The 2025 MLB trade deadline is on July 31. That leaves teams with a couple of weeks to decide whether they will sell at the deadline to replenish their farm systems with prospects, or buy to help increase their odds of winning the World Series.
The Chicago Cubs can be considered buyers at the deadline, as they sit in first place in the NL Central after a great start to the season. Plenty of that can be attributed to their lineup, highlighted by Pete Crow-Armstrong, Kyle Tucker, Seiya Suzuki, and Kyle Busch, and their stellar bullpen. If there is one need the Cubs need to address, it's their starting rotation. Losing Justin Steele early on in the season made it an early need for the Cubs, especially if they plan on making it out of the National League in the postseason.
Jim Bowden of The Athletic answered questions from fans regarding the MLB trade deadline. One fan asked if the Cubs would be willing to trade away top prospects Owen Caissie or Kevin Alcantara, both of whom are outfielders, even though Tucker is a free agent after this season and Suzuki and Ian Happ are under contract for just one more season. Bowden says the Cubs will not hesitate when it comes to making a trade to help them win now.
"I get the impression the Cubs are “all-in” to win this year and will trade Caissie or Alcántara if that lands them the right pitcher(s). Caissie’s name in particular has come up a lot in my conversations and texts with front office execs in both leagues."
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Cubs open to trading top outfield prospects at deadline, even with murky future
There may be no better chance for the Cubs to go back to the World Series than this season. The thing is, as the fan who asked Bowden the question said, their future in the outfield does look murky.
The Cubs made the gigantic splash before the start of the season by acquiring Tucker from the Houston Astros. Tucker was made available because he was an impending free agent after this upcoming season. So, the Cubs sent over infielder Isaac Paredes, right-handed pitcher Hayden Wesneski, and third base prospect Cam Smith for essentially one year of Tucker. The hope is that the Cubs can convince him to sign long-term, but it appears he's ready to test free agency this winter.
But then, after the 2026 season, Suzuki and Happ could both hit free agency as well. If the Cubs were to lose any combination of Tucker, Suzuki, and Happ, after trading Caissie or Alcantara, the outfield depth looks bleak.
As for who the Cubs should be targeting by floating Caissie or Alcantara, Bowden mentions Mitch Keller of the Pittsburgh Pirates, Merrill Kelly and Zac Gallen of the Arizona Diamondbacks, and Sandy Alcantara and Edward Cabrera of the Miami Marlins as potential targets.
The Pirates may be sellers, but Keller will cost a lot considering he is on a relatively affordable contract through the 2028 season. The Diamondbacks, meanwhile, don't appear willing to trade away players and seem adamant on trying to make a postseason push. Then there's the Marlins, who are out of playoff contention and likely sellers.
The Cubs may call the outfield situation a "tomorrow problem," especially as they try to win another World Series title. But that is something to keep an eye on, especially if they trade away two of their top outfield prospects by the end of the month.