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 9 

Cristian Hernandez SS

Age: 19 Years Old

Level: Class-A Myrtle Beach Pelicans

Joined the organization via: IFA Signing in 2021

2023 Stats: .221/.291/.298 4 HR, 4 2B, 2 3B, 13 SB, 27 RBI, 29 R

It’s odd to say that patience is running thin for a 19-year-old, but that’s the situation we find ourselves in with Cristian Hernandez. Going into the 2022 season he was ranked as a top-100 prospect in baseball after a season in the Dominican Summer League that saw him hit .285/.398/.424 with five homers and 21 stolen bases. 

Unfortunately, in the following season he saw his numbers falter in Rookie ball as he went .261/.320/.357 with three homers and just six stolen bases in nine attempts. That didn’t prevent him from being promoted to Low-A Myrtle Beach this season though, with the hopes that he’d put it back together and start to earn the $3 million dollar signing bonus he earned in January 2021. 

He’s been considerably worse this season than ever before. He’s played in nearly twice as many games as either of the previous seasons, and neither his OBP nor his slugging percentage are over .300. He has 10 total extra-base hits in 285 plate appearances and he’s striking out nearly four times as often as he’s walking.

That being said, the ceiling is incredibly high. MLB.com doesn’t have a single tool as less than a 50 future grade. They point out that his physical comparisons at the time of signing compared to Alex Rodriguez and Manny Machado. 

There are so many opportunities for things to go wrong here. He’s already made his money, he’s never had a truly exceptional season stateside, he’s been aggressively bad this season, etc. But there are also so many chances for this to go right. He’s got the look, he’s got the tools, he’s just got to put it all together and he has plenty of time to do that because he’s still younger than just about every pick the Cubs made in the 2023 MLB Draft. 

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.