Five Chicago Cubs Top Prospects to Watch at MLB Trade Deadline

The Chicago Cubs have the prospects it needs to get just about any deal done as the MLB trade deadline approaches.

Most analysts believe the Cubs have one of the best farm systems in baseball and, regularly, at least four or five players are ranked in baseball’s Top 100 prospects. That’s the sort of talent that can help a Major League team, whether it be in the Windy City or somewhere else.

Chicago doesn’t want to sacrifice its future. But the Cubs are in position to contend for a World Series and those chances don’t come along often. Sometimes, dealing a prospect or two is the price of doing business.

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Here are five prospects the Cubs could include in trades to make the team better for a playoff push. For the purposes of this piece, only prospects with no MLB service time were considered.

OF Owen Caissie

MLB Pipeline considers Caissie the franchise’s No. 1 prospect that hasn’t played in the Majors yet.

Caissie is ready for a call-up, but he’s blocked by an incredible group of outfielders in Wrigley Field. The logjam only gets worse if the Cubs manage to sign Kyle Tucker to a long-term extension.

If the Cubs are seeking a high tier starting pitcher to help Shota Imanaga, Caissie is likely to be part of the asking price. Depending upon how badly Chicago wants to win, the young star may be in a new organization come August.

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INF/OF James Triantos

The bloom is off the rose just a bit for Triantos, who played in the MLB Futures Game last year. But he’s at Triple-A, just 22 years old and can play second base and outfield. He’s also the Cubs’ No. 5 prospect.

If the Cubs go after a Sandy Alcantara or a pitcher of his ilk, Triantos is going to be on the table as part of the deal.

P Jaxon Wiggins

The former Arkansas star is an imposing 6-foot-6. He had Tommy John surgery in college, and he’s quickly emerged as a Top 10 prospect in the Cubs’ organization. He’s now at Double-A and could be ready as soon as next year.

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He has a fastball that remains at high velocity deep into games. He could end up a starter or a reliever in the Majors. His arm talent will intrigue trade partners.

SS Ty Southisene

He has a ton of potential but is years away from a Major League call-up after he was taken in the fourth round of last year’s draft out of the prep ranks.

If the Cubs are in the market for a top starting pitcher, a player like Southisene — who has potential but needs time to develop — becomes a throw-in for a multi-player deal.

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INF/OF Jonathan Long

Drafted in 2023, he’s already at Triple-A Iowa. He has power, quick hands and can play both corner infield positions, as well as the outfield. Scouts aren’t wild about his fielding, so he may end up being a full-time DH at some point.

But he’s just 23 years old and the fact that he’s already in position to help an MLB team as soon as next year will make him an enticing trade piece.

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