The obvious need that the Chicago Cubs will have at the MLB Trade Deadline is for a pitcher that they could, in theory, slot at the top of their starting rotation.
The Cubs' rotation has performed well in the early days of life without Justin Steele this season, but as the weather turns, chances are there will be some regression to the mean. Given that the Cubs have defined the 2025 season as a season where the expectation is that they will reach the postseason, not addressing the rotation would be an egregious oversight by Jed Hoyer's front office.
Assuming the Cubs will be in the market for an ace-caliber starting pitcher at the deadline, the prediction made by David Schoenfield in his latest piece for ESPN is a no-brainer. While detailing a player from each team who might be moved at the deadline, Schoenfield had outfielder prospect Kevin Alcantara listed as the trade candidate for the Cubs.
It would seem that Alcantara and fellow top prospect, Owen Caissie, are at the top of the list of theoretical Cubs' trade candidates. Given the makeup of the outfield at the Major League level with Ian Happ, Pete Crow-Armstrong, and Kyle Tucker, the Cubs may not have a path to consistent playing time for either Alcantara or Caissie. Tucker is the outlier, but assuming the Cubs will put every effort forward in signing him for the long term, the two outfield prospects likely will be popular names in trade talks this season.
After a slow start to the season, Alcantara is beginning to find his form with Triple-A Iowa. Entering play on Tuesday, Alcantara has a slash line of .276/.368/.414/107wRC+ through 68 plate appearances with the Iowa Cubs. Moving Alcantara may seem like a steep price for the Cubs, but it would be one the team would be comfortable making if they knew Tucker would be with the team for the next decade.
Beyond Alcantara, it wouldn't be a complete surprise if one of Jordan Wicks or Javier Assad is moved by the team. Not due to the Cubs shopping them, but the likelihood of a team wanting a cost-controlled starting pitcher if they are moving one of their top-of-the-rotation pitchers to the Cubs.