Offseason Outlook: Chicago White Sox

The White Sox became the first team to follow three straight 100-loss seasons with a playoff berth. They knocked off the Astros for their first series win in two decades in the Wild Card Series. It was a great season relative to expectations, although they surely feel like they wasted an opportunity by failing to take down the Guardians after taking a 2-0 lead in the ALDS. How aggressive will ownership and the front office be in rounding out a core of talented players?

Guaranteed contracts

Option decisions

Financial commitments 2027: $71.25 billion
Total future commitments: $73.25 million

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

Non-tendering candidates: Bart, Murphy, Leasure

Free agents

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 during a nine-inning shutout at the hands of Gavin Williams and three relievers, they arrived. Now comes the hard part: going from talented rookie to legitimate contender.

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

Even Burke slowed down a bit down the stretch, but he was one of the best pitchers in the American League for most of the summer. He assumed the starting role for the White Sox in 2026, a role that initially seemed to fall out of favor. David Martin. The Texas Tech product had 11 dominant starts through May, then slumped to a 5.63 ERA over his final 18 appearances.

Getz said Martin was hampered by a right calf problem that likely negatively impacted his performance. His place in the rotation still seems assured, but he’s not sure he’ll produce. The Sox only have to look to their 2026 Opening Day starter, Shane Smithas an example of how quickly things can go off the rails. Smith went from an All-Star rookie season to 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 fall on the depth chart.

The need for rotation was obvious enough that the Sox made what they believed to be a stabilizing trade at the deadline. Chicago assumed That of Luis Castillo $22.75 million salary for next season in trade that sent minor league catcher Boston Smith in Seattle. They made up some of the money by getting rid of immediately ill-advised measures Seranthony Dominguez contract on the Mariners.

This was a buy-low decision at the time, as Castillo had a 5.06 ERA in 20 appearances. It made some sense, however. Castillo was clearly an odd man out with the M’s, but he should have provided some reliability to a pitching staff that desperately needed it. By eating into next year’s salary, the Sox were able to take the plunge without paying a lot of potential fees. (Smith has good numbers in the minor leagues but hasn’t gotten much favor from scouts.)

Unfortunately, the early returns couldn’t have been much worse. Castillo not only did not rebound, he actively regressed. His velocity dropped and he moved to the bullpen before being shut down due to shoulder impingement. Next year’s salary suddenly seems pretty underwater, as it’s hard to imagine Castillo would make more than $8-10 million on a one-year deal if he were a free agent this winter. There is also a vesting option for 2028, but the Sox likely won’t let him approach the needed 180 innings next season unless his performance improves noticeably.

Chicago would surely love a mulligan and should have Castillo’s name on the offseason trade market. They’re unlikely to find any interest outside of another bad contract swap, so he’ll likely stay with the team until spring training. Castillo is slotted into a rotation spot for now, but he may not be a top-five weapon on opening day.

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