The Chicago White Sox have made their first major-league free-agent signing of the offseason. On Wednesday morning, they agreed to a two-year, $12 million contract with left-handed pitcher Anthony Kay.

Kay, a former first-round pick by the New York Mets in the 2016 MLB Draft, was once a notable prospect who headlined the Marcus Stroman trade to Toronto. He made his MLB debut in 2019 and spent most of 2019–2023 with the Blue Jays, bouncing between Triple-A and the bullpen without ever locking down a consistent role.

Before the 2023 season, the Chicago Cubs claimed him off waivers, and he went on to pitch for both the Cubs and Mets that year—briefly returning to the organization that originally drafted him.

Over the last two seasons, Kay went overseas to rebuild his value, signing in Japan and giving himself a clean slate. It paid off.

Pitching for the Yokohama DeNA BayStars in 2025, Kay delivered a dominant season as a starter.

155 innings, a 1.74 ERA, a 0.98 WHIP, and 130 strikeouts. He’s not overpowering and he’s not a big swing-and-miss arm, but he now has a deep, well-sequenced arsenal that keeps hitters off balance. That’s the difference between the pitcher he was in MLB and the version of himself that thrived in Japan.

It was even a clear step forward from his 2024 season overseas. The biggest change? Pitch usage.

Kay drastically reduced his four-seam fastball rate, which he threw more than 50% of the time in 2024, and leaned instead on a cutter that posted a 30% called-strike-plus-whiff rate and a 6.5 expected pitch value. His two-seamer generated ground balls 85% of the time, while his sweeper became his put-away pitch in left-on-left matchups.

He also mixes in a changeup and a curveball—giving him a true six-pitch mix to bring back stateside for his second chance at MLB success.

The White Sox needed starting-rotation depth, especially with a group that is currently entirely right-handed: Shane Smith, Davis Martin, Sean Burke, and Jonathan Cannon. Kay adds balance, stability, and a uniquely versatile bag of pitches for Brian Bannister to work with.

I don't expect this to be Chicago’s only starting pitching addition, but Kay can safely be penciled in as one of the starting pitchers for this team in 2026 that brings some balance and a fun bag of tools for Brian Bannister to get working with. And at two years and $12 million, there’s very little downside for the White Sox—who have a recent track record of hitting on these types of low-risk contracts, with Erick Fedde as the most recent example.

This is a "White Sox special," and I actually mean that in the most complimentary way.