As the baseball world gears up for the Winter Meetings next week, all eyes turn to the Chicago Cubs - a team with a short-term contention window and some serious decisions to make. This is the marquee moment of the offseason, where front offices gather, trade talks heat up, and rosters start to take real shape. For the Cubs, who made waves at last year’s Meetings by laying the groundwork for their deal to acquire Kyle Tucker, the trade market once again looks like their preferred path forward.
Now, don’t expect Jed Hoyer and his front office to tip their hand early - they didn’t last year, and it wasn’t until the final days of the Meetings that the Tucker deal truly came into focus. But while it’s tough to pin down exactly who the Cubs will target, it’s a bit easier to look at who they might be willing to move - particularly from a farm system that could be leveraged to fill holes on the Major League roster.
Let’s break down a few names to watch as potential trade chips heading into the Winter Meetings:
Owen Caissie: Staying Put
Let’s start with who won’t be traded.
Owen Caissie is being penciled in as a key piece of the Cubs’ outfield next season - essentially, their internal answer to the void left by Tucker. Whether that’s the right call is up for debate, but short of the Cubs diving into the deep end of the free-agent pool for someone like Tucker (again), Cody Bellinger, or Kyle Schwarber, Caissie looks like a near-lock to remain in Chicago.
His power potential and left-handed bat are part of the long-term vision, and the front office seems committed to giving him a real shot.
**Kevin Alcantara: The Odd Man Out? **
With Caissie in the mix, the Cubs are already looking at four outfielders who could break camp with the big-league club in 2026. Add in the likelihood that they’ll seek out a right-handed veteran outfielder for some stability and experience, and suddenly Kevin Alcantara’s path to Wrigley gets a lot murkier.
Alcantara’s prospect stock has cooled a bit over the past year, but he still holds enough value to be a meaningful piece in a trade - especially if the Cubs are eyeing a cost-controlled starting pitcher. He’s athletic, toolsy, and still just 23, but with limited space in the outfield and other needs taking priority, he’s a name to watch on the move.
Moises Ballesteros: Bat-First, Fit Later
Moises Ballesteros is another young player who feels like a near-lock to make the Opening Day roster - not because of his glove, but because of his bat.
The 21-year-old has hit at every level, and there’s little doubt he’ll hit in the big leagues too. The question is: where?
The Cubs don’t seem entirely sold on Ballesteros as a full-time catcher, and if they don’t view him as a long-term backstop, he becomes a fascinating trade chip. His offensive upside makes him a valuable asset, and if the right deal for a top-end, controllable arm comes along, Ballesteros could be the centerpiece. It wouldn’t be an easy decision, but it might be the right one if it helps address a glaring need in the rotation.
Jaxon Wiggins: The Crown Jewel
Jaxon Wiggins is the name that’s going to come up in just about every conversation the Cubs have next week - and for good reason.
He’s the best pitching prospect in the system, with frontline stuff and a projected debut by the end of 2026. That kind of profile doesn’t get moved lightly, especially for a team that’s relatively thin on high-upside arms.
But every player has a price, and if the Cubs are seriously considering someone like Joe Ryan - a cost-controlled starter with two years of team control - then Wiggins could be the piece that gets it done. It’s a big swing, but it’s the kind of calculated risk that can pay off if the Cubs are truly trying to maximize this competitive window.
The Cubs aren’t in rebuild mode - far from it. They’re in that tricky middle ground where the farm system is strong enough to support a few aggressive moves, but every trade has to be carefully weighed against the long-term vision. The Winter Meetings will give us a clearer sense of how bold this front office is willing to be.
Whether it’s flipping prospects for pitching or holding firm with their young core, the Cubs are going to be one of the most interesting teams to watch next week. Buckle up - the hot stove is just getting started.