Chicago Cubs Top Prospects: Midseason Top 30 Chicago Cubs Prospects (#10-6)

The Chicago Cubs have a solid minor league system that features legit star power, high ceiling/low floor guys, and high floor/low ceiling guys. The system isn’t top heavy, it’s deep and there are more than 30 guys that could have made this list, but these are the 30 guys that I believe are:

1. Most likely to make an impact on the major league squad
2. May be less likely to make the league, but if they do they have legit star power.

Earlier this week we looked at the 30th-21st best prospect as well as the 20th-11th best prospect in the system. Later this week we’ll look at the Top 5 prospects but until then, here is the 10th-best prospect in the Chicago Cubs minor league system. 

Number 10 

Owen Caissie OF 

Age: 21 Years Old

Level: Double-A Tennessee Smokies

Joined the organization via: Yu Darvish Trade with the San Diego Padres

2023 Stats: .271/.373/.500 15 HR, 18 2B, 6 SB 56 RBI, 47 R

Owen Caissie was acquired along with journeyman RHP Zach Davies, SS Reginald Preciado, OF Ismael Mena and SS Yeison Santana. Davies is out of the organization and none of the other players are above High-A right now. 

There were obviously monetary reasons that prompted the Darvish trade that outweighed the baseball side of things, but regardless of why the trade happened, if Caissie continues to hit the way he has this year then he could make that sting a little bit less.

He’s been moving alongside Pete Crow-Armstrong and the two look as though they could be making an impact at Wrigley Field sooner than later, but the thing that may stand in Caissie’s way is that he has an incredible 115 strikeouts this season. That isn’t a new development, either. Last season he had 124, but he also had nearly 100 more plate appearances to get to that number.

Pitching is obviously better the higher you go, but Caissie’s inability to control the strike-zone is the only thing preventing him from being higher on this list. He needs to get better at picking his spots on the basepaths as well considering he’s been caught stealing more often than he’s successfully taken the base (6-for-13), but that aggressive play style seems to be something that the Cubs are reinforcing rather than redirecting.

If he can manage to reduce the strikeouts, be more selective in his base-stealing and continue to put together the power production he has this season, then he becomes a legitimate contributor whether it’s in a corner outfield position or at DH.

Number 8

Moises Ballesteros

Age: 19 Years Old

Level: High-A South Bend Cubs

Joined the organization via: IFA Signing in 2021

2023 Stats: .274/.394/.457 8 HR, 12 2B, 5 SB, 32 RBI, 28 R

Moises Ballesteros was our choice for the best hitter of the first half at High-A South Bend. There’s a lot to like about him as a player but I’ll start simply by comparing him to Hernandez because they were signed in the same international class and are both just19 years old. 

Ballesteros plays the position on the field that takes the longest to develop and yet he has been promoted to High-A this season while Hernandez is still struggling in Low-A Myrtle Beach. Ballesteros has walked 52 times this season compared to just 45 strikeouts. Ballesteros has also not been caught stealing in his five attempts.

Since being promoted to High-A he’s walked 12 times and struck out 15 times. For his (albeit brief) career, he’s walked 114 times compared to 116 strikeouts. To have a hitter patient enough to draw that many walks but with strong enough bat-to-ball skills to not strike out a ton is exceedingly rare. It’s even more rare for that player to be a catcher and somehow even more rare still for that player to be a teenage catcher at High-A.

The Cubs are in a great position with catchers in their system. Miguel Amaya is hitting his stride and learning from two of the best defensive catchers going right now with Yan Gomes and Tucker Barnhart at the major league level. Pablo Aliendo is seemingly closer to the bigs than Ballesteros at Double-A and they just drafted a couple of guys that have intriguing tools at the plate if they can stick behind the dish. That being said, Ballesteros is the best out of all of them and it’s not close in my opinion. I can’t wait to see this kid over the next couple of years and eventually at Wrigley Field.

Number 7 

Jordan Wicks LHP

Age: 23 Years Old

Level: Triple-A Iowa Cubs

Joined the organization via: 1st Round Pick in 2021 MLB Draft

2023 Stats: 71.2 IP 3.89 ERA 82/25 K/BB

Jordan Wicks was our choice for the best pitcher of the first half at AA Tennessee. He’s never been as dominant with the strikeouts as some of the players you’ve already seen on the list or others you will see later on the list, but he’s also had much more control than a lot of those pitchers as well.

Wicks is striking out 10.3 batters per nine innings so far this season which is pretty close to his career averages. In the minors he’s averaged 10.8 and in college he averaged 10.2, so the 10.3 just goes to show his remarkable level of consistency. To go along with that consistency with the strikeouts he’s also been very consistent at keeping his BB/9 under three as well.

He’s struggled a bit since making the jump to Iowa, which was to be expected. He was exceptional at Double-A, with a 3.39 ERA over 58.1 innings and he kept his BB/9 at 2.9. That being said, since arriving in Iowa he’s seen that number creep to 4.1 which, if the season ended today, would mark the highest such mark of his young career. 

Similar to DJ Herz and some other pitchers earlier on our list, Wicks has never been deployed as anything other than a starter. That makes sense considering his stuff isn’t super overpowering and he’s the kind of pitcher that gets better as the game wears on, but it says something about the makeup that the Cubs believe he has. 

In an ideal world, Wicks isn’t someone we’re considering coming up this summer unless there are significant issues pitching-wise. Even with losses of Marcus Stroman or Drew Smyly at the deadline, there are at least two guys ahead of Wicks in the pecking order in Ben Brown and Hayden Wesneski. Still, don't rule out seeing the southpaw at Wrigley at some point in 2024.

Number 6 

Cade Horton RHP

Age: 21 Years Old

Level: High-A South Bend Cubs

Joined the organization via: 1st Round Pick in 2022 MLB Draft

2023 Stats: 53.2 IP 3.19 ERA 78 K/16 BB

If I’m being honest, on the initial list I made of the Cubs top-30 prospects, I had Cade Horton higher than this. I was very pessimistic about the pick at the time in the 2022 MLB Draft, but I’ve been put in my place every single time he’s taken the mound this season. 

Let’s get the low-hanging fruit out of the way early. He put up sterling numbers against very young and inexperienced competition to start the year at Myrtle Beach. That being said, what I liked about Wicks is true for Horton as well, just to a greater extent. This season, Horton has struck out more than 13 batters per nine innings and limited the walks to less than three per nine innings.

Jed Hoyer and the Cubs recognized a lack of power hitting and power pitching and seemingly didn’t do much to take care of either of those problems at the major league level. However, with their draft picks and trade targets over the last two seasons they’ve done everything they can to homegrow that talent and Horton appears to be one of the fruits of that labor. 

He could be at Tennessee to start next season and if he does to Double-A hitters what Brown did to start this season then he could easily find himself in Iowa before the season is over with the possibility of making the big league Opening Day roster in 2025.