With the latest free agent contracts dished out to starting pitchers, the Chicago White Sox could get left behind before addressing their most obvious offseason need.
The Chicago White Sox got creative in addressing the club’s clear need for starting pitching this offseason.
In early December, Chicago agreed to terms on a two-year contract with left-hander Anthony Kay, who comes over from Japan after reworking his arsenal and reestablishing his value in Nippon Professional Baseball.
Kay is guaranteed $12 million on the deal. He’ll earn $5 million in both 2025 and 2026, with a $2 million buyout if his mutual option for 2027 is not picked up.
The White Sox desperately needed a lefty for the rotation, and Kay’s upside makes him an intriguing fit. He profiles as the type of pitcher who could benefit from working with Brian Bannister and the White Sox pitching lab and potentially exceed expectations.
But Chicago also made it clear they weren’t done adding to the rotation. Chris Getz said as much immediately after signing Kay, reiterating at the Winter Meetings that pitching would remain a priority. So far, though, nothing else has come to fruition.
I saw the writing on the wall with the closer market early. After seeing what experienced relievers were getting in free agency, it never felt realistic for the White Sox to pay for one of those arms.
That’s now become reality. Most of the proven closers have landed elsewhere, and the White Sox front office has effectively prepared the fanbase for their “big” bullpen addition to be someone without ninth- or even eighth-inning experience.
I could see something similar happening with starting pitching.
While Getz has said the White Sox plan to add more arms to the rotation, he may be biting off more than he can chew. The free-agent market has heavily favored players, far more than teams.
Cody Ponce landed a three-year, $30 million deal. He’s more proven than Kay, and while he was dominant in Korea—and, in my view, worth the gamble—the KBO is undeniably weaker competition than NPB.
Adrian Houser opened the 2025 season stuck in Triple-A before joining the White Sox and thriving. He was traded at the deadline to Tampa Bay, struggled down the stretch, and finished the season with a 3.31 ERA overall (4.79 with the Rays).
He still just signed a two-year, $22 million deal.
Dustin May has battled injuries his entire career and posted an ERA just shy of 5.00 in 2025. Even he secured $12.5 million from a Cardinals team that appears headed for a rebuild.
In this market, acquiring a quality starting pitcher means spending roughly $15 million per year.
How comfortable is Jerry Reinsdorf going to be with that?
It’s not a market that looks promising for the White Sox. They’ll almost certainly add someone for depth, but it’s increasingly likely to be another reclamation project or declining veteran rather than a starter with real upside.
A reunion with Lucas Giolito makes sense on paper, but he’s going to command more than $20 million annually. That’s simply not the financial pool Chicago plans to swim in.
This is the reality of free agency in the modern game. It requires teams to overspend, and as a result, the gap between the haves and the have-nots only continues to widen.
For now, the White Sox fall firmly into the latter category.