Anthony Kay's long road from Ward Melville to key member of first-place Chicago White Sox
Chicago White Sox pitcher Anthony Kay throws in the first inning of a game against the Cleveland Guardians on July 3 in Cleveland. Credit: AP/Sue Ogrocki
CHICAGO — Anthony Kay’s road to full-time major-league starter was far from linear.
And it goes without saying, the journey for the lefthander, a product of Ward Melville High School who grew up a Yankees fan and will start for the White Sox on Tuesday night against Gerrit Cole, has been anything but easy.
“Maybe I took it for granted the first time around,” Kay told Newsday late Monday before his White Sox started a four-game series against the Yankees. “Being drafted high in the first round, you kind of expect to be in the big leagues for a long time. And then being DFA’d [designated for assignment] a bunch and then going to Japan kind of put it in a new perspective to kind of appreciate it a little bit more, be a little bit more grateful.”
Kay was a first-round pick of the Mets (taken 31st overall) in 2016 and had Tommy John surgery some four months into his professional career. He eventually made his major-league debut, at the age of 24, in 2019. But that was for the Blue Jays as he was part of the package the Mets sent to Toronto in the deal that netted them Marcus Stroman, another Long Islander, before the 2019 trade deadline.
And that was only the start of the peripatetic nature of Kay’s career as, after subpar seasons with the Blue Jays, mostly as a reliever, from 2019-22, the pitcher, now a waiver-wire claim specialist, spent time in 2023 with the Cubs, the Mets (again) and A’s organizations.
His options few, Kay was soon off to Japan, this time as a starter, from 2024-25. And it was there, with the Yokohama Bay Stars of the Japan Central League, where Kay began to find his footing.
Kay peaked last season when he posted a 1.74 ERA, a single-season Bay Stars record. But even that failed-reliever-to-standout-starter story wasn’t linear. Kay at first struggled in his adjustment to starter in Japan, unable to go as deep into games as he, and his team, would like. Starters in Japan, typically on an every-sixth-day schedule because teams employ six-man rotations, are expected to go seven or even eight innings, with 115-120-pitch outings the norm.
Kay decided to add a two-seam fastball (a sinker) to his repertoire, a pitch that helped him take advantage of hitters in Japan, where contact — rather than power, the case in majors — is stressed.
Kay subsequently produced a league-leading 57.8% ground-ball rate in 2025 to go along with the sterling ERA.
And that paved the way back to the big leagues for Kay, whom the White Sox last offseason signed to a two-year contract worth a guaranteed $12 million, a package that includes a $10 million mutual option for 2028 (with a $2 million buyout).
Kay, now 31, is a long way from his days as a touted prospect. He is an elder statesman of sorts for a young White Sox staff that has helped key a turnaround for a club that entered 2026 with low expectations. Kay is 7-4 with a 4.21 ERA in 21 outings (19 starts) for a White Sox franchise that suffered three straight seasons of 100-plus losses from 2023-25 but came into this series leading the AL Central at 55-49.
“I think he is one of the guys on our pitching staff that is setting the tone for going out there and being fearless,” White Sox second-year manager Will Venable said a day before Kay faced the Yankees back on June 17 (Kay allowed four runs and six hits over four innings in a 10-5 loss). “Going out there and attacking in any way possible. It may not always be pretty, it may not always be what they set out to do, but they’re going out and getting it done.”
Something Kay, at last, is doing at the sport's highest level.
“Once you’re up here, as a young guy I didn’t really have perspective of how hard it was I guess,” Kay said. “I think you feel like you belong here, you feel like you should be there no matter what. You feel like you earned it already. And then having to go back out and kind of earn it again in Japan made me realize to not take it for granted this time around.”
Erik Boland started in Newsday's sports department in 2002. He covered high school and college sports, then shifted to the Jets beat. He has covered the Yankees since 2009.
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