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2026-27 Offseason Plan Project

MikeyB’s Offseason Plan

By MikeyB

10:48 AM CDT on October 24, 2026

PREAMBLE

It's been a while since I've formally done one of these (I distinctly recall arguing with KenWO about my plan to replace Alexei Ramirez with Brad Miller). Let's see what we can make happen here.

ARBITRATION-ELIGIBLE PLAYERS

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

Vargas is obvious. Sox seem to think they've got Doyle ready to hit in 27. Trading Brazoban away later.

OTHER IMPENDING FREE AGENTS

  • None

Would love to keep Newcomb as a reliever, but I think he's going to sign as a SP. Grichuk was fun, but I wonder if he tries to find a job as a full-timer this offseason.

FREE AGENTS

Offering lots of opt outs. Sox have the ability to take some risk with low payrolls, a young roster, and a few key guys coming up in the next few years in the minors.

No. 1 SP Tarik Skubal (5 years, $225 million, Player Opt Out after years 3 and 4) - This deal would start at $35 million in 2027 and increase by $5 million per year after that. It's essentially a 3 year deal for $120 million, with 2 option years for Skubal at $50 and $55 million at the end. He could average $40 million per year and re-enter free agency at age 32. Tons of risk for the Sox on the back end for sure if there's a significant injury.

No. 2 C Austin Hedges (2 years, $10 million, Player Opt Out after year 1) - $5 million in 2027 for a backup catcher. Could be a nice compliment to Teel, playing a lot vs. lefties. Honestly I have no idea what kind of offers he's going to get though after his 2026 season.

No. 3 IF Edmundo Sosa (2 years, $10 million, Player Opt Out after year 1) - $5 million in 2027 for a Utility Infielder who hits righties well.

No. 4 OF Lane Thomas (1 year, $3 million) - Can fill the Randall Grichuk role for less than I'm imagining Grichuk might get offered this year. If you can get Grichuk back for $3 million and a platoon role though, I'm happy with that too.

TRADES

After trading to take on payroll last year, we're going back to attempting to shed payroll by giving away some prospects.

No. 1: Trade Luis Castillo and Edgar Quero to the A's for Luis Severino. This is nearly a 1 for 1 swap on salary. Severino was good but not healthy, and the Sox need a pitcher who could be usable in the playoffs. Castillo was bad but healthy, and the A's could use an inning eater, plus they get a prospect who had some real shine as recent as 2024 in Quero, who maybe just needs a change of scenery. I'm hoping for a healthy year from Severino here, slotting him in as the Sox #3 starter after Skubal and Burke.

No. 2: Trade Andrew Benintendi, Huascar Brazoban, Shane Smith, and $5.1 million to the Nationals for a bag of balls. The Nationals essentially eat $10 million of salary for the Sox here, and in exchange they get Brazoban for their bullpen, Smith as a potential reclamation project, and Benintendi honestly provided more value at DH than they got for most of 2026. Clearing $10 million of payroll allows me to finagle some Skubal money from Jerry.

No. 3: Trade Luisangel Acuña and Ky Bush (or some similarly rated prospect) to the Angels for Robert Stephenson. This gives the Angels a couple of young guys to hope on, and the Sox get a right-handed reliever who I like a lot more than Brazoban for only $1 million more than Brazoban. It's possible I'm overestimating the value of Ky Bush here, but would be quite willing to swap in a number of prospects here.

SUMMARY

I believe this comes in at roughly a $141,000,000 40-man roster including salary deferrals and trades. I'm calling up Jaden Woods from the minors for the Opening Day Roster and adding Brooks Baldwin back from the IL to the 26 man as well. Hopefully Vasil is back midseason and ready to fill the Sean Newcomb role.

While some people are worried about the Swing and Miss in the offense, I'm not. They scored a boatload of runs this year and should have beaten the Guardians in the playoffs if there was any starting pitching available.

Starting Position Players (no changes from 2026):

1B Munetaka Murakami
2B Chase Meidroth
SS Colson Montgomery
3B Miguel Vargas
C Kyle Teel
LF Sam Antonnaci
CF Tristan Peters
RF Braden Montgomery

Bench:

C Austin Hedges (starts most games vs. LHP, Teel to the bench)
OF Lane Thomas (starts in RF most games vs. LHP, Braden to the bench)
OF Brenton Doyle (starts in CF most games vs. LHP, Peters to the bench or LF)
Utility Brooks Baldwin (we'll see how the elbow holds up, but I would be good playing him a bunch vs. RHP at pretty much anywhere other than CF, 1B, and C)
IF Edmundo Sosa (gives off days to Vargas (or Vargas plays 1B) and Colson, pinch hits against righties, plays in pretty much every game in some fashion)

The Pitching Rotation has much more upside in 2027 than 2026, although I'm certainly taking a risk on Severino being healthy for 2027. The bullpen is potentially a step down from 2026, because Newcomb will be nearly impossible to replace. Hopefully Anthony Kay can fill that role to some extent until Vasil comes back. Four righties in the rotation could lead to lots of Opener usage again from Venable, which I'm fine with.

SP1 LHP Tarik Skubal
SP2 RHP Sean Burke
SP3 RHP Luis Severino
SP4 RHP David Sandlin
SP5 RHP Davis Martin (McDougal, Thorpe, Kay, or Cannon could all slot in here as needed for injury purposes or if Martin can't get back to his 2026 1st half form)

RP LHP Jaden Woods (or Berroa, Murray, Schweitzer, etc. based on the Spring)
RP LHP Anthony Kay (long man) RP LHP Bryan Hudson RP RHP Jordan Hicks
RP LHP Noah Schultz
RP RHP Robert Stephenson
RP LHP Hagen Smith
Closer RHP Grant Taylor (Really struggled with this decision. On one hand, I think he could be an ace. On the other hand, a number of relievers sat near the top of the leaderboard in WPA in 2026, and I think Taylor could get there in 2027, especially if Will gives him more 2 inning outings)

I think this is easily the best team in the division, at just $141,000,000 for the 40 man roster, but still 1 corner bat and 1 SP away from being the best team in the AL. I feel decent about the bench if any 1 or 2 position players go down for any extended time, especially if Bonemer is ready to hit at the MLB level by the Summer. Certainly nervous about the rotation, although hopefully McDougal and Thorpe look strong to start the year and could come up if Severino gets hurt again.