capital just to make headlines. With a $130 million payroll target, the challenge is to improve the roster while maintaining flexibility for the trade deadline and beyond.
The goal is to win the AL Central in 2027 and build a team capable of making a deeper postseason run, without compromising the organization's future.
ARBITRATION-ELIGIBLE PLAYERS
- Miguel Vargas: Tender
- Brenton Doyle: Tender
- Joey Bart: Non-tender
- Huascar Brazobán: Tender
- Jordan Leasure: Non-tender
- Chris Murphy: Non-tender
I would be open to bringing all of the non-tender guys back in some capacity. I'm betting Bart will receive that type of money elsewhere, though.
OTHER IMPENDING FREE AGENTS
- Erick Fedde
- Sean Newcomb
Erick Fedde - 1 year, $2.5 million
Having someone who only performs well with the White Sox is a gift, and we all need to accept it. Bring Fedde back on a one-year deal and let him keep doing whatever Sox-specific magic he's doing.
Sean Newcomb - 3 years, $24 million
Sean will no doubt receive multiple-year offers after the season he had. I think it'll take a third year to seal the deal, and I'm willing to make that commitment to keep a valuable lefty in the bullpen.
FREE AGENTS
Jake Bauers - 3 years, $45 million
We have to free up first base from the likely world champion Brewers for Andrew Vaughn. I like Bauers because of his positional flexibility. If the Sox want to move Murakami to DH more often, Bauers or Vargas could handle first base. Depending on where Caleb Bonemer eventually slots in. For now, I’d plan to start Bauers in left field most of the time. He’s a decent corner outfielder who would slot in quite nicely in the middle of the order. From nearly retiring from baseball a few years ago, to a big payday.
Tyler Mahle - 2 years, $30 million
Mahle’s season was a bit uneven after splitting time between San Francisco and Atlanta, but he finished the year well and brings some stability to the middle of the rotation. A two-year deal gives the Sox an experienced starter without making a long-term commitment.
Pete Fairbanks - 1 year, $5 million
Revisiting an old target from last year, when the Sox were rumored to be chasing him, it seems like they dodged a bullet. Fairbanks was terrible for Miami this past year, but the bullpen could still use another high-leverage arm. He has the potential to bounce back, and at this price, I’m willing to take the chance. If he can return to his pre-2026 form, he gives the Sox someone with legitimate closing experience and allows Venable to use Taylor as he sees fit.
TRADES
No. 1: Trade Davis Martin to the Tampa Bay Rays for Shane McClanahan.
Trading with Tampa is always a risk. They could tap into Davis Martin's first month of the season and get him to pitch that way consistently for years. McClanahan, meanwhile, has undergone two Tommy John surgeries, so there's plenty of risk on the other side of this deal, too.
But for a White Sox team that isn't going to be able to land a true top-of-the-rotation starter in free agency at this stage, I'm willing to gamble on McClanahan. At $6.6 million for one season, the potential upside is too enticing to ignore. If he's healthy and returns to anything close to his previous form, the Sox could have a legitimate frontline starter at a fraction of what that caliber of pitcher would cost on the open market. If it doesn't work out, they've lost a reliable starter in Martin, but haven't committed significant money or years to the gamble.
It's a risk, no doubt, but one I think this team needs to take if it wants to compete without blowing up the budget.
No. 2: Trade Colson Montgomery to the St. Louis Cardinals for Masyn Winn
Yeah, I know. Nobody is going to like this one.
I'm admittedly selling low on Colson, and I'm fully aware of the potential to regret this trade if his power translates into consistent major league production. A shortstop with 30-homer potential doesn't grow on trees, especially one who is still young enough to figure things out.
But Masyn Winn is one of the best defensive shortstops in baseball, and I think his glove would make a real difference for this team. He's not much of a force at the plate right now, but the defensive floor is awfully attractive, and there's still room for him to become a more consistent hitter. I want a team that can prevent runs as well as score them, and Winn gives the Sox an elite defender at one of the most important positions on the field.
From St. Louis' perspective, the fit makes sense, too. JJ Wetherholt gives the Cardinals another potential shortstop option, while Montgomery offers the kind of power upside their lineup needs. If Colson can turn that raw power into consistent production, St. Louis could end up with the more valuable bat.
I'm also thinking about Roch Cholowsky here. I want to give him time to develop rather than force him onto a major league roster before he's ready. Winn gives us a legitimate long-term answer at shortstop in the meantime, and we can figure out the rest when Cholowsky gets here. Nothing is guaranteed with prospects, and if Roch develops quickly enough to force the issue, that's a good problem to have. We'll deal with it when the time comes.
This is a tough trade to make because I'm giving up the possibility of a middle-of-the-order power hitter for a player whose value is driven heavily by defense. But I'm betting on Winn's glove, his age, and the value of having a reliable shortstop while allowing Cholowsky to develop on his own timeline. Sometimes you have to trade a little upside to make the overall roster better, and I'm willing to take the heat for this one.
SUMMARY
Last Roster Move: DFA Andrew Benintendi
I'd probably wait until spring training to make this move. Give Benintendi a chance to come out flying and show that he still has something to offer, but I think it's time to cut bait and give a younger player the bench spot he'd otherwise be taking up.
I am under the assumption the league minimum salary is $1 million.
Summary and Roster
This plan puts the White Sox at approximately $129.45 million in listed player salaries, plus the $1.5 million deferred to Liam Hendricks and the $14.5 million you are eating on Andrew Benintendi, so I will have to go upstairs to the boss man and convince him that $145.45 million total is the best course of action. I like the flexibility of the roster we've built.
There are plenty of opportunities for young pitchers to make the jump. If Castillo continues pitching the way he did last year, there's a spot to be claimed. If McClanahan can't stay healthy, there's a spot. If Kay struggles, he could be moved to the bullpen or replaced. And there will always be opportunities in the bullpen throughout a season.
The position-player group offers similar flexibility. There's room for Bonemer to force the issue early if he hits his way to Chicago. The combination of Bauers, Vargas, and Murakami gives us options at first base, third base, left field, and DH, while Winn provides a defensive anchor at shortstop.
The goal is to enter 2027 with a roster capable of competing for the AL Central while keeping the door open for younger players to earn their way onto the team. I don't want to block a prospect who's ready, and I don't want to keep running out a veteran simply because he's already on the roster. If the young guys perform, there will be opportunities for them to take jobs.
C - Teel ($1)
1B - Murakami ($17)
2B - Meidroth ($1)
3B - Vargas ($5.4)
SS - Winn ($2)
LF - Bauers ($15)
CF - Peters ($1)
RF - Montgomery ($1)
Backup Catcher: Quero/Romo/Turner/etc. ($1)
Utility Players (2): Baldwin, Bergolla, Acuna, etc. ($2 total)
Outfielder: Doyle ($3.6)
SP - Burke ($1)
SP - McClanahan ($6.6)
SP - Mahle ($15)
SP - Kay ($5)
SP - Castillo ($22.75)
RP - Hudson ($1)
RP - H. Smith ($1)
RP - Newcomb ($8)
RP - Fedde ($2.5)
RP - Brazoban ($1.6)
RP - Hicks ($8)
RP - Fairbanks ($5)
RP - Taylor ($1)
