After trading Moises Ballesteros and Jefferson Rojas at the trade deadline, Jed Hoyer managed to keep the overwhelming majority of his prospect base, while also addressing all of the Chicago Cubs' needs at the big-league level.
But given that not only Kevin Gausman and Clay Holmes are free agents at years end, but will be joined by Colin Rea, Shota Imanaga and Matthew Boyd, the Cubs are going to be scouring the market for pitching heading into 2027 as they look to re-shape a rotation around Edward Cabrera, Justin Steele and, hopefully, Ben Brown and Cade Horton.
Kevin Alcantara, who has put together another strong year at Triple-A Iowa (albeit not without the lingering swing-and-miss concerns still being a thing), feels like a strong trade candidate this winter. If you look at it a different way, though, Seiya Suzuki and Ian Happ also hit free agency, so Alcantara might get some runway in a corner outfield spot. But moving past Alcantara, one name seems likely to move this winter: James Triantos.
Pedro Ramirez' breakout season has major impact on James Triantos
Triantos does a little bit of everything defensively and, despite being on the 26-man heading into the weekend, has just four at-bats since joining the team back on July 25. Pedro Ramirez is clearly Craig Counsell's favorite go-to bench piece and there's a good deal of overlap between him and Triantos, likely making the latter available this winter.
A former top-100 prospect, Triantos made his name in the Cubs' system with his elite bat-to-ball skills, drawing some comps to current Chicago second baseman Nico Hoerner. The only problem is he's far from the elite defender that Hoerner is and with the utility role filled by Ramirez, it appears that Triantos may be running into a wall coming off the 2026 season.
He's already got two full seasons at Triple-A under his belt (and part of a third), so running him back to Des Moines again in 2027 doesn't seem like it does anyone much good. But if you can package him in an offseason trade that helps address the rotation, there's not really a negative impact on the big-league product. If I were picking one prospect that could be moved (other than Alcantara), my pick right now is Triantos.
