Breaking down free agent outfielder Trent Grisham and a potential signing with the Chicago White Sox this winter.
In his recent piece ranking the top 50 MLB free agents this winter, insider Jim Bowden of The Athletic listed the Chicago White Sox as one of the potential landing spots for outfielder Trent Grisham.
The Yankees, Pirates, Rockies, Twins, and Angels were also mentioned as logical fits, but seeing Chicago in the mix raised some eyebrows.
With free agency set to open five days after the conclusion of the World Series, it’s a good time to start breaking down some of the available players and identifying who actually makes sense for the Sox to pursue. Grisham — along with a handful of other names linked to Chicago by Bowden — is as good a place to start as any.
So, how does this fit really look? Does Grisham align with what the White Sox are trying to build? And perhaps most importantly, is Jerry Reinsdorf actually willing to spend what it’ll take to land him?
The Player
Grisham broke out in 2025 with the New York Yankees, posting a career year in his age-28 season. He played 140 games in center field and launched 34 home runs — doubling his previous career high of 17 set back in 2022 with San Diego.
A two-time Gold Glove winner in center, Grisham brought serious defensive value to go along with his new-found power. He also crushed right-handed pitching, with 27 of his 34 home runs coming against righties and an .869 OPS in those matchups (compared to .652 against lefties).
That’s actually a reversal from earlier in his career, when Grisham’s splits were far more balanced. Still, the overall production can’t be ignored.
There's also some question about whether or not Grisham profiles best as an everyday outfielder or a platoon bat to face righties.
It makes his value tricky to gauge. On paper, a center fielder with a 125 OPS+ and elite defense should command a strong deal in free agency. But this breakout came after three rough seasons (2022–2024) where he hit just .191 combined.
The question every front office will ask: Which version of Trent Grisham are we getting?
The Contract
Spotrac projects Grisham’s market value at four years and $48 million, keeping him under contract through his age-32 season.
That would be a reasonable price for the numbers he put up in 2025 — but it comes with real risk. Teams will hesitate to hand out that type of deal to a player with such a volatile track record. Especially a team like the White Sox, who tend to be cautious in their spending and can’t afford to miss on one of their few major offseason swings.
Bowden had him at $30 million over two years, a higher AAV with less long-term risk for the club.
The Fit
On paper, the fit is there. Grisham complements the current White Sox core nicely. Assuming Luis Robert Jr. returns on his $20 million club option, Grisham likely slides into right field while Mike Tauchman shifts to a DH role, and occasional plays for Robert Jr. against right-handed pitchers.
If (or inevitably when) Robert goes down with another injury, Grisham can move seamlessly into center without sacrificing much defensively. That’s valuable insurance for a team that’s lacked stability in the outfield.
By 2027, both Robert and Tauchman could be gone. Andrew Benintendi won't be far behind. Meanwhile, outside of Braden Montgomery, there aren’t many outfield prospects close to the majors. A four-year deal for Grisham doesn’t block anyone and puts him right in line to contribute for the next contending team on the South Side.
If he even comes close to replicating his 2025 production, Chicago would be adding power, defense, and experience — all at a reasonable rate.
The Verdict
I actually love this fit. Grisham checks a lot of boxes for the White Sox without forcing them into the deep end of free agency — a place we all know they rarely swim.
At $12-14 million AAV, this is a deal Jerry Reinsdorf should be willing to make. The Sox need legitimate outfield help after losing Michael A. Taylor (retirement), Austin Slater (trade to Yankees), and Dominic Fletcher and Cory Julks (free agency), with Will Robertson claimed by Pittsburgh.
Replacing those players with more fringe AAA options would be a mistake. This front office needs proven big-leaguers who can help now and stay part of the core for the next few years. Grisham fits that bill perfectly.
The only concern is competition. If a team with deeper pockets jumps the market and pushes the total north of $60 million, the White Sox will be out. But if the price stays around $12-14 million for four years or less, Chicago should absolutely be in on Trent Grisham — and maybe even leading the charge.