White Sox could help Phillies pursuit of Bo Bichette with this unconventional trade

With just over a month until Spring Training begins and many impact free agents yet to sign, MLB’s rumor mill is swirling steadily. Among the big names still on the market: Blue Jays star shortstop Bo Bichette. While rumors about a Toronto reunion and interest from AL East rivals Red Sox and Yankees have been around since the beginning of the offseason, a new team has entered the chat. The Philadelphia Phillies are reportedly meeting with Bichette early this week, but USA Today’s Bob Nightengale reports that any Phillies deal with Bichette would require some roster reshuffling. One such move could be a trade of veteran outfielder Nick Castellanos, who no longer has a clear role on the roster and is owed $20 million for 2026. I think a deal of the sort is worth considering for the White Sox, who could pull the trigger on a deal to help the Phillies, and themselves, out.

First off, it’s very unlikely that any team, let alone the White Sox, would take on the entirety of Castellanos’ salary. The Phillies know this, but they’ll hope for a team to take on some of the $20 million and likely wouldn’t command much in return. The White Sox could send an out-of-options player who may not make the team, like Korey Lee or Tyler Gilbert. In addition, a team like the White Sox may be more inclined to take on more of the contract if the Phillies include a prospect or two in the deal. If moving Castellanos means the Phillies can land a superstar in Bo Bichette, adding a couple prospects feels like a small price to pay to make it happen. Maybe something like Korey Lee for Castellanos and RHP Matthew Fisher, with the White Sox paying half the $20 million contract could get the job done. 

Castellanos bring a veteran presence looking for a bounce-back

In Castellanos, the White Sox would receive a mature veteran bat to add to their young lineup. 
He didn’t have his best season in 2025, posting a .694 OPS, but he slugged 17 home runs and 27 doubles, and adds some power from the right side. Castellanos will be 34 on Opening Day, and he’s a liability on defense at this stage of his career, but the White Sox could mix him in to right field and give him a steady number of at bats at DH. A previously down season in 2022 was followed by an all-star year in 2023, so Castellanos could always bounce-back in a contract year. Chris Getz previously indicated a desire to add mature bats to the White Sox lineup, but to this point, the only bats the White Sox have added are high-risk, high-upside players. A career .272 hitter with a .785 OPS, Castellanos could be exactly the type of veteran bat the White Sox are looking for. 

Adding a veteran bat and a prospect to the mix for a minimal return feels like a no-brainer for the White Sox, but it’s unclear whether the cost-savvy Jerry Reinsdorf would be open to such a deal. Realistically though, Castellanos is a more reliable bat than any outfielder the White Sox would sign on the free-agent market. Veteran options like Mike Tauchman or Michael Conforto could be of interest, but neither of them provide the offensive upside and track record of Castellanos.

If the White Sox intend to add another veteran bat to the lineup, it’s a worthwhile conversation to have. The opportunity to not only fill the outfield void, but also add another young player to the farm system may be too good to pass up. 

Chris Getz has work to do and he can, and should, look to an unconventional trade to get it done.