Feature photo of Owen Caissie by Rich Biesterfeld

I’m convinced that the longer I create these prospect rankings, the more difficult of a job it becomes. That is mostly thanks to the talent and depth of this system that has been assembled over the past few years of a rebuild that isn’t allowed to be labeled as a rebuild.

Regardless, I’ve made my list 40 names deep here today. Part of that is because there are just so many dudes that deserve to have their name featured in a prospect list and it’s also partially because I had to draw a line somewhere.

With every prospect ranking, please don’t get caught up too much in who ranked 34 vs. 38. I’d listen to an argument the opposite way of how I have it listed here and in fact, you could probably make a realistic argument for every single player listed below to be higher AND lower than what I have them ranked. Regardless, here goes nothin’…

1. Brennen Davis | OF, Triple-A

Am I being stubborn when PCA might deserve this slot? Potentially. But I’ve argued that Davis deserves to be the Cubs #1 prospect on Opening Day 2023 and I’m standing by that. Don’t get distracted by this year, Davis is still The Truth.

2. Pete Crow-Armstrong | OF, High-A

He’s got the high floor secured with his Gold Glove-caliber defense in center field and his speed and aggressiveness on the base paths. But the ceiling comes in the fact that he put up offensive numbers way closer to Matt Mervis than you’d expect. That’s why he was my Hitter of the Year in the system this year.

3. Kevin Alcántara | OF, Single-A

The highest upside in the system. We’re talking legit Top 15 in baseball type upside. I’m not sure Aaron Judge would have cracked 50 home runs this year in Myrtle Beach’s ballpark and Alcántara somehow swatted 15 as a teenager.

4. Jordan Wicks | LHP, Double-A

I’ve gone back and watched more Wicks starts from this past year and I’m even more convinced than I already was that he is the best pitching prospect in the system. Both his changeup and slider are legit putaway pitches and the heat is a little sneaky, too.

5. Owen Caissie | OF, High-A

Let him continue to mature as a hitter, hit the ball in the air more to let that power play, and hunt and turn on a few more mistake pitches and he becomes a feared hitter.

6. Cade Horton | RHP, Unassigned

There’s not a pitcher in the system that resembles Horton in the way he works. The fastball/slider combo might just be lethal for High-A hitters to begin next year’s campaign.

7. Cristian Hernández | SS, Complex

Some people might look at this ranking and think I’m way down on on Hernández given his pedestrian debut stateside. You shouldn’t. Instead, you should be really impressed by the first six names on this list.

8. Hayden Wesneski | RHP, MLB

I still worry a bit about the fastball but there’s no denying that Wesnasty’s slider is one of the best in the entire sport. That alone warrants this top ten placement.

9. Ben Brown | RHP, Double-A

His fastball is in the high-90s and he was just added to the 40-man roster yesterday. A slurve, like the one Brown features, can be a real tricky pitch to master. There are few really good ones, but the ones that are truly plus offerings are devastating on hitters. His might be there.

10. James Triantos | 3B, Single-A

I can’t reiterate enough that Triantos did every single thing we wanted him to do in full season ball this year. Next up: elevating (without making a very clear effort to do so) outside the brutal hitting confines in Pelican Ballpark.

11. Daniel Palencia | RHP, High-A

Of course there’s reliever risk, but I’ll continue to bang the drum that it should mean something that he can hold velo deep into pitch counts. He’s arguably the nastiest pitcher in the org and he’s ranked down here at 11. It’s comical.

12. Matt Mervis | 1B, Triple-A

I’m sure I’ll catch some heat for this but I truly feel like placing a first base prospect this high in a system that’s this good is remarkable. He’s gotta hit. And I expect him to continue to do so.

13. DJ Herz | LHP, Double-A

This pains me a bit because I’ve had to come back to earth on DJ but I’m really hoping he proves me wrong. More reliever risk that I had previously wished to admit and the command will need to come around.

14. Alexander Canario | OF, Triple-A

Both the ankle and shoulder injuries scare me a bit, to be completely honest. he probably fell nearly ten slots on this list because of them. Athleticism and explosiveness are key in his electric profile so I’m hoping for a proper and patient recovery.

15. Porter Hodge | RHP, High-A

I really tried to sneak Hodge up even higher here. It’s a top 5 slider in the org and his fastball and changeup have flashes of brilliance as well. This ranking is too low and I’ll be kicking myself when next season rolls around.

16. Kevin Made | SS, High-A

For a guy who has seen some pretty extreme ups and downs on the field, I’ve actually felt pretty consistent in how I view him as a prospect. Another run in South Bend will do him wonders.

17. Drew Gray | LHP, Complex

There seems to be plenty of optimism coming from Drew himself that there could be some increased velo with the heat and we already know spin rates are impressive here. I can’t wait to see a healthy Drew Gray in 2023.

18. Moises Ballesteros | Catcher, Single-A

I’m ready to declare Ballesteros as the new prettiest swing in the system. He is truly a pure hitter and has some serious pop in his bat. Is he a catcher long-term? His arm says yes, at least.

19. Caleb Kilian | RHP, MLB

I simply don’t know what to make of a season of command being his extreme strength followed by a season where there was little to no command every fifth day. What I do know is swinging strike rate is one of the worst in the entire system and that isn’t gonna get it done in the bigs.

20. Jordan Nwogu | OF, High-A

For posting the fourth best hitter in the system this year, I seem to have Nwogu awfully low. He improved in quite literally every offensive stat and metric you can imagine from 2021 to 2022 and I still don’t hate him defensively in the outfield.

21. Ryan Jensen | RHP, Double-A

I’ve consistently been the high man on Jensen over the past couple seasons and I’ll admit that I was prepared to come down off that for this prospect list. But then I remembered how well he took to coaching, how deliberate the Cubs were with their changes to his delivery, and their addition of him to the 40-man. So here we are.

22. Luis Devers | RHP, High-A

I love being able to comfortably rank the Cubs MiLB pitcher of the year as the 22nd best prospect in the system.

23. Ed Howard | SS, High-A

Returning from a gruesome injury like the one Silk suffered is not easy. I’m worried about what he looks like in his game action but he gets a little placeholder here for now.

24. Luke Little | LHP, High-A

He essentially had the same season Brailyn Marquez had in 2019 that caused Cubs fans to lose their ever-loving minds for 3 straight years.

25. Chase Strumpf | 2B/3B, Double-A

If you produce at the plate, you produce at the plate. I think the strikeouts can be cut down to a reasonable level while maintaining his new-found pop. Worth noting his defense was GREATLY improved this year.

26. Christopher Paciolla | SS, Complex

A high school draft pick to dream on. Triantos vibes? Verdugo vibes? I can’t wait to see his athleticism in action.

27. Yohendrick Pinango | OF, High-A

I’ll admit I was probably too high on Pinango before. The hit tool and bat control is next-level but I worry about him falling into the Billy McKinney trap of being too “regular” at the plate as he attempts to tap into power.

28. Jackson Ferris | LHP, Complex

Any innings in Myrtle next year would make me both surprised and pleased. But there’s a reason why he had first round grades during this year’s draft.

29. Jeremiah Estrada | RHP, MLB

The only thing keeping Estrada this low is that he’s a relief-only prospect. He can only bring so much value individually and if a couple things don’t go perfectly, he’s a middle reliever. But I mean it when I say I think he’s the future closer of the Chicago Cubs.

30. Kohl Franklin | RHP, High-A

I was happy for a healthy season from Kohl and want to acknowledge he was extremely unlucky. Add a slider, become more consistent with his delivery, rinse, repeat.

31. Reggie Preciado | IF, Single-A

Just a crappy year. Looked severely overmatched at the plate, went down with an injury, and still looked fairly uncomfortable in his return. I still have high hopes for Preciado, I’ve just tempered by expectations.

32. Miguel Amaya | Catcher, Double-A

Talk about a guy that simply can’t catch a break. I’m struggling with valuing catchers accurately these days but add in a prospect with this injury history and it’s nearly an impossible task.

33. Zac Leigh | RHP, Double-A

If Estrada is the future closer, then Leigh is the future 8th inning guy. Gross slider. Gross fastball. Gross.

34. Luis Verdugo | 3B, High-A

Verdugo has turned himself into a really decent hitter and a damn good defensive third baseman. I wanna see him continue to get stronger so he can hit for even more power like you would see from an ideal third base prospect.

35. Adan Sanchez | Catcher, DSL

A top international signing that tore it up in the Dominican Summer League is always a good thing. I’m preparing myself for his fast rise up this list over the next two years.

36. Nazier Mulé | RHP, Complex

Man, I just don’t know where to put this guy, honestly. Is he a two-way player or just a pitcher? I’m not sure but he’s kind of a freak. I’m keeping him down this low until I know more. Think of it as a placeholder.

37. Pedro Ramirez | 2B, Single-A

I know Pedro has a great hit tool but I’m gonna need more from a small second baseman, to be blunt. He’s exciting and he’s produced up until now, though.

38. Riley Thompson | RHP, Double-A

I’m still a huge Riley Thompson believer. Assuming he makes it through the Rule 5 Draft still a member of the Cubs organization (I don’t think that’s necessarily a given), he has a legit shot to serve as Major League depth in either the rotation or the bullpen.

39. Parker Chavers | OF, Single-A

If you watch enough prospect action, you latch onto a few player for whatever reason. It didn’t take me long of watching Chavers in college and his short time with the Birds to realize there’s just something about the way he plays the game of baseball that will allow him to rise through the system.

40. Yonathan Perlaza | OF, Double-A

We’ve reached the end and I think it’s appropriate that Perlaza gets the feature here at #40. I’m not exactly sure how his profile plays in Triple-A and the Majors but I’ll hand it to him he has just continue to improve over the years. The pop is now officially legit and he’ll serve as important MLB depth beginning next year. All of this is assuming his reported minor league successor contract is in fact in place…

Be sure to check out Todd Johnson’s list from yesterday, stick around for Greg Zumach’s list tomorrow, and our NSB collective rankings on Friday!