Just before the Winter Meetings, the Chicago White Sox woke up from their offseason slumber, signing starting pitcher Anthony Kay to a two-year contract in free agency.
Free-agent pitcher Anthony Kay and the Chicago White Sox are in agreement on a two-year contract, according to sources familiar with the deal.
— Robert Murray (@ByRobertMurray) December 3, 2025
Kay has had a fascinating baseball journey, one which culminated in him dominating the NPB in Japan last season to the tune of a 1.74 ERA in 155 innings. He spurned larger offers to return to Major League Baseball, receiving $12 million total from the White Sox (or $20 million, if his $10 million mutual option for 2028 is accepted by both parties).
It's a nice addition by general manager Chris Getz, as the team has money to burn and desperately needed a left-handed presence in the rotation behind the triumvirate of Shane Smith, Davis Martin, and Sean Burke.
Of course, Kay, 30, shouldn't be considered a long-term piece for the White Sox. This team is still rebuilding, and more moves like this one are necessary in order for the Pale Hose to speed up the process.
White Sox must double-down on Anthony Kay signing by bringing in more veterans on short-term deals
By way of signing a two-year deal, it isn't unthinkable that Kay could make it through the entire 2026 season in a White Sox uniform. However, if he translates his success in Japan back to the majors in the first half of next season, the South Siders seriously need to consider flipping him for prospects at the trade deadline. It's a very similar approach to the one the team took with RHP Erick Fedde in 2024.
It's no secret the White Sox failed on that front this past year, completing just two trades while surprisingly holding onto some of their best assets, including outfielders Mike Tauchman and Luis Robert Jr.
Barring a genuine long-term signing of a player designed to be added to the core of the team, the White Sox need to continue adding players like Kay: veterans with talent who can be traded.
All rebuilding squads go through this process, but Chicago's lack of notable trade chips besides Robert and Kay is frustrating. They don't need to sign someone like Alex Bregman to a bloated one-year deal; instead, adding a myriad of contributors looking for a major-league contract could yield two or three more pieces to deal by the time July 31, 2026 rolls around.
That could include players trying to stick it out in the big leagues (Carlos Santana, Justin Turner), players trying to rehab their value after an injury-plagued campaign (Nestor Cortes) or former top prospects looking for new homes (Alexander Canario).
Kay was a nice start, but the White Sox cannot be done adding this offseason. Their trade deadline haul depends on it.