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2026-27 Offseason Plan Project

Can the opener: knoxfire30’s offseason plan

By knoxfire30

10:44 AM CDT on October 24, 2026

PREAMBLE

The Whitesox arrived a year early and benefitted from a weak showing by the American League in 2026 leading to a wildcard birth... before thoughts of this young core rattling off multiple post season appearances over the next decade fill our fandoms hearts, its important to note the 2nd half meltdowns of some of the hitters and pitchers that should be worrisome. My plan is about establishing a better front end of the rotation, while allowing another year of development to take place with the offense.

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 an absolute no brainer, Doyle hit well enough vs left hand pitching and plays a solid premium defensive position. For 3.6 mil and after moving Mason Adams for him he isnt going anywhere. Brazoban was a little up and down especially after the trade deadline but was dominant the first half of the season and its hard to find that lively of a bullpen arm for 1.6 mil on a one year deal. Bart is a 3rd string catcher in a day and age where almost every team carries 2. Leasure and Murphy are internally replaceable and apart of simply trimming the fat on a roster.

OTHER IMPENDING FREE AGENTS

  • Randal Grichuk

I would make a relatively strong offer to Grichuk, he probably produced his 90% outcome with the sox in 2026 and expecting him to repeat that effort would be a fools errand. But a team that primarily will start 3 left hand hitters in the outfield and a lefty hitter at dh, will have plenty of at bats for Grichuk as a pinch hitter and as a starter any time a lefty is on the mound. 1 year 6 mil with a team option for 8 mil in 2028 with a 1.5 mil buyout. I wanted to bring Newcomb back but he has been ridden hard and put away wet many times and the dollar value on a limited budget just wasn't adding up for a team that has other holes to fill and plenty of younger arms trending towards the bullpen. Like with Grichuk I think the Sox got everything and more they could have expected from Fedde and gambling on a repeat performance on a tight budget isnt worth it in 2027 especially with other young arms that need more MLB innings.

FREE AGENTS

No. 1: Clay Holmes 2 years 40 mil. 3rd year team option for 25 mil with a 5 mil buyout... 17 mil in 2027 then 23 mil in 2028. Holmes will serve nicely as #2 or #3 starter on a competitive white Sox team and he already is accustomed to Chicago.

TRADES

Logan Webb for Billy Carlson, Jaden Fauske, David Sandlin, Anthony Kay, and Christopher Oppor. From the Sox perspective they get their workhorse front of the rotation type starter. Bonus Webb is on a pretty friendly deal that will pay him 18 million each of the next two seasons. From the Giants perspective they are in absolute hell a mid 60s win total and a bunch of bad contracts with little help on the horizon. The farm system is good but has mostly younger prospects years away. The big league club needs to start shedding contracts and assets and Webb is one of their if not their biggest asset. He nets the Giants a top 100 prospect in Carlson who adds to their already solid group of young middle infielders, an intriguing teen OF'er, a high octane arm in Sandler who can immediately give their staff innings at the big league level, a versatile P in Kay on just a 5 mil deal who they could look to spin at the deadline, and oppor who was a very promising arm in 2025 but fell apart in 2026 that they can take their time with and try to right the ship. Some may think this is a little light from the Sox side but Webb has a lot of miles on that arm and by his standards 2026 was a down year, the Giants are best off grabbing a big package for him now than risking a further performance decline or any type of injury that would hurt his value.

SUMMARY

C Teel
1b Mune
2nd Meidroth
SS C. Montgomery
3rd Vargas
LF Antonacci
CF Peters
RF B. Montgomery
DH Benintendi

Bench OF Grichuk
Bench OF Doyle
Bench UTIL Baldwin
Bench C Quero

The lineup is what it is, With limited resources my best approach is to hope the high K guys improve while keeping their elite power and that some of the younger over achievers simply continue to overachieve. The big addition to this group in 2027 is likely Caleb Bonemer at some point in June or July, he should see immediate at bats in games vs lefties where some of the white Sox hitters tend to struggle and if he proves himself as an everyday regular the Sox can then entertain bigger deals for Colson or perhaps letting Mune walk if the k problems persist. Some times the best move you can make is not making one.

  1. Webb
  2. Holmes
  3. Burke
  4. H. Smith
  5. Castillo (see how spring goes, would not be scared to cut him if and when need be)

Closer- Taylor ( I would have loved to let him start but one more year as an elite pen arm works)
RH Hicks
LH Hudson
RH Brazoban
LH Schultz- (new newbcomb role)
RH Martin - (new fedde role)
RH Vasil
RH McDougal

This staff gets a big boost with the usage of both my primary signing and primary trade shoring up the front end. The Sox got a lot out of openers and mixing and matching but at the end of the day if you really want to compete in October on a consistent basis you need the horses. Sox also will hopefully have some depth with a AAA rotation featuring Thorpe, S.Smith, Cannon, Bush among others.

This 26 man roster should come in between 132-134 mil, just over budget but nothing too crazy for a big market team coming off a playoff run. While I added some money to the 2028 ledger with bigger contracts coming off the books this team still has tons of financial flexibility for the up and coming season to add via trade, free agency, or simply keep their in house talent.