The Chicago Cubs headed into the offseason looking to upgrade the starting rotation, but outside of a two-year contract for Matthew Boyd, they have not really done that in a meaningful way thus far.
Seen as a serious suitor for Jesús Luzardo of the Miami Marlins before they instead dealt him to the Philadelphia Phillies, reliable reporting has placed the Cubs at the center of the market for a starter. But to this point, nothing has materialized.
The Luzardo rumors seemed to have serious steam at the outset, but for whatever reason, Chicago’s name cooled off towards the end of the sweepstakes and he instead ends up with the Phillies.
Perhaps there’s still someone out there who would fit the bill in terms of what the Cubs are looking for to add to the rotation and strengthen what already is one of the better units in the league.
In a proposed hypothetial deal, Zachary D. Rymer of Bleacher Report said Chicago could acquire Seattle Mariners three-time All-Star Luis Castillo in exchange for one of their best prospects in outfielder Owen Caissie.
“It’s in the Mariners’ interest that the Cubs’ farm system is loaded,” he wrote. “So much so, in fact, that it would be worth paying down some of Castillo’s remaining money to get at one of the better players within said system.”
With Caissie on the verge of being big league ready and without a doubt the best power hitter in the Cubs’ system, dealing him away would sting.
But Chicago already has spots occupied in the outfield between Ian Happ along with a desire to keep Seiya Suzuki, extend Kyle Tucker, and have defensive standout Pete Crow-Armstrong remain involved. There may not be room yet for Caissie, who is absolutely raking at the Triple-A level and should be ready for MLB pitching this season.
The downside with Castillo is of course the money he’s owed, with $25 million remaining in each of the next three seasons with a vesting option in 2028. In Rymer’s proposal however, the Mariners take on at least a portion of that money and make it an easier sell for Chicago to justify parting with an elite prospect in exchange for an All-Star pitcher under affordable team control for the forseeable future.
A deal like this really comes down to what the Cubs believe Caissie is capable of being. If they think he’s a future superstar, getting just Castillo in return doesn’t feel like enough.
Undeniably however, a pitcher like Castillo would bring the Chicago rotation to the next level and make an already good staff one of the best in baseball.