Former MLB Exec Shares Cubs Stance About Prospects Ahead of MLB Trade Deadline

The Chicago Cubs are in a great spot, just a few weeks out from the 2025 MLB trade deadline.

They have been playing a great brand of baseball all season, currently sitting in first place in the National League Central with a 54-37 record. But, they are not in the clear yet, only 2.5 games ahead of the surprisingly strong Milwaukee Brewers.

The Cubs have been getting the job done behind one of the most prolific offenses in the sport, led by NL MVP candidates Pete Crow-Armstrong and Kyle Tucker.

More News: Cubs Exceeding Lofty Preseason Expectations With Stellar All-Around Production

Both are playing at an exceptionally high level, setting the tone that their teammates have followed suit on.

Seiya Suzuki, Michael Busch, Carson Kelly and Nico Hoerner are all putting together the most productive seasons of their respective careers, helping Chicago really take off.

However, if the Cubs want to remain atop the division and continue challenging for the best record in the NL, there is some work to do ahead of the trade deadline.

More News: Cubs May Be Forced Pay Premium to Acquire Rival's Pitcher at Trade Deadline

Chicago’s ownership has to allow the front office to aggressively pursue upgrades, especially on the mound.

The Cubs’ pitching staff has been solid, but their starting rotation is lacking front-end talent and depth in general, with Justin Steele suffering a season-ending injury.

It wouldn’t hurt to add an experienced arm to the backend of the bullpen either. Still, at least Craig Counsell is receiving excellent production from Daniel Palencia, Caleb Thielbar, Drew Pomeranz, Chris Flexen, and Brad Keller to make up for some of the struggles of Ryan Pressly and Porter Hodge.

To acquire the kind of talent that would help Chicago be in the same tier as the Los Angeles Dodgers, Detroit Tigers and Houston Astros when it comes to starting pitching, they need to be willing to give up something of value.

More News: Cubs Can Form Insane Bullpen by Reuniting With World Series Hero at Trade Deadline

Jim Bowden of The Athletic (subscription required) has heard it is something they would be willing to do for the right player.

“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,” the former MLB executive wrote.

There would be some risk involved in moving Owen Caissie or Kevin Alcantara, given the uncertainties of the team’s outfield in the future.

Tucker is set to be a free agent after this year. Ian Happ is going to hit the market after the 20206 campaign and Suzuki could as well.

More News: Cubs Slugger Listed as Snub From National League All-Star Team

Caissie and Alcantara could certainly be part of the contingency plans should veterans depart in free agency, creating a difficult balancing act for the front office to pull off.

Competing for a World Series is never guaranteed in the future, so no one would blame them for being aggressive this year.

With Tucker only guaranteed to be in the mix this year, going all-in would be the right move for the franchise.

For more Cubs news, head over to Cubs On SI.