Updating My Prospect List Ahead of the MLB Trade Deadline

Photo of Owen Caissie by Rich Biesterfeld

This feels weird.

It’s actually the first time I’ve penned an article since our “Goodbye & Thank You” piece over at North Side Bound this winter. And while I’m definitely out of practice on the writing front as I’ve focused my energy on the podcasting side of things, two facts lead me back here today:

  1. I’m as tuned in with the Cubs system right now as I ever have been. Box scores every night, a few full games per week, several starting pitcher speed-runs per week, countless statistical deep dives. You name it, I’m nerding out about it.
  2. I have posted a prospect list both in the offseason and midseason somewhere online for nearly a decade now, so I wasn’t about to stop now.

This edition includes 30 prospects with notes on each one. My rankings include only players that have made their full-season debut. So much of my evaluations come from watching the way they move on the diamond and from detailed public data, often at a pitch-by-pitch level of specificity, neither of which I can get from guys playing in either the Arizona Complex League or Dominican Summer League. Also excluded from this group are this year’s draft picks (because they haven’t debuted in full-season ball), but I give some ideas of where I’d rank them at the very end of this piece.

Finally, this system is no longer what it once was. Sure, there are some usual names up top and players that are ranked in Top 100s. But once you get down to the teens in my rankings, there is so little margin between the prospects and it really and truly becomes a “pick your favorite” scenario. I’ve picked mine below, and hope you don’t get mad I didn’t include your fav a few slots higher. I say this because I feel fairly passionate about the tiers I’ve laid out below. Once you get into Tiers 3, 4, and beyond, it’s a desperate search for very fine and specific physical qualities that could potentially make these players Major Leaguers. Guys I’ve included in Tiers 3, 4, or not at all, I’d have an extremely difficult time inserting into any Top 10 ranking at this time. In the same breath, if you have someone that’s not on my list that you think belongs in Tier 4, I’m all ears! That tier can essentially go on for days!

Tier 1: Successful development means everyday Major League players

Tier 2: Successful development means back-end starters, impact or bulk relievers, or bench bats

Tier 3: Successful development means MLB depth or one strong MLB season

Tier 4: Plenty that catches my eye, but lots has to go right to find MLB success

Now let’s get to it, an incredibly important re-rank as we enter trade season — a time when multiple of these players will be included in deals for Major League talent and a time when it’s super important to understand where they rank among their peers in the Cubs farm system.

Tier 1

1. Owen Caissie | OF, Triple-A Iowa

What he can brag about: He has improved in nearly every single way from a year ago. The most important ways in which he’s seen changes include limiting chase and pulling the ball in the air. And he’s done so as he continues to hit the ball harder than all but 30 humans on planet earth. We talk about Ballesteros’ age all the time, but let’s not forget that Owen is playing his second season in Triple-A… at age 22!

How he can get even better: The lone part of Caissie’s game that hasn’t changed a ton from last year are the amount of whiffs he produces. It’s what leads to his high strikeout rates and, quite simply, striking out 30% of the time in Triple-A doesn’t instill a ton of confidence that he’ll keep that number below 35% in the bigs. It’s the last hurdle he’ll need to clear to be an MLB All-Star.

2. Moises Ballesteros | 1B/C, Triple-A Iowa

What he can brag about: With his unique ability to put bat on ball and do so with authority, Mo was put on this earth to swing a bat. I’ve never ranked someone I view as a DH/1B-only prospect in the top 10 of my lists, which should tell you how much I love his bat. I do think his defense has improved from where it was a year or two ago, and I think Craig Counsell is creative enough to work him into a three-catcher system in the big leagues.

How he can get even better: To feel more secure in his long-term role in the Majors, I need Bally to do one of two things: bump the in-game power up from 15-HR to 25-HR potential or improve the defense enough to be a starting catcher instead of a third catcher. I’m far more comfortable in predicting the former becomes a reality.

3. Jefferson Rojas | SS/2B, High-A South Bend

What he can brag about: This dude is 20 years old and will spend at least a couple months in Double-A this season. He bounced back incredibly well from last season – something we expected from him given his poor injury and batted ball luck. The power has arrived to pair with an impressive bat-to-ball skill and I think I’ve seen enough to say he can stick on the dirt, even if it’s not at shortstop.

How he can get even better: Rojas doesn’t quite have an elite trait, in my eyes. Contact, power, approach, speed, defense… It’s all really strong. But I want to see one of those skills really take a step up to the next level. It will be necessary because you don’t see a whole lot of starters in the Major Leagues without at least one.

4. Jaxon Wiggins | RHP, Double-A Knoxville

What he can brag about: Jaxon’s breakout this season is everything we could have dreamed of. Becoming a Top 100 prospect in baseball just a few months after we entered the season with plenty of question marks is practically unbelievable. We spend a lot of time as Cubs fans talking about fastballs with unique characteristics that offset a lack of velocity. That’s not needed with Wiggins. He’s got the good ol’ fashioned country hardball that fans who don’t like data deep dives absolutely love. And who couldn’t fall in love with a heater that sits high-90s and touches triple digits?

How he can get even better: His fastball is great. His slider is great. That’s enough to be a big league reliever. But as is the case with most big-time prospects, the question is if he can develop a third pitch to stick in the rotation. But unlike someone like Ben Brown, who needs to come up with a pitch to get lefties out, Wiggins already has a changeup that has flashed plus. The changeup is going to be the moneymaker. We need to see it with more consistency and used with more confidence. If he can do that… oh buddy.

5. Kevin Alcántara | OF, Triple-A Iowa

What he can brag about: He’s once again riding a hot streak after a slow start to the season. It’s something he’s done for basically each of the past three seasons. He’s a great athlete, hits the ball really hard, can run the bases and play terrific defense. The Jaguar is simply a VERY good baseball player.

How he can get even better: There is basically just one thing keeping Alcántara from having an argument as the number one player in the system — his inability to hit sliders. If he gets extended run in the bigs, he’s going to be exposed by pitchers that can follow a scouting report and place that slider diving out of the zone.

Tier 2

6. Jonathon Long | 1B, Triple-A Iowa

What he can brag about: At the plate, Jonny Long is about as fun as they come. He hits the ball extremely hard and his bat-to-ball skills are very impressive, too. He’s a model result of the draft model the Cubs have leaned on the past few years for a data-driven approach.

How he can get even better: He’ll need to do one of the following two things to be a Major League starter: Option 1 is to prove he can play third base or left field, something the Cubs haven’t showed much faith in as he’s gotten little run anywhere but first base. Option 2 is to become a true slugger that can hit 30+ homers in the bigs instead of 15+.

7. Brandon Birdsell | RHP, Triple-A Iowa

What he can brag about: He’s back from injury and immediately becomes depth for the Chicago rotation. The stuff has looked similar in his rehab starts to what it did last year in his Cubs MiLB Pitcher of the Year campaign.

How he can get even better: With Birdie, it’s not about adding a plus pitch or velo like we typically talk about with lower level pitchers. If he can just continue to locate, improve his stuff the tiniest amount, and take to sequencing tweaks in the bigs, I think he can be around for a long time.

8. James Triantos | 2B/CF, Triple-A Iowa

What he can brag about: Despite the numbers being down a bit this year, I still think JT kinda is what he is at this point. His ability to play both 2B and CF make him a MLB bench player that logs more games than a typical bench guy. His unique talent to put bat on ball makes him a little slump proof and a good pinch hitter option. His speed and base running ability makes him an ideal pinch runner. He’s got a role in Chicago as soon as next year replacing Vidal Brujan.

How he can get even better: I can’t help but think there is a little more in the tank here. Triantos isn’t a small dude so he should have some more pop in that bat, but it will have to take a pretty extreme approach overhaul for him to learn to swing at pitches he can do more damage with. Even still, we’re talking a difference between 200 and 400 MLB plate appearances per season.

9. Cristian Hernández | SS, High-A South Bend

What he can brag about: His defense and baserunning are tremendous. The bat is looking a bit better this year than last. And last year it looked better than 2023. He’s just slowly but surely improving, albeit in a year where the Cubs have a Rule 5 decision in the offseason. To add or not to add to the 40-man roster will be entirely dependent on how he performs in his ultimate call-up to Double-A this year.

How he can get even better: In the cop-out of all cop-outs, I’m gonna say that Cristian doesn’t look hitterish enough for me. When he pulls the ball in the air, I can see a concerted effort from him to do so. Same goes for when he goes the opposite way or protects with two strikes or sits offspeed instead of fastball. I love that he does each of these things, because he wasn’t a couple years ago, but I want it to look second nature to him. Put all of these elements together into a damn good hitter. 

10. Christian Franklin | OF, Triple-A Iowa

What he can brag about: Christian still has arguably the best plate approach in the entire system and his defense has taken another step up, now as a very strong defender in all three outfield spots. His power has been on display more than it was a year ago and he’s not too far off from being an MLB-quality 4th outfielder this second.

How he can get even better: There is still room in his game to pull the ball in th air more. He currently sits in the 6th percentile when it comes to that facet of his game. While doing so typically coincides with making earlier decisions, which then negatively impacts a player’s chase rates, Franklin can afford to chase a bit more (currently 93rd percentile) if it means he’s doing a bit more damage.

11. Will Sanders | RHP, Triple-A Iowa

What he can brag about: The system has performed incredibly well this year, with breakouts (Wiggins), bouncebacks (Rojas), and big numbers (Ballesteros, Caissie, Long). I think that has really overshadowed what we’ve seen from Will Sanders this year. The numbers were significantly better in Knoxville than they have been in Iowa, but the way in which he’s getting outs is both unique and effective. His pitches dance across the zone, missing barrels by darting both horizontally and vertically just enough with every offering.

How he can get even better: That pitch movement needs to take the next step. The cutter needs to go from off the end of the bat to out of the reach of a righty hitter. The heater needs to carry even more above the zone. The splinker needs to touch dirt. Doing so will transfer Sanders from a crafty righty to a whiff artist.

Tier 3

12. Ryan Gallagher | RHP, High-A South Bend

The swing-and-miss is clearly there in a big way for Gallagher. That’s my number one indicator when evaluating a pitcher and he passes with flying colors. Gallagher was hardly on my radar entering the season despite being the Cubs’ top pitcher selected in last year’s draft, so I’d love to see more track record. He belongs in Double-A for the second half of the season.

13. Nick Dean | RHP, Double-A Knoxville

I had Dean above Gallagher until just before I hit publish on this piece and the two remind me of each other quite a bit. Less whiff since his Double-A debut a few weeks ago but I still believe in the stuff, at least as a reliever. Ignore the ERA north of 5.00, under the hood he’s been much better than what that number indicates.

 14. Grant Kipp | RHP, Double-A Knoxville

Kipp rounds out this trio of “choose your fighter” starting pitchers and the slider is his carrying talent, in my eyes. It flashes terrific at times and although he’s 25 years old, the undrafted free agent from Yale is just now hitting his stride.

15. Pedro Ramirez | 2B, Double-A Knoxville

It seems a little silly to have a 21 year old in Double-A with an OPS+ of 116 and a K% south of 15% in this tier. His results have been very strong, not only this year, but throughout his professional career. This ranking comes down to projectability and with a lack of size and a simple approach at the plate where he doesn’t work many walks, I can’t see much more than a depth infielder riding the shuttle between Iowa and Chicago. It’s a profile that resembles Triantos, just a tick down across the board.

16. Erian Rodriguez | RHP, High-A South Bend

After a delayed start due to injury, Erian has come out posting impressive numbers, although it’s been with stuff that looks just the slightest bit down compared to when I watched him last year. This is a pretty flexible ranking for him, especially after he earns a promotion to Double-A within the next month or so.

17. Eli Lovich | OF, Single-A Myrtle Beach

The numbers ain’t pretty for last year’s 11th rounder, but the movements I absolutely love. You’re gonna have to dream with me on Lovich but I think he has a chance to follow an Owen Caissie path over the next few years in the Cubs system, both in terms of physical growth, hitting style, and improvements on defense in a corner outfield spot.

18. JP Wheat | RHP, Single-A Myrtle Beach

I actually had the fireballing righty up a few spots in this ranking before finding out he was added to the 60-day IL on Wednesday. That likely keeps him out for the rest of the season, and after poking around, I’m still not sure what the injury is. But a legit triple-digits fastball and nasty slider are enough to keep him in the Top 20.

19. Angel Cepeda | SS, Single-A Myrtle Beach

See Lovich, Eli re: bad results, impressive upside. Cepeda is talented enough defensively to stay on the dirt and despite the .632 OPS, doesn’t look overmatched at the plate. Remember, he’s in an impossible offensive environment and still a teenager.

20. Cole Mathis | 1B, Single-A Myrtle Beach

He’s missed a big chunk of this season due to injury and that’s coming off recovery from Tommy John surgery. I’ll admit that I’m super confused on Mathis and where to rank him. Deferring to the Cubs front office of a 2nd round pick seems silly for a college draftee more than a year removed from draft day, but here we are.

Tier 4

21. Carter Trice | UT, High-A South Bend

A second baseman turned catcher turned first baseman turned center fielder, Trice has shown off impressive power and a strong approach at the plate. I have concerns about his pure feel to hit, but trust that some of his athleticism will take over in that regard. This is one of the most impressive offensive players in the system this year and he deserves more pub.

22. Connor Noland | RHP, Triple-A Iowa

Let me break out ol’ reliable. I’ve talked about Connor plenty over the past couple years — whether it’s on my prospect lists or on social media or over on the pod (with him, even). He’s a really good Triple-A pitcher. One step up in stuff makes him a shuttle guy — a role I think he’d thrive in.

23. Nazier Mulé | RHP, Single-A Myrtle Beach

I think this ranking is representative of me believing in Mulé but not being as high as most fans are while also sitting here simply wanting more from him. I know he throws heat. I know he can go deeper in games now. He succeeded in getting more whiffs. Now let’s reign it all in, especially the 16% walk rate. 

24. Jose Escobar | OF, Single-A Myrtle Beach

I came into the year super high on Escobar and then he got off to a brutal start at the plate in his return to Myrtle. Since then, he’s turned things around quite a bit. Raising the average, working deep counts, logging a ton of walks. The power hasn’t proven itself like I expected it to, but it might take a promotion out of the Carolina League for that to happen. 

25. Nick Hull | RHP, Double-A Knoxville

Nick Hull the reliever is so much better than Nick Hull the starter and I was so disappointed when the Cubs started him in the rotation this year. Back in the bullpen, his numbers have been terrific, he gets tons of whiffs, and I think that he belongs in Iowa… now.

26. Riley Martin | LHP, Triple-A Iowa

You’re probably sick of hearing about Riley from me, and that’s fair considering I bring him up every chance I can. But he’s so, so good in the Iowa pen. He walks too many batters, it’s true. Way, way too many. But every single other thing he does is marvelous. His fastball-curve combo is outstanding and hitters simply can’t touch him. 

27. Owen Ayers | C, Single-A Myrtle Beach

He’s super old to be playing in the Carolina League (3.6 years older than the average hitter) but his combination of athleticism behind the dish reminds me of Bryce Windham and gap-to-gap pop reminds me of Jared Young. Age doesn’t matter with catchers the way it does other hitters, so I’m okay letting him take his time developing en route to a much older MLB debut as a backup catcher someday.

28. Matt Halbach | 1B/3B, Single-A Myrtle Beach

Simply put, I really dig Halbach’s swing and think he might be good enough to stick at third base a bit as he climbs the ladder. I’d rather a bat-first 22 year old be beating up on younger competition a bit more but visually, I like what I see.

29. Tyler Schlaffer | RHP, Double-A Knoxville

This is super fun. After years of injuries and inconsistency dating back nearly five years, the Homewood-Flossmoor grad put up one of the most dominant months of pitching I’ve seen during my time covering this system. Over his final five starts in South Bend, Schlaffer posted a 0.53 ERA by giving up just 12 hits in 34 innings. He then got bumped up to Double-A and logged two straight one-run outings. I’m mostly chalking the success up to the Danny P Effect — pitching with confidence and terrific sequencing.

30. Ethan Flanagan | LHP, Single-A Myrtle Beach

Let’s use this last ranked spot to throw some love Flanagan’s way. Making his full-season debut two years after being drafted, he’s featured a good fastball-slider-changeup combo from the left side in his handful of starts. Now healthy, he could be a fast mover.

Draft Picks

To stick with my self-imposed thresholds of only including players that have thrown in full-season games, this year’s draft picks were not included in my rankings. But if I were to do so, here’s generally where they would be included:

  • 1st round pick Ethan Conrad somewhere between 5th and 8th, likely just before or after Kevin Alcántara.
  • 2nd round pick Kane Kepley somewhere between 18th and 27th.
  • 6th round pick Josiah Hartshorn somewhere between 19th and unranked
  • 4th round pick Kaleb Wing somewhere between 21st and unranked.

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