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Chicago Cubs Top 20 prospects countdown: 16 to 20

Today’s rankings have one pitcher knocking on the door of the majors, one highly-regarded international signing and three former Padres.

Larry Kave/Myrtle Beach Pelicans

It’s day 2 of my annual trip through the minor leagues. It’s a trip that just one month ago I thought we wouldn’t be making together, but I’m glad you and I are along for the ride.

As I wrote yesterday, this year’s rankings are very difficult because of the twin problems of my not being employed here last year and the shutdown of the 2020 Minor League season. There is a lot more guesswork going into this year’s rankings than in year’s past. I hope you find them useful anyway. As always, any errors are my fault.

Today’s prospect rankings are brought to you by the letters “Y” and “U.”

Three of the five prospects listed today came over from the Padres in the Yu Darvish deal. It’s always hard for me to rank prospects who come over from other organizations. Unless they’re a big name like Addison Russell was, I’m usually not very familiar with them. I haven’t been following their trip through the system like I do with players already in the Cubs organization. So I’m going off of what others are saying and what video I can find on-line. This year I can’t even go back and watch their old games on What I have been able to figure out convinced me that all four minor leaguers in the Darvish deal are solid prospects, but where they should rank is much more of an art than a science. I imagine that in a few years I’ll look back and think I’ve either overrated or underrated all four of them, but by putting them where I have, I think I’ve got an even chance of being mocked in the future for being too pessimistic and being too optimistic. So that’s a good place to be.

Don’t worry. The fourth member of the Darvish trade is still to come.

Other than one pitcher who should make his major league debut this year, the prospects ranked today are all probably three to four years away from the majors. Possibly even more.

16. Yeison Santana. SS. DOB: 12/7/2000. B:R, T:R. 5’11”, 170. Trade with Padres (2020).

Santana is the player that I have the most nagging feeling that I’ve underrated, but I couldn’t justify ranking him ahead of any of the other players I’ll write about tomorrow, at least not based on my somewhat limited knowledge of Santana.

The Padres signed Santana for $300,000 out of the Dominican Republic as a flashy-fielding middle infielder with some potential to hit. After a season in the Dominican Summer League, Santana made an impression with his stateside debut in the Arizona rookie league as an 18-year-old in 2019. Santana hit an impressive .346/.429/.494 in 162 at-bats over 41 games. He struck out 38 times and walked 23 times, a solid ratio and one that I pay a lot of attention to at the lower levels of the minor leagues.

As a hitter, Santana gets his bat through the zone quickly and he can make hard contact. He rarely misses making contact at a pitch in the zone (from what I’ve seen) although like any young hitter, he can get fooled by a breaking pitch out of the zone. That should be fixed through experience. Some evaluations I’ve read think that he can grow into some power. I’m open-minded but skeptical on that point. I see him as much more of a line-drive hitter who sprays the ball to all fields, but it’s hard to see how the body and the swing of a 19-year-old will develop. So I’m not ruling out the development of power in the future.

Defensively, I’ve only been able to find about 15 seconds of him doing infield drills, but he looked really good in those. The on-line evaluations characterize his defense as smooth and sure-handed with above-average range and an average arm for a shortstop. No one thinks he’s going to have to move off of shortstop.

Anyone who has the potential to play a solid shortstop at the major league level has to be taken seriously as a prospect as long as they can hit a little. Santana looks like he could be one of those high-contact hitters that the Cubs have been chasing in recent years and that’s probably why they asked for him in the Darvish deal. But he doesn’t have great speed or much power at the moment, so he’s going to have to get on base a ton for him to be a starting major league shortstop and a bottom-of-the-order hitter. I’d feel more confident ranking him higher had he made Baseball America’s Top 20 Arizona League Prospects in 2019, but he didn’t. (Recently-traded Cubs prospect Pedro Martinez did make that list.) Even so, Santana is going to be one to watch this season, probably at Low-A Myrtle Beach. If he comes anywhere close to his 2019 numbers there, he’s going to rocket up the prospect charts.

Here’s some video of Santana at the Instructional League late last year.

17. Owen Caissie. OF. DOB: 7/8/2002. B:L, T:R. 6’4”, 190. Trade with Padres (2020).

The Padres took Caissie in the second round of the 2020 Draft out of high school in Ontario. He was a star on the Canadian junior national team and impressed scouts when he hit a ball over the batter’s eye at the Blue Jays’ Spring Training park in Dunedin, FL. The Padres took him in the second round (45th pick overall) of last June’s draft.

As you can see from those vital statistics or the video below, Caissie is a big young man who can hit the ball a long way. When Caissie gets his big long arms in motion and connects with a pitch, it makes a loud sound and it travels far.

It’s that making contact part that’s the issue. Caissie’s swing isn’t built for contact and as a Canadian high school player, he hasn’t had a ton of experience against top-level pitching. The Cubs have had some success recently tinkering with the swings of players and Caissie may be someone they think they can work with. He’s always going to strike out a lot, but if the Cubs can keep those strikeouts manageable, then he’s a potential 30 home run hitter in the majors.

One advantage Caissie has is that he was quite young for the 2020 Draft, having not yet turned 18 when he was picked. The Cubs can afford to be patient with him.

Defensively, Caissie is a corner outfielder with an average-plus arm. Despite his size, he’s quick enough right now to be an above-average defender, but I can certainly see how he could lose a step as he ages and he would have to move to first base. Hopefully that won’t happen until after he’s been in the majors for five-to-ten years.

Caissie has yet to make his professional debut, so he’s likely going to start the season in rookie ball in Arizona. I do expect that he’ll see some time in Myrtle Beach before the season is out.

Here is some video of Caissie with the Canadian Junior National Team.

18. Justin Steele. LHP. B:L, T:L. DOB: 7/11/1995. 6’2”, 205. Drafted 5th round. (2014), George County HS (MS).

Last year I ranked Steele as the 17th-best prospect in the Cubs system but warned that if he didn’t take a step forward in 2020, he’d probably fall off the list next year. Well, Steele didn’t take a step forward in 2020, but neither did anyone else on last year’s list, except Adbert Alzolay. Steele did play 2020 at the alternate site in South Bend and he got his first major league call-up, but he didn’t get into a game before being sent back to Indiana. At least he didn’t have the chance to call all his friends and family come to the game to see him not make his major league debut. When he returned to the alternate site, he suffered a hamstring injury and never got another chance at another promotion.

It’s unfair for me to say that Steele didn’t take a step forward in 2020 because from the reports out of the alternate site say that Steele did put in some good work in South Bend. While he has always been a starter in the minors, the Cubs had him concentrate on pitching out of the bullpen with the hope that he could be a left-hander out of the pen last year. It almost happened.

But out of the pen, Steele has reportedly added 2-3 miles per hour to his fastball, which now sits 94-96 mph in short stints. He’s always had that big high-70s curve ball that was his out pitch, but he’s recently developed a mid-80s slider that gives hitters a completely different look. Steele and the Cubs have claimed the slider is now his best pitch.

The big issue with Steele is that he’s never really been able to stay healthy. He had Tommy John surgery in 2017 and made a pretty miraculous return in just 11 months, but he struggled with control when he returned. That’s not uncommon, but it would have been nice to see if he had improved on that in 2020. The bigger issue is that his constant health issues may mean his body won’t stand up to the rigors of starting.

The Cubs still think Steele can be a starting pitcher in the long term, the short-term plan seems to be for Steele to be a left-hander out of the bullpen. His breaking pitches are certainly nasty against left-handed hitters and he probably will be good enough against right-handers to survive the new three-hitter rule.

Steele is on the 40-man roster and will probably start the season in Iowa, but his major-league debut (for real) is just around the corner.

Here’s video of Steele pitching in the Arizona Fall League in 2018. Remember, he’s just coming back from Tommy John in this video.

19. Ismael Mena. OF. B:L, T:L. DOB: 11/30/2002. 6’3”, 185. Trade with Padres (2020)

Mena was the player that I struggled the most about ranking. The scouting reports I’ve read make me think this ranking is too low. The admittedly very limited video that I’ve seen on him make me think this is about right. But he’s young and there will be plenty of time to rank him more accurately after he’s put in a year in the Cubs system. For now he’s here to make sure you keep an eye on him in 2021.

Mena was the prize of the Padres 2019 international crop, signing out of the Dominican Republic for $2.2 million. He was a tall, lanky center fielder with a line-drive stroke and some comparisons to Pirates outfielder Gregory Polanco.

If you watch the video below, you’ll see that Mena has a slashing, line-drive hitting stroke that complements his 70-grade speed. He strikes out a lot right now, but that could just be inexperience. At the moment, his hitting style is geared towards contact rather than power, but his frame could certainly add some muscle that could lead to double-digit power sometime down the road. I’ve seen one report that say he’s put on 7-10 pounds since signing.

Defensively, Mena projects out to be a plus center fielder with an above-average arm. The reports out of instructs say that he still has a lot to learn about reading fly balls and taking good routes to the ball, but he also hadn’t turned 18 yet and had yet to make his official professional debut. So let’s cut him some slack. He’s got a lot to learn but everyone writes that he’s a bright kid who takes instruction well, so there’s little reason to believe he won’t learn.

Mena’s upside is high — a strong defensive center fielder who bats leadoff or second, steals a lot of bases and hits with enough power that pitchers need to fear him a little. I have no idea how likely he is to reach that potential. He just turned 18 and he hasn’t made his official pro debut. Ask me again after this season. Mena is likely to play in Arizona in rookie ball this season.

Here’s some video of Mena with the Padres at instructs this past fall.

20. Ronnier Quintero. C. B:L, T:R. DOB: 11/13/2002. 6’0”, 175. International Free Agent (2019), Venezuela.

The Cubs signed Quintero out of Venezuela for a $2.9 million bonus, which was at the time a team record for the Cubs. (This year’s signing of Cristian Hernandez for $3 million has broken that record.) Some reports have compared hit to a left-handed hitting version of his fellow Venezuelan and fellow Cub Willson Contreras, but he has a long, long way to go before he’s to that point.

At the moment, Quintero’s biggest selling point is his left-handed power stroke. His short, quick batting stroke should give allow him to crush the ball to all fields and make enough contact for that power will show up in games.

The Cubs are convinced that Quintero can catch, but other scouts have their doubts. If Quintero has to move to first base, that hitting ability will be a lot less valuable. He runs well for a catcher, but the key phrase there is “for a catcher.” He wouldn’t run well for a corner outfielder.

Unfortunately, the shutdown of the minors last season means that all the unanswered questions about Quintero are still unanswered in 2021. I hope we get some answers as he plays in Arizona this summer and a Myrtle Beach debut is certainly not out of the question this upcoming season.

Here’s some video of Quintero taking batting practice. You can see what I wrote about Quintero last year and there’s a different video of him taking batting practice and making some throws from behind the plate. His arm looks good in that video.

Tomorrow: Prospects 16-20.