As MLB free agency gets rolling this week, many teams around baseball begin negotiations to improve their team for 2026 and beyond. The White Sox are no exception. Although GM Chris Getz threw cold water on the idea of signing any free agents to a long term contract, he made it clear that the White Sox will be looking to improve their team in 2026. Almost every team in baseball will be on the hunt for pitching upgrades, and the White Sox could certainly use a veteran starter or two to help eat innings for a young rotation. With several familiar names on the open market, it might even make sense for the White Sox to pursue a reunion with one of these pitchers.
RHP Lucas Giolito
It’s been rocky for Giolito since he left the White Sox in a 2023 trade that netted the team catcher Edgar Quero. The end of Giolito’s 2023 season was a nightmare, with an ERA well-above 6.00 between the Angels and Guardians down the stretch. Still, Giolito landed a solid AAV on a two-year deal with the Boston Red Sox in free agency. An elbow injury wiped out Giolito’s entire 2024 season, and he finally got back on the mound in 2025. It was a solid bounce-back year for Lucas, who posted a 3.41 ERA in 26 starts for Boston. More elbow soreness prevented Giolito from making a postseason start, but it doesn’t seem to be a concern long term, and he’s expected to be fully healthy heading into 2026.
Giolito will hit free agency again at age 31, and the White Sox could consider bringing him back if they’re open to a multi-year deal. Questions about his health and effectiveness could lower the market price, and it could be an opportunity for great value for a team looking to add stability without a significant financial commitment. Giolito’s level of interest in a return is unknown, but the right-hander is obviously familiar with the organization. The White Sox moved on from pitching coach Ethan Katz this offseason, who notably was Giolito’s coach in high school, so the obvious appeal is no longer there. If Giolito would consider a return to the place where he had the best years of his career, the White Sox should be open to the idea.
LHP Jose Quintana
It feels like Jose Quintana is on these lists every year, but the veteran lefty could be just what the young White Sox rotation needs. The soon-to-be 37 year-old Quintana has been a consistently effective arm for much of his big league career, which began with the White Sox back in 2012. After five and a half years in the White Sox rotation, Quintana was dealt to the crosstown Cubs for a trade package that included Dylan Cease and Eloy Jimenez. Quintana went through a rough patch from 2019-2021, but got himself back on track in 2022 and has been solid ever since. Quintana has consistently gotten batters out despite less-than-overpowering stuff, and the White Sox rotation could use a lefty to replace Martin Perez. It’s been eight years since Quintana has put on a White Sox uniform, and he’s played for seven teams in between, but 2026 could bring an opportunity to go back to where it all began. The move could make a ton of sense for both sides.
1.91 ERA since the All-Star break? Yeah, @jose_quintana24's good at pitching. https://t.co/Pz9oA4RtYn pic.twitter.com/0knDIJbh7U
— Chicago White Sox (@whitesox) August 22, 2016
RHP Chris Bassitt
Chris Bassitt’s Chicago origin story feels like a lifetime ago, but the 36 year-old was drafted by the White Sox back in 2011 and made his big league debut for the team in 2014. Bassitt started five games for the White Sox before being dealt to the Athletics in the deal that brought Jeff Samardzija to Chicago. It took Bassitt a few years to get going, but the right-hander emerged as a solid starting pitcher in Oakland from 2019-2021 before an equally-effective one year stint with the Mets in 2022. This landed Bassitt a three-year deal in Toronto where he put up solid numbers from 2023-2025. He’ll now hit free agency going into his age 37 season and will likely be looking for a short term deal and a chance to start. He may not get the innings he wants in Toronto, so he could be looking for a bigger role elsewhere. Bassitt would have an opportunity for innings on the South Side and could be a much-needed veteran presence in the White Sox rotation. If the opportunity is there for a reunion, both sides should consider it.
Whether the White Sox reunite with a former player or bring in someone new, it’s fair to assume the club will add some veteran pitching to help their young staff. As the White Sox look to continue their quest toward contention, the options are abundant.