Last week, the Chicago White Sox made their first signing of free agency, inking left-handed starting pitcher Anthony Kay to a two-year, $12 million contract.

Kay reinvented himself in Japan, turning into a legitimate starting pitcher with the Yokohama DeNA BayStars in 2025. A refined six-pitch mix and a new usage pattern helped fuel his breakout season, and the White Sox pitching group should have plenty to work with as he transitions back to MLB.

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Ironically, as Kay arrives from the BayStars, two former White Sox players are heading to his old team.

Jose Ruiz — the right-handed reliever who pitched for the White Sox from 2018 to 2023 — signed a one-year deal with Yokohama that includes a 2027 club option. The agreement pays him $1.2 million guaranteed with another $200,000 available through incentives. Not bad for someone whose nightmare 2025 season looked like it might end his big-league career.

Ruiz has always had big stuff — a lively fastball with late run — but persistent control issues held him back during his time in Chicago. His best season came in 2021, when he posted a 3.05 ERA over 59 appearances for a White Sox team that won the AL Central. He rediscovered some form with the Phillies in 2024, but split last year between Philadelphia and Atlanta and finished with an 8.82 ERA.

The other surprising name signing with Yokohama: Dayán Viciedo. Yes, he’s still playing professionally despite not having an MLB plate appearance since 2014.

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Viciedo spent five seasons with the White Sox and topped 20 home runs twice. His most promising year came in 2012, when the 23-year-old launched 25 homers with 78 RBIs. But the swing-and-miss issues and defensive limitations ultimately kept him from sticking long-term in the majors.

After bouncing between the White Sox and Athletics’ minor-league systems in 2015, he went to Japan in 2016, signing with the Chunichi Dragons — where regular playing time and a guaranteed contract awaited. His NPB career has now lasted a decade, featuring 141 home runs and an .810 OPS.

Viciedo played 48 games for the BayStars in 2025 — making him a teammate of Anthony Kay — and Yokohama is bringing him back again for 2026.

Seeing his name pop up again is a fun flashback for Sox fans — and the timing couldn’t be more ironic, considering Chicago just signed a pitcher from the very same team.