Kevin Alcantara, other Cubs prospects who could be traded during the Winter Meetings

The Winter Meetings are next week, and that is the tentpole event of Major League Baseball's offseason. It was at the Winter Meetings last year when the Chicago Cubs set the parameters for their trade for Kyle Tucker, and the trade market will likely be the preferred direction the team travels once again at baseball's gathering of all the important people.

Even a week before the event, it's hard to say specifically who Jed Hoyer and Co. will target. It wasn't until the end of last year's Winter Meetings that it became clear that not only were the Houston Astros going to trade Tucker, but that the Cubs were the most aggressive suitor.

It's a far easier game to point to the players whom the Cubs might be willing to trade at the Winter Meetings. A team in the middle of what appears to be a short-term contention window, they could look to trade from the top of their farm system to address the needs on their Major League roster.

Cubs prospects who could be traded during the Winter Meetings

One prospect who likely won't be traded is Owen Caissie. As flawed as their logic may be, the Cubs are pointing to Caissie as the primary replacement for Tucker in their starting lineup next season. Short of the Cubs being willing to engage Tucker, Cody Bellinger, or Kyle Schwarber on the free-agent market, Caissie feels like a near lock to remain with the team this offseason.

Kevin Alcantara

With Caissie in the fold, the Cubs already have four outfielders earmarked for the Major League roster to open the 2026 season. Add in the impression that the Cubs may be looking for a right-handed hitting veteran outfielder to offer some insurance for Caissie, and Kevin Alcantara suddenly appears to be out of the picture. His prospect shine has worn off, but the Cubs could still look to move him as one of the main pieces in a trade for a cost-controlled starting pitcher.

Moises Ballesteros

Like Caissie, Moises Ballesteros feels like a lock to make the Cubs' Opening Day roster. However, one reason why the Cubs may entertain the idea of making him the key prospect in a trade this offseason is the fact that he may not have a position. Ballesteros' bat will make him a clear option to be in any team's starting lineup, but Chicago doesn't appear enamored with the idea that he can be an everyday catcher. If presented with the right trade for a cost-controlled ace, the Cubs may be willing to include Ballesteros in the deal.

Jaxon Wiggins

As was the case at the MLB trade deadline, teams are going to ask about Jaxon Wiggins at the Winter Meetings. Wiggins is the best pitcher in the Cubs' system, with many believing he will not only emerge as an ace at the Major League level but also make his debut by the end of 2026. The Cubs are thin when it comes to pitching prospects, so they likely will want to hold onto Wiggins, but in a deal for Joe Ryan, under control for two more seasons, perhaps they are willing to make an exception.