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2026-27 Offseason Plan Project

Hug Prospects, Not Money

By Dan (@_FarceMajeure)

9:01 AM CDT on October 30, 2026

PREAMBLE

The AL Central is weak and aggressive moves on FA can solidify the team's contender status with minimal trades. It might make for an expensive 2027 but it will put the team in a very good place for the years that follow.

ARBITRATION-ELIGIBLE PLAYERS

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

Vargas is a no-brainer. Doyle is insurance against Peters regressing and should be hitting better after the off-season. Brazoban and Leasure are cheap relative to their upside and both can still be traded if better options come around, Leasure also doesn't take a 26-man spot while recovering from TJ.

OTHER IMPENDING FREE AGENTS

  • None

Had a very hard time letting go of the following three:

Maybe Newcomb had enough fun to stick around for another year but I wouldn't count on it if another team will pay him more and let him start.

Richards is a great option for eating bad innings but why not have an even better reliever for the job you can also use in important non-mop-up spots.

Hate to let Grichuk walk but he probably wants money/years the sox are better spending elsewhere.

Honorable Mention to Fedde but we need to do better.

All others can pack their knives and go.

FREE AGENTS

Shortstop (Colson should probably start 2026 in the minors if not traded) 2027 Budget Impact: $4.5M to 18M
No. 1A: Taylor Walls (1 year, $4.5 million) Assumes Tampa Declines club option.
No. 1B: Isiah Kiner-Falefa (1 year, $8 million) If Walls stays with Tampa.
No. 1C: JP Crawford (2 years, $36 million) Almost definitely too expensive to sign but worth it in a world where Colson is traded and we have to patiently wait for Carlson and/or Cholowsky call-ups, year 2 is a mutual option.

Outfield - 2027 Budget Impact: $32.5M
No. 2: Randy Arozarena (5 years, $125 million) An opt-out and a player option in there somewhere. He plays LF and can move to DH after Benintendi goes or 1B if Murakami doesn't stick around.
No. 3: Tyrone Taylor (2 years, $15 million) Mutual option for the second year. Insurance on all OF positions and a solid option if Sox are priced out or ruled out of the Arozarena convo.

Starter - 2027 Budget Impact: $12M to 20M
No. 4A: Shane Beiber (3 years, $36 million) Opt out after year two.
No. 4B: Casey Mize (1 year, $20 million) Prove it contract.

LHP Reliever - 2027 Budget Impact $3.6M to 7.2M
No. 5A: AJ Minter (1 year, 7.2 million) Need good lefties, especially if Newcomb doesn't re-sign
No. 5B: Strahm (1 year, 3.6 million) Ditto.

RHP Reliever - 2027 Budget Impact $5M to 11M
No. 6A: Bryan Abreu (2 years, 22 million) Need leverage arms if Taylor's going to start.
No. 6B: Pete Fairbanks (1 year, 8 million) Ditto.
No. 6C: Kenly Jansen (1 year, 5 million) If priced out of Abreau or Fairbanks

Total Free Agent 2027 Budget Impact: $45.6 Million to $88.7 Million

TRADES

No. 1: Trade Benintendi, retaining a portion of his salary, with prospects Mogollon and Wolkow. Any team that will take him, keep no more than 7.5 on the books.

SUMMARY

This assumes Bonamer, Carlson, and Cholowsky are not ready for the Show until the trade deadline or 2028, and that the sox shouldn't move their prospect depth aside from the couple it would take to off-load Benintendi on another team (I suggest Wolkow and Mogollon to the Giants)

How do you solve a problem like Colson Montgomery? I wanted to minimize trades but if he could be flipped for a reliever or two that'd be ideal. Assume he isn't traded and starts at AAA then Walls is the ideal replacement, Crawford is the expensive alternative, and Kiner-Falefah is the likely middle ground unless some team finally offers him a long term deal. If they give the spot to Murray, trade Acuna for a pitching prospect.

Castillo is also a problem but I don't think any team is going to step up to help us fix it. At best he fits into the rotation, at worst he sits in the bullpen and handles mop-up. Either way, turn his salary into innings we don't want anyone else pitching. Better him than Seranthony.

I think Shultz, Sandlin, Thorpe, and McDougal are all still very promising but they should be starting in Charlotte, not relieving in Chicago. Call them up when ready and if needed but shop for alternatives elsewhere and consider trading them for proven Major League SP and/or RP at the deadline.

26-Man Roster
C Kyle Teel
C Edgar Quero
1B Murakami
2B Meidroth
2B/DH Antonacci (He liked DHing)
SS Walls or Kiner-Falefah while Colson resets, Crawford if Colson is traded.
SS Acuna or Murray
3B Miguel Vargas
LF Randy Arozarena
CF Tristan Peters
CF Brenton Doyle
RF B. Montgomery
RF Tyrone Taylor

SP1 Sean Burke
SP2 Casey Mize or Shane Bieber
SP3 Davis Martin
SP4 Anthony Kay
SP5 Luis Castillo

RP Mike Vasil - Right Handed Long Relief
RP Hagen Smith - Left Handed Long Relief or Setup
RP Huascar Brazoban - Right Handed Middle Relief
RP Jordan Hicks - Right Handed Middle Relief & Setup
RP Bryan Hudson - Left Handed Middle Relief & Setup
RP Strahm or Minter - Left Handed Middle Relief & Setup
RP Abreu, Fairbanks, Jansen - Right Handed Setup or Closer
RP Grant Taylor - Right Handed Long Relief, Setup, Stopper, Closer, or turn him into a Starter if he's ready and no one else seems to be.

Costs:
Arbitration - $11.6 Million
Free Agents - $45.6 Million to $88.7 Million
Trade - $7.5 Million back from Benintendi
Total - $49.7 Million $92.8 Million