The White Sox and left-hander Anthony Kay are reportedly in agreement on a two-year, $12MM contract. The former first-round pick and top prospect, who’s represented by CAA, will be paid $5MM in each of the next two seasons and has a $2MM buyout on a $10MM mutual option for the 2028 season. He can earn another $1.5MM via incentives. Kay has spent the past two seasons pitching well for the Yokohama DeNA BayStars of Japan’s Nippon Professional Baseball.
It’s a familiar page in general manager Chris Getz’s playbook: sign a former first-rounder to a two-year deal on the heels of a strong run pitching in one of the top leagues in Asia.
That strategy worked out reasonably well when Chicago signed Erick Fedde for two years and $15MM in the 2023-24 offseason following a terrific season in the Korea Baseball Organization; Fedde was traded to the Cardinals in a three-team swap in July 2024, netting the White Sox Miguel Vargas and minor league infielders Alexander Albertus and Jeral Perez. Vargas was a league-average bat for the South Siders in 2025 and is controlled another four seasons. Albertus and Perez rank within the top 25 prospects in the Sox’ system.
The Sox will hope for similar results in their similarly priced investment into Kay. The 30-year-old southpaw (31 in March) has pitched 291 2/3 innings since heading to Japan. In that time, he’s logged a 2.53 ERA with a 20.9% strikeout rate, 7.9% walk rate and 54.5% ground-ball rate in 48 starts out of the BayStars’ rotation.
Kay has changed his pitch repertoire since moving to NPB. He sat 94.1 mph with a four-seamer, 87.9 mph with a cutter and 86.2 mph with a slider during his limited big league work from 2019-23. He’s added about three miles per hour to that cutter and also begun throwing a sinker that he didn’t have during his last run in North America, which he credits with generating more soft contact. He’s still throwing a sweeper and occasional changeup, and the lefty has also dabbled with a curveball. (He spoke about those changes and more in an October chat with Fansided’s Robert Murray.)
From 2019-23, Kay pitched 85 1/3 innings between the Blue Jays, Cubs and Mets. It was the Mets who originally selected him 31st overall back in 2016, though they were actually the third team for whom he pitched in the majors. New York traded Kay and Simeon Woods Richardson to the Blue Jays in exchange for Marcus Stroman back in 2019, and Kay made his MLB debut not long after the swap.
Things never clicked for Kay in the majors. He’s been tagged for a 5.59 ERA with a solid 22.4% strikeout rate but an ugly 12% walk rate. Opponents averaged 1.27 homers per nine innings against him. He didn’t fare much better in terms of run prevention in parts of four Triple-A seasons, logging a 5.40 earned run average in 148 1/3 innings pitched.
As we saw with Fedde and with yesterday’s three-year, $30MM deal between the Blue Jays and Cody Ponce, what Kay did in his prior MLB work holds virtually no bearing on his newfound payday. He’s a different pitcher now than he was at any point in 2019-23, and the White Sox are paying him based on the their belief that the changes he’s implemented while pitching in Yokohama will beget better results back in Major League Baseball.
There’s inherent risk, but at this price point, it’s also hard to fault a White Sox club that’s still in the midst of a rebuilding effort. Kay will either pitch well, at which point he’d emerge as a nice trade chip, or he’ll continue to struggle and the Sox will be out a relatively modest $5MM per season. The overall scope of this commitment is less than the $15MM paydays we saw for aging veterans in their late 30s/early 40s last year (e.g. Charlie Morton, Max Scherzer, Justin Verlander, Alex Cobb). It’s a life-changing deal for Kay but a small-scale gamble for the team.
Kay steps into a rotation mix that has plenty of options but is lacking when it comes to established contributors. Right-handers Shane Smith, Sean Burke and Davis Martin all pitched between 134 and 146 innings with ERAs between 3.81 (Smith) and 4.22 (Burke). None of the three has more than one full season of big league success. Smith was a Rule 5 pick at last year’s Winter Meetings and a rookie in 2025.
Those four are now favored to open the year in manager Will Venable’s rotation. Jonathan Cannon is tentatively penciled into the fifth spot for the time being, but he struggled greatly in 2025 and has minor league options remaining. Prospects Ky Bush and Drew Thorpe could be midseason options as they work their way back from Tommy John surgery performed last spring. Lefties Noah Schultz and Hagen Smith rank among the game’s top pitching prospects and could be ready at some point next summer as well.
There’s still room for the Sox to add some veteran innings. Getz has previously voiced a reluctance to commit to free agents beyond the 2026 season — though he did so with Kay, albeit in moderate fashion. There ought to be plenty of veteran arms looking at one-year deals, whether that’s a back-of-the-rotation innings eater (e.g. Michael Lorenzen, Patrick Corbin) or an upside play coming off an injury or poor performance (e.g. Nestor Cortes, Walker Buehler, Dustin May). The White Sox’ payroll currently projects at just $68MM, per RosterResource, so there’s room for Getz & Co. to bring in several additions to fill out the rotation, bullpen, outfield and infield.
Murray first reported that the two parties had agreed to a two-year, $12MM deal. The Athletic’s Will Sammon added details about the specific breakdown and incentives.