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2026-27 Offseason Plan Project

Under the Circumstances’ Offseason Plan

By Under the Circumstances

1:32 PM CDT on October 31, 2026

PREAMBLE

The White Sox shocked everyone this year by being competitive and winning a playoff series as one of the youngest teams in baseball. In a normal offseason, we'd be talking about major investments, but this year will be anything but normal. What will baseball look like on the other side of the impending lockout?

As GM, I want to fill the clear and obvious holes on this roster, while still allowing for young guys to improve and not blocking our prospects. I'd rather sign FAs than trade prospects unless it's at the bottom or top of the roster.

ARBITRATION-ELIGIBLE PLAYERS

  • Miguel Vargas: Tender
  • Brenton Doyle: Tender
  • Joey Bart: Non-tender
  • Huascar Brazobán: Tender
  • Jordan Leasure: Non-tender
  • Chris Murphy: Non-tender

Doyle is perfectly fine as a 4th outfielder. Good defense, hope he figures out the bat. Brazoban is cheap, and I'll have no issue DFA-ing him if his struggles continue.

Bart seems like he was declining before the injury, and I need a better backup. Leasure and Murphy - bye.

OTHER IMPENDING FREE AGENTS

  • None

Would love to have Fedde and Newcomb back, but I'm aiming higher for my starters. I'm happy with what Grichuk gave us this past year, but there is no way I'd expect him to repeat that.

FREE AGENTS

Brandon Woodruff (3 years, $60 million). Top of the rotation stuff (when healthy), and pairs nicely with Burke. I think the third year will be necessary to get him to sign before the lockout, which is my goal.

Ian Happ (3 years, $54 million). Gives us a true LF that is above average defensively. Has crushed righties over his career and only 31. Again, give that third year to get him to sign early.

Ramon Laureano (1 year, $2 million). Now we play the waiting game. Assuming teams don't rush to sign him after a down season, we pick Laureano up before next season starts for a pittance. If he can get back to his level of play from the two prior years, that would be huge.

TRADES

Javier Mogollon to the Mets for Luis Torrens and $3 million. We need a backup catcher that can credibly play whenever needed, and step in if the injury bug strikes Teel again. Torrens is one of the best defensive backstops in the league, has a little pop, and hits above the Mendoza line. The Mets gave him an extension mid-season, but after a failed year they decide to cut some salary, and a 30yo backup catcher making almost $6 million isn't what they have in mind.

Andrew Benintendi, Ely Brown, and $6 million to the Rockies for Ryan Ritter. I have two problems with the roster - Benintendi is making too much for not enough production, and I have no credible utility infielder unless Baldwin or Murray come back early and fully healthy (yeah right). So we send Benintendi with some cash and a productive hitting prospect to a team that needs all the hitting help they can get. Ritter comes back to provide the utility coverage. Good fielder, hit well in the minors, but had a dreadful first two seasons in the bigs. He's also a local kid, and you know we'll take any of them we can get.

SUMMARY

Catcher Kyle Teel $800,000
1B Munetaka Murakami $17,500,000
2B Chase Meidroth $800,000
SS Colson Montgomery $800,000
3B Miguel Vargas $5,400,000
LF Ian Happ $18,000,000
CF Tristan Peters $800,000
RF Braden Montgomery $800,000
DH Sam Antonacci $800,000

Backup C Luis Torrens $5,750,000
Util IF Ryan Ritter $800,000
4th OF Brenton Doyle $3,600,000
Util Ramon Laureano $2,000,000

Hitter total = $57,850,000

Gotta keep Antonacci's bat in the lineup as much as possible, but I don't want to weaken every other infield position to do it.

SP1 Brandon Woodruff $20,000,000
SP2 Sean Burke $800,000
SP3 Hagen Smith $800,000
SP4 Davis Martin $850,000
SP5 Anthony Kay $5,000,000
CL Grant Taylor $800,000
SU Jordan Hicks $12,500,000
RP Huascar Brazoban $1,600,000
RP Bryan Hudson $800,000
RP Jaden Woods $800,000
RP Jairo Iriarte $800,000
LR Luis Castillo $24,150,000
LR Noah Schultz $800,000

Pitcher total = $69,700,000

Hagen deserves a legit shot at starting, and while I think Taylor does as well, he's been in the bullpen for two years now, and I don't want to stretch him out. Woods and Iriarte pitched great in AAA and I'll peg them in for bullpen spots. Not sure how long it'll take Vasil to get back to playing strength, but Castillo can keep his spot warm for now.

With the Hendriks deferment and cash going both ways (I'm including half of the $8 million from Boston for Hicks and half the $3 million for Torrens), that's another $2 million, putting our total at $129,550,000. Let's go get a World Series victory of our own!