The White Sox are dipping back into a familiar well – and hoping it pays off again.

Chicago has reportedly agreed to a two-year, $12 million deal with left-hander Anthony Kay, who’s spent the past two seasons reinventing himself in Japan with the Yokohama DeNA BayStars. The contract includes $5 million salaries in 2026 and 2027, a $10 million mutual option for 2028 with a $2 million buyout, and another $1.5 million available through incentives. For a rebuilding club looking for upside plays, this is a calculated swing – and if recent history is any indication, it’s one that could pay dividends.

We’ve seen this blueprint before from GM Chris Getz. Just last offseason, the Sox signed Erick Fedde to a two-year, $15 million deal after his breakout year in Korea.

That move turned into a win: Fedde pitched well enough to be flipped to the Cardinals in a three-team trade that netted Chicago a controllable bat in Miguel Vargas and two intriguing infield prospects, Alexander Albertus and Jeral Perez. Vargas gave the White Sox league-average production in 2025 and remains under team control for four more seasons, while Albertus and Perez now rank among the organization’s top 25 prospects.

Now, the Sox are hoping Kay can follow a similar trajectory.

Kay, who turns 31 in March, has been a different pitcher since heading overseas. Over 291 2/3 innings in NPB, he posted a 2.53 ERA with a 20.9% strikeout rate, 7.9% walk rate, and a strong 54.5% ground-ball rate across 48 starts. That’s a far cry from the version of Kay we saw in his MLB stints from 2019 to 2023, when he struggled with command and consistency.

The transformation didn’t happen by accident. Kay has overhauled his pitch mix since his last big league appearance.

During his time stateside, he featured a four-seamer averaging 94.1 mph, a cutter around 88 mph, and a slider in the mid-80s. In Japan, he’s added nearly three ticks to his cutter and introduced a sinker that’s helped him generate softer contact and keep the ball on the ground.

He’s still mixing in a sweeper, a changeup, and even flashing a curveball at times. It’s a more complete, more confident version of the lefty who once flashed promise as a first-round pick.

That promise, of course, came back in 2016, when the Mets selected Kay with the 31st overall pick. He was part of the package sent to Toronto in the 2019 deal for Marcus Stroman, and he made his MLB debut shortly thereafter.

But over parts of five seasons with the Mets, Blue Jays, and Cubs, Kay never quite found his footing. He logged just 85 1/3 big league innings, posting a 5.59 ERA with a decent 22.4% strikeout rate but a bloated 12% walk rate and a home run problem (1.27 HR/9).

His Triple-A numbers weren’t much better – a 5.40 ERA across 148 1/3 innings.

But as we’ve seen recently – not just with Fedde, but with players like Cody Ponce, who just landed a three-year, $30 million deal with the Blue Jays after his own stint overseas – prior MLB struggles don’t necessarily define a player’s future. Kay isn’t the same pitcher he was in 2019-23. The White Sox are betting on the version they’ve seen in Yokohama – and at this price, it’s a reasonable gamble.

For Kay, it’s a life-changing deal. For the White Sox, it’s a low-risk, high-upside play.

If he pitches well, he becomes a valuable trade chip or a stabilizing force in a young rotation. If he doesn’t, they’re out $5 million per year – a modest investment for a team still in transition.

And make no mistake, this rotation is still very much a work in progress.

Right now, Kay slots into a group that includes right-handers Shane Smith, Sean Burke, and Davis Martin – none of whom have more than one full season of MLB success under their belts. Smith, a Rule 5 pick last winter, posted a 3.81 ERA as a rookie in 2025.

Burke and Martin were serviceable, finishing with ERAs of 4.22 and in that same range, respectively. Jonathan Cannon is penciled into the fifth spot for now, but he struggled last season and still has minor league options.

Beyond that, the Sox have reinforcements on the horizon – but they’ll need time. Prospects Ky Bush and Drew Thorpe are working their way back from Tommy John surgery and could be midseason options. Lefties Noah Schultz and Hagen Smith, two of the most highly regarded arms in the system, may be ready by summer if their development stays on track.

So yes, there’s still room – and likely a need – for more veteran depth. Getz has previously shown reluctance to hand out deals that extend beyond 2026, though Kay’s contract is a modest exception. With the payroll currently projected around $68 million, there’s plenty of financial flexibility to add more arms – whether it’s a steady innings-eater like Michael Lorenzen or a bounce-back candidate with upside like Nestor Cortes, Walker Buehler, or Dustin May.

In the meantime, Kay represents a smart, strategic addition. He brings experience, a revamped arsenal, and the potential to stabilize a rotation that’s still searching for long-term answers. For a White Sox team looking to rebuild with purpose, this is the kind of move that bridges the gap – and maybe, just maybe, opens the door to another win down the road.