The 2026 World Series will be wrapping up this week, and the offseason is set to begin in the next few days. In what’s expected to be a busy November due to the impending lockout, the White Sox will certainly be on the hunt for starting pitching upgrades. MLB insider Jim Bowden released his top 40 free agents heading into the offseason, as well as a few teams who are the best fit for each. The White Sox are linked to a handful of pitchers, so let’s take a look at which they should target and which they’d be better off avoiding
LHP Tarik Skubal, LAD
Easily the best free agent on the market at any position this offseason, the two-time Cy Young winner will hit the open market ahead of his age-30 season and is expected to land a massive new contract. So why are the White Sox on this list of best fits? Well, the need for a frontline starter couldn’t be more obvious, and the team’s payroll is among the bottom in the league. In theory, a pursuit of Skubal could make sense. In reality, Skubal is going to sign with a big market team for an unreasonable amount of money, and the White Sox are unlikely to compete in that market. It would be an incredible upset if the White Sox are even a factor in the Skubal sweepstakes, as much as it would be fun to dream.
Verdict: Target, but they won’t.
RHP Freddy Peralta, TB
Aside from Skubal, the best starter on the market could be former Brewers ace Freddy Peralta, who struggled against his former team in Game 3 on Monday. It was a tale of two halves for Peralta in 2026, who struggled with the Mets and pitched much better down the stretch following a deadline trade to the Rays. Aside from the first half of 2026, Peralta has posted excellent numbers throughout his career as a starting pitcher, so it’s reasonable to assume his issues were an outlier. If the White Sox are going to spend big on a pitcher, Peralta could be the preferred option. He’s the same age as Skubal and could command a more reasonable contract. Peralta is my dream target for the White Sox.
Verdict: Target
RHP Clay Holmes, CHC
A popular name in White Sox trade rumors at the deadline, Holmes is once again linked to the White Sox here. The 33-year-old right-hander missed time with a fracture in his leg after a comebacker but pitched well when he was available last season, posting a 2.39 ERA before the trade and a 4.25 ERA after. Holmes is on the older side, but he’s a sinker-baller that heavily relies on ground balls, and that’s a skillset that can hold up well with age. Perhaps a two or three year deal would make sense, and he’s a solid option for teams looking for high-floor rather than high-ceiling arms. He wouldn’t be my first choice for the White Sox, but they could definitely do worse
Verdict: Target if other options are off the board
LHP Foster Griffin, CLE
Lefty Foster Griffin was one of the biggest success stories coming from Japan this offseason. The 30-year-old lefty came back to the states and joined the Nationals on a one-year deal, where he posted a 3.06 ERA in 22 starts before a deadline trade sent him to the Guardians. Griffin wasn’t as dominant down the stretch with Cleveland, holding a 5.19 ERA in nine starts, though he was effective in the playoffs. He’ll now look to parlay his strong showing into a multi-year deal. Personally, I have a hard time trusting his good start when he faltered down the stretch and relies more on command than stuff. There are other lefty options I’d prefer, like the guy who comes in next on this list.
Verdict: Avoid
LHP Trevor Rogers, BAL
A former Rookie of the Year who has struggled to stay healthy at times in his career, Rogers finally put together a healthy and productive 2026, leading to the possibility the Orioles give him a qualifying offer. He posted a 4.03 ERA in nearly 170 innings and should be able to increase that workload even further in 2027. The underlying metrics on Rogers suggest there could be even more in the tank, and Rogers would be my top realistic lefty target for the White Sox this offseason. As long as they’re willing to potentially part with a draft pick, this is a guy who should be at the top of their list.
Verdict: Target
LHP Robbie Ray, SD
Another popular name in trade deadline rumors, Robbie Ray got off to a strong start this season and ended up dealt to the Padres in August. While the overall 3.59 ERA in 182.1 innings looks strong on the surface, Ray’s underlying numbers suggest some luck was involved, and he spent the entire season pitching at two of the most pitcher-friendly ballparks in the league. He’s now 35 years old and could be due for some stat regression in 2027, and going to a more hitter-friendly park like he would in Chicago is a recipe for disaster. I wouldn’t hate adding Ray as a second or even third addition to round out the rotation, but he wouldn’t be high on my list of targets.
Verdict: Avoid
RHP Kevin Gausman, CHC
I liked the idea of the White Sox trading for Kevin Gausman at the deadline, but his no-trade list that included the South-Siders made that slightly complicated. Instead, he ended up on the North side, where he didn’t improve upon his rough start in Toronto. Gausman had been the model of consistency prior to 2026, so it’s easy to chalk the season up as an outlier, but his age complicates things. Gausman will be 36 before Opening Day and saw some decrease in his splitter’s effectiveness, which is truly the pitch he needs to be successful. Like Ray, I wouldn’t be opposed to Gausman rounding out the White Sox rotation, but he shouldn’t be a main priority for the team.
Verdict: Target only if you miss on other options
Kevin Gausman strikes out the side to open his season! pic.twitter.com/9sCmKpGE5N
— MLB (@MLB) March 27, 2026
LHP Sean Newcomb, CWS
The only reliever linked to the team here and the most significant impending free agent for the White Sox this offseason, Newcomb was one of the most valuable bullpen pieces for the South-Siders this season. He’ll hit free agency and likely look to cash in with a multi-year deal, and the White Sox will be left with the decision of whether or not to pursue a reunion. As far as I’m concerned, they should be interested, and if they’re not able to get a deal done, replacing him becomes an offseason priority. I’m not sure what Newcomb’s asking price will be and I wouldn’t overpay, but I’d definitely be interested in bringing him back for the right cost.
Verdict: Target (or replace)
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