As the Phillies scramble to reshape their roster in pursuit of Bo Bichette, the White Sox have a chance to land an outfield upgrade — and prospects — in one savvy move.
As soon as the Philadelphia Phillies were eliminated in the NLDS — when reliever Orion Kerkering air-mailed a throw home instead of taking the easy out at first — it was obvious that major changes were coming.
The Phillies have had this core together for four seasons now, but they still haven’t won a World Series. Some years, like 2022, they’ve come closer than others. But as that group gets older, the pressure to restructure the roster is mounting.
Earlier this offseason, I floated the idea that the Chicago White Sox could take advantage of Philadelphia’s situation by targeting Phillies players set to hit free agency. At the time, names like Kyle Schwarber, Ranger Suárez, and even reliever Jordan Romano made sense.
Schwarber is now off the table after re-signing for five years and $150 million. And while the White Sox remain in the market for starting pitching, it’s been made abundantly clear they won’t be players for a top-of-the-market arm like Suárez.
But a new opportunity may have just opened.
According to Bob Nightengale of USA Today, the Phillies “are looking into the possibility of shaking up their roster and finding a creative way to add free-agent infielder Bo Bichette.”
Philadelphia has also been negotiating to bring back catcher J.T. Realmuto, but those talks have reportedly grown frustrating — another sign that change could be coming.
Bichette has been a cornerstone of the Toronto Blue Jays for seven seasons, and after his monster 2025 campaign — including a .348 average and .923 OPS in the postseason — contenders are lining up for his services, even if it means shifting him to third base.
But landing Bichette won’t be easy.
Nightengale reports that in order to make it happen, the Phillies would need to "cut off negotiations with Realmuto, trade third baseman Alec Bohm and his $10.2 million salary, find a team who would take right fielder Nick Castellanos and pay at least a small portion of his $20 million salary, and perhaps move others as well."
That’s where the White Sox come in.
Chicago still needs a corner outfielder, and right field remains wide open. Castellanos, in particular, could make sense — especially if the White Sox are able to extract additional prospect value in the deal.
If the Phillies are desperate enough to dump his contract, the Sox — a team with plenty fo payroll flexibility — could step in, take on most or all of the money he's owed, and have the pot sweetened with young talent.
That’s a rare win-win.
It would give the White Sox an immediate right-field solution — a veteran bat on an expiring deal who raises the floor of the 2026 roster — while also bringing in prospects to support the long-term rebuild.
Castellanos isn’t the player he once was. He struggled in 2025, hitting 17 home runs with 72 RBIs, a .250 average, and a .694 OPS. That’s a far cry from his peak, but even in a down year he would still represent a more proven offensive option than anyone currently projected to get regular at-bats in right field for Chicago.
And there’s precedent for a bounce-back.
Castellanos posted the same .694 OPS in 2022, his first year in Philadelphia. He followed that with an All-Star 2023 season, hitting 29 home runs with 37 doubles, 106 RBIs, 11 stolen bases, and a .788 OPS.
A rebound in 2026 is well within the realm of possibility. And even if it doesn’t come, Castellanos would still bring veteran stability, lineup protection for young hitters, and leadership in the clubhouse.
That’s before you even factor in the prospect return.
The Phillies have one of the deeper farm systems in baseball, and Chicago could target either young arms in the lower minors or position players closer to MLB readiness. The White Sox system is currently loaded with upper-level pitching and position players who are still years away — adding talent to either bucket would help balance the pipeline.
It would be an out-of-character move for an organization that’s often reluctant to take on $20 million for a declining veteran. But it’s exactly the type of modern, opportunistic thinking that GM Chris Getz has hinted at since taking over.
If the Phillies are looking to offload Nick Castellanos to chase a bigger prize, the White Sox should be ready to pounce.