After reestablishing his value post-Tommy John surgery, Lucas Giolito checks every box the White Sox are still looking to fill in their rotation.
I’m not usually one for romanticized reunions with players from years past.
More often than not, those moves don’t work out. For better or worse, there’s usually a reason a player moved on in the first place. Maybe the team traded him despite his wishes. Maybe he was fed up and wanted out in free agency. Maybe it was a money play. Or maybe it was something in between — a mutual decision rooted in timing.
But back in 2023, the Chicago White Sox traded Lucas Giolito at the deadline to the Los Angeles Angels.
Giolito was explicit at the time. He wanted to remain in Chicago and finish the season with the White Sox. The organization, however, knew its competitive window was closing, and Giolito represented one of its best opportunities to acquire meaningful prospect capital for the next iteration of the rebuild.
In fairness to ex-GM Rick Hahn, the move worked. Trading Giolito and Reynaldo López to the Angels brought back catcher Edgar Quero — now a member of the big-league club and one of the more promising young players on the roster.
Still, that didn’t make the trade sting any less for some fans.
Giolito marked the end of an era. He was one of the cornerstone prospects of the previous rebuild, a pitcher White Sox fans watched improve year over year. He broke out with an All-Star season at age 24 in 2019, threw a no-hitter in 2020, and followed it up with another strong campaign in 2021 that helped Chicago capture its first division title since 2008.
At the time, Giolito spoke openly about his loyalty to the organization and his teammates. His father even told local radio that Lucas wanted to spend his entire career with the White Sox.
I think a lot of fans wanted that, too. But that’s not always how the business works.
After the trade, Giolito struggled down the stretch with both the Angels and the Cleveland Guardians in 2023. Sometimes the glamorized “change of scenery” has the opposite effect, and that seemed to be the case.
Still, he got paid. Teams were hesitant to fully trust him, leading to a shorter-term deal, but a two-year, $38.5 million contract with the Boston Red Sox was a solid payday.
Unfortunately, Giolito felt discomfort in his right elbow during March of 2024. Soon after, Boston announced he had undergone Tommy John surgery to repair a partially torn UCL, sidelining him for the entire season.
Fast forward to 2025, and Giolito reestablished his value.
He returned to the mound, posted a 10–4 record with a 3.41 ERA, and logged 145 innings for Boston. Now, at 31 years old, he’s once again hitting free agency — this time with momentum.
And while I don’t typically romanticize reunions, this one feels different.
The White Sox no longer employ Ethan Katz — Giolito’s high school pitching coach and a key voice during his prime years in Chicago — but the organization still presents an appealing landing spot for a pitcher in Giolito’s position.
This is a young, energetic roster. The negativity and malaise of previous seasons are gone. The current core shows up ready to work and ready to play together.
The organization is also clearly trending upward. Chicago has spent real money this winter, generating excitement both locally and across the league.
What’s still missing, though, is a veteran starting pitcher — someone who can eat innings, stabilize the rotation, and protect the younger arms in the system.
That was a stated priority for GM Chris Getz this offseason. While I like the upside flyer on Anthony Kay, that move alone wasn’t the addition Chicago had in mind. Getz himself has said the team isn’t done.
Sean Newcomb feels far more likely to settle into a long-relief role, even if he’s stretched out as a starter in spring training. And we already know the White Sox have been aggressive in pursuing a mid-tier starting pitcher.
Giolito fits that mold.
Spotrac projects a contract similar to the one he signed with Boston — roughly $20 million in AAV. Maybe it’s two years, maybe three, but I wouldn’t push it to three years and $60 million in this market. If healthy, Giolito is a very solid middle-of-the-rotation arm with flashes of upside.
It’s also worth remembering that pitchers often take time to fully look like themselves after Tommy John surgery.
That was evident early in 2025, when Giolito allowed 24 earned runs over his first 33.2 innings. His ERA sat at 6.42 in early June.
From that point on, though, he looked like a different pitcher.
Over his final 111.1 innings, Giolito went 9–3 with a 2.51 ERA. The Red Sox went 14–5 in games he started.
If that’s the version of Giolito the White Sox would be getting in 2026, a rotation built around him, Shane Smith, and Davis Martin suddenly has a strong foundation. Anything contributed by Anthony Kay or the wave of young arms in the upper minors would be gravy.
Just because a player once wore a White Sox uniform doesn’t mean he makes sense for the future. But this isn’t about nostalgia.
It’s about fit.
Giolito has recently been spotted back in Chicago — working out, throwing, and even attending a Blackhawks game at the United Center. It’s clear he still enjoys the city. And if the White Sox make a competitive offer in free agency, a return to the South Side might make sense for both sides.
This is the type of move that would put a perfect bow on what has already been a surprisingly active offseason in Chicago.