The Chicago Cubs are, right now, doing so well this year that it’s a big temptation to not event think about further down the road.
But, as all baseball people know, hot streaks don’t last forever. Sooner or later everything comes back down to earth and reality rules.
The Cubs’ reality is that they lost their top-of-rotation ace, Justin Steele, and that, at some point in the not too distant future, that loss will be felt. Fill-in Colin Rea has been excellent so far, but it’s not reasonable to believe, given his career stats, that he will continue to be an all-star quality starter. And even if Rea DID keep up his early season pace, there’s still the matter of Chicago adding a viable and consistent fifth starter to the rotation.
The Chicago Cubs Will Have To Make A Trade

So, the Cubs will definitely have to make a deal for a quality starting pitcher before the trade deadline if they remain serious playoff contenders.
The main question, though, is who they will target. The secondary question is who they will have to give up to get their target.
Possible Cubs trade targets include Sandy Alcantara of the Miami Marlins, Luis Castillo of the Seattle Mariners, Pablo Lopez and Joe Ryan of the Minnesota Twins, Tyler Anderson of the Los Angeles Angels, and Martin Perez of the Chicago White Sox.
The answer to the “who will they trade away” question is a little trickier.
Who Will The Cubs Have To Trade Away?

Whichever team answers the trade call will, for sure, want one of the Cubs’ top prospects. Cade Horton, Owen Caissie, Kevin Alcantara, or Moises Ballesteros will have to be moved. They’d also probably want a young majors-ready player.
Jordan Campbell of Cubbies Crib brings up two names likely to be included in any big deal– outfielder Kevin Alcantara and pitcher Jordan Wicks.
Alcantara is the easiest choice since he’s an outfielder who, at the moment, has no starting slot open for him at the major league level. With Pete Crow-Armstrong in center, Ian Happ in left, and the team hoping to extend right fielder Kyle Tucker, there’s nowhere for Alcantara to go. The same goes for Caissie, although it’s more feasible that Caissie might grab Happ’s corner outfield spot at some point.
Whatever the case, an outfield prospect will probably be dealt.
In terms of pitcher trade fodder, Wicks makes the most sense given his past spots of major league success and his current status as an off-the-26-man-roster asset.
Campbell makes the case that the Cubs are already playing him as if he’s on the trade market:
“Look no further than how Wicks has been handled to open the 2025 season. Wicks opened the season with the Triple-A Iowa and, despite looking like a clear candidate to replace Justin Steele in the Cubs’ Major League rotation, he was only called upon when the Cubs were in need of a fresh arm in the bullpen. Wicks was quickly sent back down to Iowa after giving up 5 runs (3 earned) on 6 hits across his two appearances out of the Cubs’ bullpen. To Wicks’ credit, the way he was used didn’t quite match his profile.”
A Possible Package Idea

Another player could be packaged with Alcantara/Caissie and Wicks in a deal structured similarly to the one that brought Kyle Tucker over from the Houston Astros.
Matt Cozzi of the Locked on Cubs podcast talked about a possible trade package for a starting pitcher during a February episode of his show:
“They have their own trade…as a possible format…It would be a combo platter here of three players. One is a major league starting position player or pitcher. One’s a top prospect. And then a third piece who’s in limbo or blocked with the Cubs, but offers major league value of some sort on day one with the team. And that was the Astros trade.
So, here’s what it would be this time.
I think it would be either [Javier] Assad or [Jordan] Wicks because they immediately go into the rotation, either [Kevin] Alcantara or [Owen] Caissie, and a third player, someone of the ilk of Wesneski…”
The Cubs have the farm system depth to pull off such a big, headline-grabbing trade. For now, though, the focus has to be on winning and keeping themselves in a position where they will actually need some reinforcement for a playoff run.
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