Building an optimistic 2026-2027 White Sox offseason plan heading into a pivotal winter

Each year around this time, all the major publications put together mock offseasons and other predictions for how the offseason ahead might go down. I didn’t do it last year, but with the White Sox contention window now open and plenty of payroll flexibility, there’s no time like the present. I’ll be honest, these predictions are a little bit on the optimistic side, but I think they’re still on the upper bounds of realistic. With the White Sox payroll predicted at $125 million for 2027 as of right now, I feel that there’s significant room to add, but I’ll keep it under $200 million and in the 10-12th range in MLB. 

Without further ado, here is my mock White Sox offseason: 

Tender: OF Brenton Doyle, C Joey Bart, RHP Huascar Brazoban, 3B Miguel Vargas

Non-Tender: RHP Jordan Leasure, LHP Chris Murphy

With Jordan Leasure set to miss the entire 2027 season after undergoing Tommy John surgery and Chris Murphy’s inconsistency and control issues, that pair of hurlers are prime candidates to be non-tendered this offseason. Miguel Vargas is a no-brainer to tender, but Doyle, Bart, and Brazoban can all be useful players on the 2027 club, so I’d tender them as well. Doyle is a good platoon partner for Tristan Peters in center, Bart can fill the backup catcher role, and Brazoban is a useful reliever at his best. No decisions are too difficult here. 

Free Agents:

Sign RHP Freddy Peralta- 5 years, $140 million

Possibly the second-best starter on the market this offseason, Peralta is my top target if the White Sox want to make a splash in their rotation. A rough first half could put him right in range for the White Sox should they make an aggressive move to bolster their starting staff. His market is bound to be competitive, but The Athletic’s Jim Bowden predicts he’ll sign for $28 million a season, and the White Sox should have the payroll flexibility to make that happen 

Sign LHP Alex Vesia- 2 years, $16 million 

With lights-out reliever Sean Newcomb set to be a free agent and likely to cash in with a significant multi-year contract, the White Sox will need to find a replacement and may look for a cheaper way to do it. Enter Alex Vesia, who has spent the past several years quietly excelling in the Dodgers bullpen. Vesia has a ton of playoff experience and could be exactly the left-handed replacement for Newcomb the White Sox need at a much more affordable rate. 

Sign RHP Kevin Ginkel- 1 year, $4 million

A former 22nd-round pick turned into a solid middle reliever, Ginkel parlayed strong 2022 and 2023 seasons into some closing opportunities in Arizona but was never consistent. A big right-hander that pounds the strike zone, Ginkel could bolster the White Sox bullpen in the middle innings and make the bridge to Grant Taylor shorter. Bullpen help is always needed, especially if arms like Noah Schultz and Hagen Smith move back into the starting rotation. 

Sign OF Taylor Ward- 2 years, $30 million 

Outside the pitching staff, I expect the White Sox to explore upgrades to their outfield, and Taylor Ward may be the best value acquisition on the free agent market. True impact hitters like Randy Arozarena and Seiya Suzuki are going to be costly, and Ward is just one year removed from a 30-homer 100-RBI season with the Angels. His power took a step back in 2026, but he was among the league’s best in plate discipline. Should he put it all together in 2027, he could be a steal for the White Sox in the outfield. 

Sign OF Lane Thomas- 1 year, $2 million 

There was a time when many thought Lane Thomas was a future star in the league. At this point in his career, he’s a platoon outfielder that plays solid defense and hits left-handed pitching. In a role vacated by Randal Grichuk, Thomas could be the platoon pair for Sam Antonacci or Braden Montgomery and help bolster the outfield depth against southpaws. He has versatility to play several different positions and shouldn’t cost too much to sign. 

Sign IF/OF Jorge Mateo- MiLB deal 

If the White Sox are looking for a speed and defense threat to replace Luisangel Acuna on the roster, Jorge Mateo could be the answer. He’s one of the fastest players in all of baseball and can play several different positions. He generally doesn’t provide a ton offensively, but his versatility and occasional pop can be useful. In terms of utilitymen, you can certainly do worse, and Mateo is worth bringing in. 

Trades: 

Trade SS Billy Carlson, RHP Tanner McDougal, and IF William Bergolla Jr. to the Angels for LHP Reid Detmers

The White Sox were very involved in the Reid Detmers rumors at the trade deadline and they remain a great fit for the lefty, who is on the heels of a breakout season. Chicago would likely be unwilling to part with top prospects Caleb Bonemer or Roch Cholowsky, but the sides could center something around Billy Carlson and one of the White Sox young pitchers. Add in Bergolla, who could be ready to make his big league debut in 2027, and it may be enough to get a deal done. 

Trade DH Andrew Benintendi to the Diamondbacks for a PTBNL or Cash 

In a perfect world, the White Sox are able to dump Andrew Benintendi this offseason to free up the DH spot, but trading his salary is going to be difficult. Perhaps they’d be willing to consider little to no prospect return for Arizona to eat a little bit of Benintendi’s deal. Arizona’s designated hitters ranked last in baseball with a 77 wRC+ in 2026, so adding a league-average hitter against righties to platoon at DH could be an upgrade for them. 

Extensions: 

Sign 1B Munetaka Murakami- 5 years, $125 million 

The White Sox and Murakami are reportedly having ongoing discussions about an extension for the team’s leader in home runs in 2026. Murakami’s slump toward the end of the season may have lowered the price here, and it may be the best thing for the White Sox, who would love to keep him around long term. With Murakami entering a contract year in 2027, I expect this to be a priority this offseason and I expect it to get done sooner rather than later. 

Here is how the White Sox roster would look after these moves, with a payroll that sits in the $190-$200 million range depending on the salary relief from the Benintendi trade and arbitration figures: 

Rotation: 

RHP Freddy Peralta
RHP Sean Burke 
LHP Reid Detmers
RHP Davis Martin
RHP Luis Castillo

Anthony Kay, Hagen Smith, David Sandlin, Noah Schultz, and Drew Thorpe are other options to take the spots of Martin and Castillo in the rotation, but as veterans who have had big league success, I’d give them the edge for now. 

Bullpen: 

RHP Grant Taylor (CL)
LHP Bryan Hudson
LHP Alex Vesia
RHP Jordan Hicks
RHP Kevin Ginkel 
RHP Huascar Brazoban
LHP Hagen Smith 
LHP Anthony Kay 

A few spots would be up for grabs here, but Anthony Kay and Hagen Smith could slide into the pen if they don’t make the rotation, with the free agent signings and returnees from last season filling out the rest of the group. Grant Taylor should begin and end the season as the team’s closer. 

Lineup: 

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

Bench: 

C Joey Bart
OF Lane Thomas
OF Brenton Doyle 
UTIL Jorge Mateo 

The White Sox often took advantage of platoon situations in 2026 and I’d expect that to continue with this group in 2027. Brenton Doyle and Lane Thomas would likely be in the lineup against left-handers, and Joey Bart and Kyle Teel could serve as a bit of a platoon behind the plate. Overall, this would be a well-balanced lineup with upside and some veteran presences. Top prospects Caleb Bonemer and Roch Cholowsky could be in line to join this group sometime during the summer as well.

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