Outfield Prospect Could Be Centerpiece of Trade Talks for Chicago Cubs This Winter

Will the Chicago Cubs enterain offers on their talented outfield prospect?

Iowa Cubs' Owen Caissie walks in the outfield during a game against the Toledo Mud Hens at Principal Park on Tuesday, April 2, 2024, in Des Moines. / Lily Smith/The Register / USA TODAY NETWORK

The Chicago Cubs entered the winter hoping to make some improvements to a team that was good, but not great in 2024. 

Despite finishing over .500 last year, the Cubs were never really in the playoff picture in the stretch run of the season.

There were a lot of good teams in the National League, and Chicago knows they will have to make some improvements if they are going to compete next year. 

Coming into the offseason, the Cubs likely would have been in the mix for some of the top free agents available, however, due to Cody Bellinger opting in for 2025 instead of seeking a long-term deal in free agency, Chicago might be a little handicapped in terms of how much they will be willing to spend. 

If free agency isn’t going to be the way that the Cubs improve, they will have to explore the trade market.

Fortunately, Chicago has a very deep farm system, and with not a lot of room in the Majors to play, trading a prospect or two seems likely. 

Recently, Joel Reuter of Bleacher Report spoke about Cubs prospect Owen Caissie as a potential centerpiece in trades this offseason. 

“Cassie, 22, is one of the most MLB-ready prospects in the minors right now following a standout full season at Triple-A, but with Ian Happ, Cody Bellinger, Seiya Suzuki and Pete Crow-Armstrong all vying for playing time in the Cubs outfield, it's unclear how he fits in 2025. Flipping him for pitching help could be the best way to maximize their current talent.”

With a logjam of talent in the outfield, moving Caissie is certainly a possibility for Chicago this offseason.

Ideally for the Cubs, Bellinger would have gone into free agency, freeing up time in the outfield for a player like Caissie to come up. Also, that would have allowed them to pursue either a middle of the order bat, or some more pitching. 

However, with free agency possibly not being the way they make improvements, trading some of their young prospects could result in Chicago bringing back some excellent talent. 

The young outfielder would be wasted going back to the minors in 2025, as while it might not be an ideal situation, the Cubs do have other needs on the roster.

If they could trade the talented young prospect for some pitching help, it would go a long way toward helping them compete and take control of the National League Central. 

As the winter meetings kick off soon, Caissie will be a name worth watching for a Chicago team that could be aggressive on the trade market.