Free-agent pitcher Anthony Kay and the Chicago White Sox are in agreement on a two-year contract, according to sources familiar with the deal.
Former Blue Jay Anthony Kay signs with White Sox
Photo credit: © Nathan Ray Seebeck-Imagn Images
Dec 3, 2025, 14:00 ESTUpdated: Dec 3, 2025, 13:52 EST
A former Toronto Blue Jay has found a new home in free agency.
On Wednesday afternoon, FanSided’s Mark Feinsand reported that Anthony Kay has signed a two-year deal with the Chicago White Sox worth $12 million.
Kay spent the past two seasons with Nippon Professional Baseball’s Yokohama DeNA BayStars. He helped the team win the Japan Series in 2024, authoring a 3.42 ERA and 2.84 FIP in 24 starts, or 136.2 innings. Kay improved in 2025, posting a 1.74 ERA and 2.55 FIP in 155 innings pitched, which is impressive even though NPB is in a dead-ball era.
Kay was originally drafted 31st overall in the 2016 draft by the New York Mets. Before the 2019 trade deadline, he and Simeon Woods Richardson were traded to the Blue Jays in exchange for Marcus Stroman. Woods Richardson was packaged alongside Austin Martin for José Berríos before the 2021 trade deadline, but Kay remained with the Blue Jays for several years and made his big league debut shortly after.
The left-handed pitcher pitched with the Jays in 2019, 2020, 2021, and 2022. In 2021, he pitched most of his innings with the Blue Jays, posting a 5.61 ERA and a 5.43 FIP in 33.2 innings pitched, with a 25% K% and an 11.5% BB%. Over the four seasons, Kay had a 5.48 ERA and 4.67 FIP in 70.2 innings pitched, with a 23.5 K% and 11.6 BB%.
On Dec. 16, 2022, Kay was designated for assignment to make room for Chris Bassitt, who had just signed a three-year contract (which recently ended). Before Christmas that year, Kay was claimed off waivers by the Chicago Cubs and spent the 2023 season with them and the Oakland Athletics with mediocre results.
Kay has improved since his first stint in the big leagues, and by signing with the White Sox, the 30-year-old left-handed pitcher will get opportunities with a team that sat toward the bottom of the Major League Baseball standings.
He’s the second American-born player to return from overseas, as Cody Ponce reportedly signed with the Blue Jays on Tuesday after spending the 2025 season in Korea.
Ryley Delaney is a Nation Network writer for Blue Jays Nation, Oilersnation, and FlamesNation. She can be followed on Twitter @Ryley__Delaney.