The White Sox are heading into an offseason that figures to be shaped by pitching, and MLB insider Jim Bowden’s free-agent board gives them a pretty clear set of names to weigh. With the 2026 World Series wrapping up this week and the offseason set to get going in the next few days, the South Siders are looking at a market that includes frontline arms, bounce-back bets and a few older veterans who could help stabilize a rotation.
The biggest swing on the board is LHP Tarik Skubal, LAD. He’s the clear headliner among free agents at any position, a two-time Cy Young winner entering his age-30 season and positioned for a huge payday.
The White Sox make sense in theory because they badly need a top-of-the-rotation starter and their payroll sits near the bottom of the league. In practice, though, this feels like a long shot.
Skubal is expected to land with a big-market club on a massive deal, and Chicago probably won’t be in that lane.
Verdict: Target, but they won’t.
If the White Sox are serious about spending on pitching, RHP Freddy Peralta, TB looks like the cleaner fit. Bowden calls him the best starter on the market after Skubal, and there’s plenty to like in the profile.
Peralta had a rough first half in 2026 with the Mets before turning things around after a deadline trade to the Rays, and his career body of work says the ugly stretch may be the exception rather than the rule. He’s the same age as Skubal, but his contract should come at a more manageable number.
For Bowden, he’s the dream fit for Chicago.
Verdict: Target
Another name on the list is RHP Clay Holmes, CHC, who was already a familiar one in White Sox trade chatter during the deadline season. The 33-year-old right-hander dealt with a fractured leg after being hit by a comebacker, but he was effective when healthy, putting up a 2.39 ERA before the trade and a 4.25 ERA after.
His appeal is obvious: he leans on a sinker and a ground-ball approach that can age well. A two- or three-year deal could make sense, even if he isn’t the first choice for Chicago.
Verdict: Target if other options are off the board
Bowden also linked the White Sox to LHP Foster Griffin, CLE, but he’s not buying in. Griffin was one of the offseason’s better comeback stories after returning from Japan and signing a one-year deal with the Nationals, where he posted a 3.06 ERA in 22 starts before being traded to Cleveland. The finish wasn’t nearly as convincing - he had a 5.19 ERA in nine starts with the Guardians - and Bowden says he’d rather look elsewhere, especially given Griffin’s command-heavy profile.
Verdict: Avoid
The strongest left-handed fit after Skubal, at least in Bowden’s view, is LHP Trevor Rogers, BAL. Rogers finally put together a healthy and productive 2026, logging a 4.03 ERA across nearly 170 innings and putting himself in position to potentially receive a qualifying offer from Baltimore.
Bowden points to the underlying numbers as a reason there may still be more upside here. If the White Sox are willing to give up a draft pick, he sees Rogers as the top realistic lefty target on their board.
Verdict: Target
Another lefty who comes with both appeal and risk is LHP Robbie Ray, SD. He posted a 3.59 ERA in 182.1 innings after being traded to the Padres in August, but Bowden isn’t sold on the surface numbers.
The underlying performance suggests there was some good fortune baked in, and the fact that he spent the year in two of baseball’s most pitcher-friendly parks matters. Now 35, Ray could be due for regression, and a move to a hitter-friendly environment like Chicago could get ugly.
Bowden wouldn’t completely rule him out as a secondary addition, but he’s not high on the list.
Verdict: Avoid
RHP Kevin Gausman, CHC is another veteran Bowden would consider only in a supporting role. He liked the idea of the White Sox pursuing Gausman at the deadline, but the right-hander’s no-trade list, which included Chicago, complicated that possibility before he ultimately landed with the Cubs.
His 2026 season didn’t bounce back from the rough start he had in Toronto, and while Bowden is willing to treat it as an outlier given Gausman’s track record, age is a factor. He’ll be 36 before Opening Day, and the splitter that drives his success took a step back.
Bowden says he wouldn’t mind Gausman as part of the rotation, just not as a centerpiece.
The only reliever mentioned is LHP Sean Newcomb, CWS, and he may be the most important White Sox free agent of the bunch. Newcomb was one of the club’s most valuable bullpen pieces this season, and now he’s headed for free agency with a chance to secure a multi-year deal.
Bowden says Chicago should want him back and, if it can’t get something done, replacing him has to become an offseason priority. He wouldn’t overpay, but he would definitely be interested in a reunion at the right price.
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