The Chicago White Sox are clearly in the midst of a retooling phase, and their latest moves are a clear signal that the front office is thinking long-term-even if that means shaking up the current core. The biggest headline?
Trading away Luis Robert Jr., one of the most dynamic players on their roster. Robert wasn’t just a defensive anchor in center field-he was also a force at the plate, a true two-way talent who brought energy and production on a nightly basis.
In return, the White Sox landed Luisangel Acuña, a name that carries weight thanks to his All-Star brother, Ronald Acuña Jr., but one that’s starting to build its own reputation. Luisangel is expected to slide into center field for now, filling Robert’s shoes defensively.
But here’s where things get interesting: Acuña’s real value might lie in his versatility. He’s capable of playing second, third, and shortstop, giving the Sox a Swiss Army knife-type option who can move around the diamond depending on team needs.
That flexibility opens the door for some creativity in the outfield, and the White Sox are already making moves to solidify that picture. They’ve agreed to a one-year, $6 million deal with outfielder Austin Hays, which includes mutual options for 2027. Hays is the kind of steady, experienced presence this team needs-someone who can hold down right field and bring a bit of veteran stability to a young, evolving lineup.
As it stands, Chicago’s projected outfield could feature Andrew Benintendi in left, Hays in right, and Acuña in center. That’s a solid trio on paper, but it’s not necessarily set in stone. If the White Sox want to unlock Acuña’s full potential as a utility infielder, they may need another option to step up in center field-and they might not have to look far.
Enter Colson Montgomery.
According to reports, Montgomery is one of the most intriguing outfield prospects in the organization, and he could be knocking on the door of the big leagues sooner rather than later. A switch-hitting right fielder with legit pop and a cannon for an arm, Montgomery posted a .270/.360/.444 slash line with 12 home runs and 14 steals across 121 games last season.
Even more impressive? He climbed from Single-A to Double-A in his first full year of pro ball.
While he’s primarily been slotted in right field, Montgomery has the tools to handle center if needed. And for a White Sox team searching for long-term answers in the outfield, he could be a key piece of the puzzle. Adding a switch-hitter with power and athleticism to the lineup would be a welcome boost, especially for a team that ranked near the bottom in several offensive categories last year.
Montgomery finished the 2025 season as the organization’s fifth-ranked prospect, and while he doesn’t have a ton of professional experience under his belt, that won’t necessarily hold him back. If he puts together a strong spring, there’s a real chance he could break camp with the big club and make the Opening Day roster.
The White Sox are clearly laying the groundwork for something bigger. Trading a star like Robert Jr. is never easy, but it’s the kind of bold move that can help reshape a franchise. Between Acuña’s versatility, Hays’ reliability, and Montgomery’s upside, the outfield is starting to come into focus-and it might just be one of the more interesting position battles to watch as we head toward Opening Day.