White Sox Linked to World Series Champion Pitcher in Free Agency

The Chicago White Sox are on the hunt for starting pitching. Free agency has been open for over a week now, and rumors are starting to pick up as the GM meetings take place in Las Vegas.

White Sox GM Chris Getz has not shied away from his team's needs, but it remains a bit of a mystery just how big of a fish the White Sox have their eyes on.

Getz's recent comments to the media indicate Chicago is looking for more than an innings eater this time around. In his words, it will be a pitcher for "the middle to the top of the rotation."

Could that be one of the top names on the market, like Freddy Peralta or Michael King? It's certainly possible. However, as I've detailed already, the demand will be high for premium starting pitching. It ultimately may be in a tier or two below that where the White Sox find their guy.

Still, there should be plenty of opportunities for the White Sox to get at least one starting pitcher with upside, if not more, and one of the first tangible reports has now surfaced. According to MLB Network insider Jon Morosi, the White Sox are among the teams interested in right-handed pitcher Dustin May.

May started the 2026 season with the St. Louis Cardinals and was traded to the Milwaukee Brewers at the deadline, where he ultimately won his second World Series title.

Between St. Louis and Milwaukee, May went 7-9 with a 4.70 ERA over 31 starts in 2026. He threw a career-high 145.2 innings, but some of the underlying numbers were concerning. May ranked in the seventh percentile in hard-hit rate and the 14th percentile in average exit velocity allowed. He also struggled against left-handed hitters, allowing a .755 OPS and issuing 42 of his 50 walks to lefties.

There were some encouraging signs, though. May's four-seam fastball averaged 96.9 mph, up from 95.4 mph in 2025, and his strikeout rate climbed from 21.1% to 23.2% while his walk rate fell from 9.6% to 8.1%. That's enough to make him an interesting back-end rotation option, especially if he can find a better way to attack left-handed hitters.

But would it be enough for the White Sox to consider their starting rotation solved? Not in my book. Adding May would be a shot at upside, but it leaves too many question marks if he's the only rotation addition the White Sox make in free agency.

Between Sean Burke and Grant Taylor, there's plenty of excitement surrounding White Sox starting pitching in 2027. There's plenty of upside, but there are also areas where the White Sox could stand to improve. What they need now is a reliable veteran. Just like Chris Getz said, someone who can pitch at the top or middle of a playoff rotation. Dustin May is not that guy.

For the right price, though, he could still be an intriguing addition. Spotrac's market value projection has May getting three years and close to $45 million. I don't think that's an accurate price tag, nor do I think it's one the White Sox should pay if it ends up being the number May commands.

I'd expect the White Sox to be linked to more starting pitchers over the coming days and weeks as the free agent market plays out. Getz has already announced he'll meet with super agent Scott Boras during the GM meetings. Japanese right-handed pitcher Kaima Taira, who's a Boras client, could be a name for White Sox fans to watch.