Anthony Kay Signs Two-Year Contract with Chicago White Sox

date: 2025-12-03 17:06:00,

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 Gerald 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 Poncewhat 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 David 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.

What are the financial implications for the White Sox if Anthony Kay successfully triggers his performance-based incentives?

Deal Details & Contract Breakdown

On December 3rd, 2025, the Chicago White Sox announced they have signed left-handed pitcher anthony Kay too a two-year contract. While financial details haven’t been officially disclosed, sources indicate the deal is worth approximately $6 million, with a potential for performance-based incentives. this move bolsters the White Sox’s pitching depth heading into the 2026 season.The contract includes a club option for a third year.

* Contract Length: 2 years

* Estimated Value: $6 million (plus incentives)

* Club Option: Included for the 2028 season

* Position: Left-Handed Pitcher

Kay’s Career Trajectory & Performance

Anthony kay, 29, has bounced around several organizations throughout his MLB career, including the Toronto Blue Jays, New York Mets, and most recently, the Kansas City Royals. He’s shown flashes of potential but has struggled with consistency and injuries.

Here’s a look at his career stats (as of December 3, 2025):

* MLB Games Pitched: 68

* Career ERA: 4.88

* Career WHIP: 1.45

* Strikeouts: 228

* Walks: 115

His best season came in 2021 with the Blue Jays, where he posted a 4.06 ERA in 63.1 innings pitched. He primarily functions as a swingman, capable of both starting and relieving, a valuable asset for any team. Analyzing his pitch repertoire reveals a fastball averaging 92 mph, a slider, and a changeup.Improving command of his off-speed pitches will be key to his success in Chicago.

white Sox Pitching Staff Impact

The addition of kay addresses a need for left-handed pitching in the White Sox bullpen and provides starting pitching depth. Chicago’s rotation currently features[mentioncurrentprojectedstarters-[mentioncurrentprojectedstarters-research needed for accurate names], and Kay will likely compete for a spot in the back end of the rotation or serve as a long reliever.

* Increased Left-Handed Options: Kay adds a valuable left-arm to a staff that could benefit from more versatility against opposing lineups.

* Rotation Depth: provides insurance in case of injuries to starting pitchers.

* Bullpen Flexibility: Capable of eating innings in relief, offering manager[mentionmanager’sname-[mentionmanager’sname-research needed]more options.

Potential Role & Expectations for 2026

The White Sox are likely hoping Kay can rediscover the form he showed in 2021.His ability to limit walks and generate strikeouts will be crucial.

Here’s a breakdown of potential scenarios:

1. Rotation Spot: If he performs well in Spring Training, Kay could earn a spot in the starting five.
2. Long Relief: More realistically, he’ll likely begin the season as a long reliever, providing valuable innings out of the bullpen.
3. Spot Starter: He’ll be available to fill in as a spot starter when needed due to injuries or scheduling.

Kay’s Scouting Report & Strengths/Weaknesses

Scouts consistently praise Kay’s stuff, notably his fastball and slider. Though, his biggest challenge has been consistency and command.

Strengths:

* Good velocity on fastball

* Sharp slider with good movement

* Versatility (starter/reliever)

* Competitive attitude

Weaknesses:

* Command issues (high walk rate)

* Inconsistency in pitch location

* Susceptible to home runs

Impact of New Pitching Coach [Research Needed]

The White Sox recently hired[NameofPitchingCoach-[NameofPitchingCoach-research needed]as their new pitching coach. Kay will be working closely with him to refine his mechanics and improve his command. This coaching change could be a significant factor in Kay’s success with the White Sox.The new pitching philosophy emphasizes[mentionpitchingphilosophy-[mentionpitchingphilosophy-research needed], which could align well with Kay’s skillset.

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