The Chicago White Sox made their first move of free agency on Wednesday, signing left-handed pitcher Anthony Kay to a two-year, $12 million contract.

Kay has spent the last two seasons pitching professionally for the Yokohama DeNA Bay Stars in Japan, and a breakout 2025 campaign that included 155 innings pitched with a 1.74 ERA now gives him the opportunity to secure another payday and return to Major League Baseball.

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According to reports, Kay had more lucrative offers on the table in Japan than the two years and $12 million he accepted from the White Sox. But returning stateside was clearly a priority, and the White Sox pitching lab — led by director of pitching Brian Bannister — should give Kay the best environment possible to find big-league success.

If things go well, that could set him up for another strong contract a few years from now.

I already liked this signing for the White Sox. It’s a low-risk, high-reward move that brings balance to the starting rotation. But the contract details sweeten the pot even more.

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Chicago will pay Kay $5 million in both 2026 and 2027, keeping him under club control for at least two seasons. Then comes a $10 million mutual option for 2028. If that option isn’t picked up, there’s a $2 million buyout, bringing his total guarantee to $12 million.

Mutual options are rarely exercised — they essentially require the player to perform at the exact value of the option.

If Kay emerges as a strong mid-rotation starter, he’ll almost certainly be able to command more than $10 million on a one-year deal after 2027, so he’d have no reason to accept his half of the option. And if things don’t go well, the White Sox aren’t likely to pay $10 million for a pitcher who hasn’t earned that price tag.

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I wouldn’t bet on the 2028 option being picked up, but it’s a useful piece of the contract structure — especially if that extra layer of control enhances his trade value.

Depending on how the White Sox develop collectively and how competitive they are in 2026, having multiple years of club control gives Chicago options. They can use Kay to help them win games or use him to accelerate the rebuild via trade, much like they did with Erick Fedde when he returned to MLB from Korea.

A six-pitch mix from the left side, a fantastic ground-ball rate, and two to three years of team control? Sign me up.

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Anthony Kay joining the White Sox isn’t the story of the offseason. But how he pitches in the rotation might become one of the biggest variables in how their 2026 season unfolds.