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.

Keep: IF Matt Shaw

Matt Shaw was already a keeper for the Cubs, but his stay in Chicago became even more permanent after the team missed out on third baseman Alex Bregman. Shaw has been preparing to play third base for two straight offseasons and is now poised to step into the starting role for the Major League squad in 2025.

Shaw's abilities have been very convincing since he was drafted in the first round in 2023. He has stormed through the minor league system, hitting for both power and average at all levels with solid defense and great speed. He is the no. 1 prospect in the team's system and is currently at the top of the third base depth chart as well.

The Cubs need him and he seems to have the attitude and work ethic to excel in the Majors. It remains to be seen if he can live up to the hype, but his track record is impressive and his projections point to a great rookie season, with some considering him a candidate for the National League Rookie of the Year award.

Trade: Cade Horton

This is controversial, but I think there is a case to be made for trading Cade Horton, who is the highest-ranked pitching prospect in the Cubs' system. But just like Alcantara, this has nothing to do with Horton's talent level. When healthy, Horton has flashed some really amazing stuff on the mound, with a mid-to-upper 90s mph fastball and a wipeout slider that generated a 50% swing-and-miss rate last year. If he can develop his secondary pitches and stay healthy, Horton has ace potential in the future.

But the problem is that Horton's career has been riddled with injuries, and he has pitched just 176.1 innings over his last four seasons between the minor leagues and college. Yet he is still ranked extremely high (no. 52 in MiLB) due to his immense potential. This evaluation is precisely why Horton would be a great guy to trade as he can be a main piece to bring a high-level starter or hitter to the major league squad.

The positional need is also a variable here. The Cubs have a lot of starting pitching depth in the system, including Jordan Wicks, Ben Brown, and Brandon Birdsell among others. The Cubs don't have room for all of them in future iterations of their rotation, so the Cubs need to part ways with someone at some point. Horton may have the highest ceiling out of all those names, but he also comes with the most risk so trading him while his stock is high could be the only shot the Cubs have to maximize his value.

I could be totally wrong, and Horton may be the next version of Dylan Cease, who the Cubs traded at a similar point in his minor league career only to watch him blossom into a Cy Young-caliber pitcher. I certainly would not be mad if the Cubs kept Horton

Keep: IF/OF James Triantos

James Triantos is a second baseman who has drawn a lot of comparisons to Nico Hoerner. Both possess plus speed, low strikeout percentages, and elite contact-hitting abilities. In 115 games in Double-A and Triple-A last season, Triantos swiped 47 bases, struck out just 11.1% of the time, and posted a 123 wRC+ while slashing .300/.346/.427.

The 22-year-old does not hit for power and has been described as fringy on defense, but the latter can be improved in time, especially if he is locked into second base long-term. The Cubs have been giving Triantos looks in the outfield, but it seems like his future remains at second base.

With the Cubs looking to save money wherever they can these days, they may want to hold Triantos in their back pocket until Nico Hoerner reaches free agency after the 2026 season. And honestly, it could be a smart play. They are very similar players, and the free agent market for second basemen is fairly light over the next couple offseasons, with Hoerner himself leading the 2027 free agent class. From a roster standpoint, it makes a lot of sense to keep Triantos long-term and try to develop his defensive skills until the team is ready to part ways with Hoerner.

Trade: C/1B Moises Ballesteros

For being ranked the 69th best prospect in baseball, Moises Ballesteros basically brings one thing to the table. And it's his ability to hit. Evaluators from within and outside the Cubs organization rave about Ballesteros' advanced hitting skills from the left side of the plate, but not much else.

He is very slow on the base paths and doesn't have a long-term defensive position. Many scouts and reporters question whether Ballesteros can be a Major League catcher with his abilities, or lack thereof. His 2025 scouting report points to slow footwork and transfer speed that led to baserunners swiping 88% of the time on him last season, with seven errors and 13 passed balls.

The 21-year-old is far from a finished product and he can definitely improve some of his skills. He has reportedly lost a lot of weight in an effort to improve his quickness behind the dish. But it seems like a stretch that Ballesteros will work out as a big-league catcher, and it feels like the Cubs know that. They tried to trade for Logan O'Hoppe at the 2024 trade deadline, a young-controllable catcher with hitting upside.

The only other position Ballesteros makes sense at is first base, which will be covered by Michael Busch for the foreseeable future. And this is also seen as questionable considering Ballesteros is just 5'8, and it's a sort of an unofficial prerequisite that catchers are at least over six feet tall. It really feels like the young prospect is destined to be a full-time designated hitter and there's honestly nothing wrong with that as long as he and the Cubs are willing to wait a long time. If a team like San Diego or Toronto thinks highly of him, I would definitely not be mad if Ballesteros was part of a trade package. I think it's hard to see a fit for him with the Cubs in the future and he may thrive somewhere else.