White Sox Could Target Former Cubs Pitchers in Free Agency

The Chicago White Sox are going to be active in free agency as they pursue some of the top starting pitchers on the market. For many fans, it probably already feels like a foregone conclusion that the White Sox will land one of their top targets.

Pitchers like Freddy Peralta and Michael King, however, will be pursued by close to a dozen teams over the next few weeks. The White Sox need to be prepared for a reality in which they come up short in their pursuit of a top-tier starting pitcher.

What could a backup plan look like? I've already previewed a few underrated options for the White Sox that could offer some of the same upside at a cheaper price. But we should also be discussing four former Chicago Cubs pitchers.

The crosstown rivals have a few holes of their own to fill in the starting rotation, largely because they've lost a significant portion of their pitching staff to free agency. And the White Sox might want to consider signing one of these former Cubs pitchers to bolster their starting rotation depth for 2027.

Shota Imanaga is an underrated arm who once again put together a strong season in 2026. Imanaga went 11-10 with a 3.77 ERA over 32 starts for the Cubs.

Matthew Boyd was considered Chicago's ace for much of the last two seasons. He dealt with some injuries in 2026 but finished the year 10-5 with a 3.91 ERA. He'll be 36 by Opening Day, but he's shown with the Cubs over the last few seasons that he can still be a highly productive arm.

Clay Holmes was a popular name for the White Sox at the 2026 trade deadline, but the New York Mets instead dealt him to the Cubs, where he posted a 4.25 ERA over his final nine starts of the season. Combining his last two seasons since making the transition to a starting pitcher, Holmes is 18-16 with a 3.44 ERA.

Kevin Gausman would be a buy-low option. I wasn't particularly high on the acquisition when the Cubs traded for him from the Toronto Blue Jays at the deadline. And my concerns proved to be warranted when he posted a 4.83 ERA over his final nine games of the season. Still, Gausman has been one of the more reliable starting pitchers in baseball for many years now.

From 2021 to 2025 with the Toronto Blue Jays, Gausman went 62-47 with a 3.34 ERA over 158 starts. He's now thrown at least 174.2 innings in each of the last six seasons. If the White Sox are looking for a veteran presence and an innings eater at the back end of their rotation, Gausman could be an attractive option.

Each of these pitchers brings something different to the table. Boyd and Holmes have All-Star upside. Imanaga is a funky lefty who would give opposing hitters a different look from the current arms in the White Sox starting rotation. Gausman brings a veteran presence and a track record of reliably eating innings.

If the White Sox come up short in their pursuit of the top starting pitchers on the market, they may want to consider signing one or more of these former Chicago Cubs pitchers.