The White Sox became the first team ever to follow three consecutive 100-loss seasons with a playoff berth. They knocked out the Astros for their first series win in two decades in the Wild Card Series. It was an excellent season relative to expectations, though they surely feel they squandered an opportunity by failing to close out the Guardians after taking a 2-0 lead in the ALDS. How aggressive are ownership and the front office going to be to supplement a talented position player core?

Guaranteed Contracts

• Luis Castillo, RHP: $22.75MM through 2027 (deal includes ’28 vesting option at 180 innings)
• Munetaka Murakami, 1B: $17MM through 2027
• Andrew Benintendi, DH/LF: $14.5MM through 2027
• Jordan Hicks, RHP: $12MM through 2027
• Anthony Kay, LHP: $7MM through 2027 (including buyout of ’28 mutual option)

Option Decisions

• None

2027 financial commitments: $71.25MM
Total future commitments: $73.25MM

Arbitration-Eligible Players (service time in parentheses;  projected salaries courtesy of MLBTR contributor Matt Swartz)

• Joey Bart (5.020): $2.9MM
• Huascar Brazobán (3.170): $1.6MM
• Brenton Doyle (3.161): $3.6MM
• Miguel Vargas (3.101): $5.4MM
• Chris Murphy (3.055): $900K
• Jordan Leasure (2.161): $1MM

Non-tender candidates: Bart, Murphy, Leasure

Free Agents

• Erick Fedde, Sean Newcomb, Trevor Richards, Randal Grichuk, Jake Rogers, Tommy Pham

The White Sox entered the 2026 season in a rebuild. Despite a sour finish to the ALDS, in which they set an all-time record by striking out 21 times in a nine-inning shutout at the hands of Gavin Williams and three relievers, they’ve arrived. Now comes the hard part — elevating from talented upstarts to legitimate contenders.

Most of the work will be on the pitching staff. General manager Chris Getz acknowledged as much in his end-of-season press conference on Wednesday, not that Sox fans wouldn’t have known that either way. Chicago’s rotation was their weakest link all year and found itself in shambles by the playoffs. Sean Burke was their only reliable starter by season’s end. Everything else was a ‘Johnny Wholestaff’ game.

Even Burke tailed off a little bit down the stretch, but he was one of the better pitchers in the American League for most of the summer. He took the mantle of 2026 White Sox’ breakout starter, one which initially seemed would fall to Davis Martin. The Texas Tech product had a dominant 11 start run through May, then fell apart with a 5.63 ERA over his final 18 appearances.

Getz said that Martin was bothered by a right calf issue that probably had an adverse impact on his performance. His rotation spot still seems secure, but he’s hardly a sure thing to produce. The Sox need only look to their 2026 Opening Day starter, Shane Smith, as an example of how quickly things can go off the rails. Smith went from an All-Star rookie season to starting three MLB games this year, allowing 12 runs in 8 1/3 innings. He spent the remainder of the year in Triple-A, posting a 5.57 ERA with a 16% walk rate to plummet down the depth chart.

The rotation need was obvious enough that the Sox made what they believed was a stabilizing trade at the deadline. Chicago assumed Luis Castillo’s $22.75MM salary for next season in a trade that sent minor league catcher Boston Smith to Seattle. They offset some of the money by dumping the immediately ill-advised Seranthony Domínguez contract on the Mariners.

It was a buy-low move at the time, as Castillo carried a 5.06 ERA across 20 appearances. It nevertheless made a decent amount of sense. Castillo was clearly the odd man out with the M’s but should’ve provided some reliability for a pitching staff that desperately needed it. By eating next year’s salary, the Sox were able to make the move without paying much of a prospect cost. (Smith has good minor league numbers but hasn’t garnered much favor from scouts.)

Unfortunately, the early returns couldn’t have gone much worse. Castillo not only didn’t bounce back, he actively regressed. His velocity plummeted and he moved to the bullpen before being shut down with a shoulder impingement. Next year’s salary suddenly looks pretty far underwater, as it’s tough to imagine Castillo would command more than $8-10MM on a one-year deal if he were a free agent this winter. There’s also a vesting option for 2028, but the Sox presumably aren’t going to let him approach the necessary 180 innings next season unless his performance markedly improves.

Chicago would surely like a mulligan and should have Castillo’s name out there on the offseason trade market. It’s unlikely they’d find interest outside of another bad contract swap, so he’ll probably remain with the team into Spring Training. Castillo is penciled into a rotation spot for now but may not be among their top five arms come Opening Day.