3 prospects the Chicago Cubs should keep, and 3 they should trade

After a relatively productive offseason, the Chicago Cubs front office can still upgrade the roster by trading from its top-heavy farm system.

Although team President Jed Hoyer successfully revamped the bullpen and acquired a top bat in the game by trading for Kyle Tucker, there are still holes to be filled on the roster. Notably, the Cubs failed to meaningfully upgrade the starting rotation with a top-level pitcher. This goal can still be accomplished between now and the 2025 trade deadline and the Cubs have the prospects to do it.

While it's usually not advised to cling to prospects because many of them end up failing to grow into productive Major Leaguers, the Cubs have a handful of guys worth keeping. Here are the prospects that I think are worth keeping, and the ones I

Keep: Owen Caissie

Left-handed hitting sluggers are a tough commodity to come by in MLB, and the Cubs know this better than anyone. After trading former first baseman Anthony Rizzo and non-tendering outfielder Kyle Schwarber, the Cubs have struggled to field a power-hitting lefty in their lineup. Michael Busch and Kyle Tucker are in a good position to buck that trend in 2025, but Tucker will very likely depart in free agency after this season.

On paper, Owen Caissie would be the perfect guy to take Tucker's spot in right field for 2026 and beyond. At just 22 years old, Caissie has already established himself as one of the best power-hitting prospects in baseball with a career of .278/.383/.470 slash line in 406 minor league games. At the Triple-A level last year, Caissie showed he could hit for power with 51 extra-base hits, while also using good plate discipline to take 71 walks. His ability to balance aggression and patience could make him a dangerous hitter if he stays on his current trajectory.

Standing at 6'3, Caissie has also flashed average defensive abilities and a plus throwing arm, leading MLB dot com to profile him as a corner outfielder and ranking him 54th among all prospects heading into 2025. Since Caissie was also ranked No. 2 in the Cubs' system last year, it will be difficult to persuade teams to exclude him from trade packages. But the Cubs need to hold onto Caissie, as he is the best chance for the team to have a young slugging outfielder for years to come.

Trade: OF Kevin Alcantara

If the Cubs keep Caissie, Kevin Alcantara becomes much more expendable, but not because of a lack of talent. Alcantara is also 22 years old and currently ranks 90th on MLB Pipeline's top 100 list. While Alcantara's power hasn't shown up as much as Caissie's, he has more tools and athleticism. Alcantara features plus speed, defensive abilities, a solid throwing arm, and the ability to play center field as well as the corners.

Once Alcantara fills out his 6'6 frame and improves his plate discipline, he could blossom into a fierce Major League hitter. And the Cubs would be wise to cash in on that potential now and make him the center of a trade package. Caissie and Pete Crow-Armstrong would be able to handle center field and right field for the foreseeable future, while a replacement or extension for left fielder Ian Happ would have to be addressed before 2027.

The Cubs have enough outfielders to part with Alcantara, and he can be the main component in a package for a starting pitcher like Pablo Lopez or Luis Castillo. I would like to see Alcantara stay and hope that he would become a great asset for the major league roster, but the Cubs may have to strike a big trade in the near future and Alcantara is more expendable than Caissie in my mind.