The Major League Baseball GM meetings will commence in Las Vegas this week, as front office executives from all 30 teams converge for offseason meetings. In a typical offseason, these meetings don’t feature a ton of offseason activity, but instead lay the groundwork for future moves. With the lockout coming, however, this week could feature more advanced conversations surrounding free agents and trades, and it’s possible that a few deals could get done. When looking at free-agent targets for the White Sox, a handful of former Cubs could make some sense to pursue. Here are six of them.
MLB team officials have told me in recent days that their trade conversations are more advanced than is typical by this point in November.
— Jon Morosi (@jonmorosi) November 8, 2026
The GM Meetings are often a venue for preliminary talks, but it would not surprise me if there is a deal or two this week.@MLBNetwork
RHP Clay Holmes
The White Sox were heavily tied to Mets righty Clay Holmes in rumors ahead of the trade deadline before he was ultimately dealt to the Cubs. Despite not posting great numbers during his stint on the North side, Holmes was expected to decline his player option for 2027 and he did just that, hitting free agency ahead of his age-34 season. Overall, he’s posted excellent numbers in two years since becoming a starter, with a 3.53 ERA in 2025 and a 3.29 mark in 2026, so teams can rely on him as a solid mid-rotation arm moving forward. It’s very possible that the White Sox will renew their interest in Holmes on the free agent market and pursue a deal here.
RHP Kevin Gausman
Speaking of players tied to the White Sox at the deadline, Kevin Gausman was viewed by many as a perfect fit for the White Sox rotation. A veteran who has a history with White Sox pitching director Brian Bannister, Gausman had a down year by his standards in 2026, but has been one of the more consistent starters in baseball for the past few years. Gausman will be 36 in January, so his age could be a concern, but if the White Sox feel like they can bring the best out in him, he could be a target on a short-term deal. Gausman included the White Sox on his no-trade list on his previous contract, but the organization is in a much different place than it was then, so it’s unclear what his interest level may be.
OF Seiya Suzuki
MLB.com’s Scott Merkin reports that in addition to pitching help, the White Sox could pursue right-handed outfield help. Which tier they’ll be shopping in is not yet clear, but there’s perhaps no better one on the market than Suzuki. The 32-year-old slugger would require a significant financial commitment, but it may be worth it for a player who has posted an OPS over .800 in each of the past four seasons. He’d be a huge boost to the White Sox lineup, but would also require surrendering a draft pick due to his qualifying offer. I think the chances of the White Sox seriously pursuing Suzuki is unlikely, but with the flexibility to be aggressive, I wouldn’t rule it out.
LHP Shota Imanaga
In each of his three seasons since coming to MLB from Japan, Shota Imanaga has posted an ERA under 3.80 and held hitters to a sub-.235 batting average. In two of three seasons, he’s surpassed 170 innings pitched. While Imanaga can struggle with the longball at times, he’s one of the best in baseball at throwing strikes, and his splitter is an elite offering. Imanaga would bring a steady left-handed presence to the White Sox rotation, and he likely wouldn’t cost an unreasonable amount. He’d also reunite Munetaka Murakami with his teammate from the 2023 World Baseball Classic.
LHP Matthew Boyd
An even cheaper left-handed option for the White Sox could be Matthew Boyd, who uses an excellent changeup to excel against right-handed hitters. Boyd will be 36 this season and struggled with a couple injuries in 2026, so I’d avoid having to rely on him to have a strong rotation, but the White Sox could be interested as a depth lefty option. When healthy, Boyd has posted solid numbers in each of the past three seasons with the Guardians and the Cubs.
OF Ian Happ
Ian Happ’s struggles against left-handed pitching make him less of a fit than someone like Suzuki, but he’s still been one of the more consistent outfielders in baseball over the past few seasons. He’s played at least 148 games in every season since 2021, won four Gold Gloves in left field, and posted an OPS over .730 in each year. Happ is a better left-handed hitter, so he doesn’t exactly fit the right-handed profile the White Sox could be looking for, but he’s still a consistent outfield option that could upgrade the team’s lineup, and he’d be more affordable than a player in the tier of Suzuki or Randy Arozarena.
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