Fast-forward to late January 2021, and the Cubs will have added four top 30 organization shortstop prospects over six months. While the previous Cubs rebuild (years 2011-2014) received a tremendous amount of praise for prioritizing safe college hitters, the system’s underrated strength was the organizational backbone of shortstops. Much of this shortstop infrastructure was built before Epstein and Hoyer inheriting the organization. Starlin Castro (acquired by the previous regime and already established in the majors), Javier Baez (acquired by the previous regime), Gleyber Torres (international free agency-2013), and Addison Russell (trade in 2014) provided three legitimate upper-level shortstops coupled with a deeper prospect. All of these players were projected to impact the major league roster during the Cubs competitive win-cycle. Addison Russell, in particular, provides context on the actions of a rebuilding club. He was brought in despite the organizational presence of a stud third base prospect in Kris Bryant, an all-star SS in Starlin Castro, and an emerging force who put up a .920 OPS with 37 home runs the previous year in A+/AA in Javier Baez. We won’t delve into the subsequent events that derailed Russell’s life and career, but the trade informs the thought process of a rebuilding organization in Theo Epstein and Jed Hoyer’s mind. You can’t have too many shortstops.
Shortstop Influx
Ed Howard (SS- aged 18) was a surprise selection in the 2020 draft, but as I’ve written up before, “perhaps it shouldn’t have been surprising at all. Ed Howard possesses the skills to be an above-average and even All-Star shortstop for over a decade in the major leagues.” Howard has smooth infield actions and represents an elite pedigree as the top prep shortstop in his class. For all Ed’s traits on the field, he may be an even better person off the field. He is renowned for his makeup and spent time this offseason working with Jason Heyward, Curtis Granderson, and Nico Hoerner, on behalf of the Player’s Alliance to provide food to those in need in Chicago.
As the dust settled on the momentous Yu Darvish trade, beat writers, bloggers, and fans worked to distill down to the meaning behind targeting the specific players coming to the Chicago organization. Zach Davies made sense as a player who offset salary but is a perfectly cromulent starting pitcher. The remaining four players (all four aged 20 or younger) were far more surprising. Fans and analysts predicted the Cubs would acquire players who made their major league debut in 2020, such as Luis Campusano (C) and Ryan Weathers (LHP). The Cubs specifically targeted Reginald Preciado (SS aged 17), Owen Caissie (OF-18) Ismael Mena (OF-18), and Yeison Santana (SS-20) were all included in the deal. These four prospects are years away from impacting the Cubs at the Major League level, but reports are individually strong, especially for Preciado
The international free agency period that should have begun in July of 2020 was pushed back to January 15, 2021, due to the pandemic. The delay meant that the Cubs fans have had to wait for much-ballyhooed prospect Cristian Hernandez (SS aged 16) to sign with the organization. The hype train is intense around Hernandez. Comps range from Manny Machado to Javier Baez to Alex Rodriguez (who has a compelling case of being the best prospect of all time). Other prospect evaluators have tempered expectations labeling him one of the better international free agents. Even those prognosticators pumping the breaks on A-Rod comps, like Eric Longenhagen at Fangraphs still provide this excerpt from his write-up. Fangraphs writes “His infield actions are smooth and athletic, his swing has a gorgeous, pronounced finish, and he has the right amount of overt physical projection that may see him mature into the unteachable, star-making Goldilocks Zone where Hernandez stays at short and also has impact power.” Goodness!
Organizational Review
The Chicago Cubs already have five SS in the top 30 based on MLB Pipeline. Ivy Futures will provide updated top prospect lists after the International Free Agency period opens and players begin signing. MLB Pipeline includes Ed Howard, Reginald Preciado, Yeison Santana, Kevin Made (aged 18), and Rafael Morel (aged 19). The criminally underrated Andy Weber (aged 23) is not listed (#10 on Ivy Futures top prospect rankings). Neither is Luis Verdugo (aged 20; #18 on Ivy Futures ranking). Hernandez will soon be added in January, barring any snafus.
Not all of these shortstop prospects will end up at the shortstop position long term. The long-perceived belief is that since SS is such an athletically demanding position, players that play the position in the minors can more easily transition to 2nd/3rd/CF. Heading into 2021, I expect Andy Weber to be the starting shortstop of either High-A South Bend or (more likely) AA Tennessee. There is an intense grouping of shortstop prospects at the lowest levels. Yeison Santana may have the inside track to debut in High A South Bend due to age and experience playing stateside in 2019. Luis Verdugo is another candidate to get SS reps at High-A. In an ideal development situation, multiple players will perform well enough that their play warrants promoting to a higher level.
After those few, it becomes increasingly more difficult to project. Reports on Preciado out of San Diego instructs were extremely favorable. I’m inclined to bet that he is the most likely candidate to start at SS in Low-A Myrtle Beach in 2021. This leaves Ed Howard and Kevin Made as the rookie league starters at SS (AZL Cubs 1 and 2). I would not be surprised if the Cubs keep Ed Howard in extended spring training longer to continue to train on swing changes and get acclimated to professional ball. Similar to how he only played in a handful of instructional league games, Howard can continue to do a lot of work behind the scenes. Then again, Ed is an incredibly mature person and polished defender with hitting upside and overall pedigree. The Cubs may choose to challenge him on a full-season roster in his first full season.
The Chicago Cubs are entering a new phase in the organization. You can call it a rebuild or retool (or “recycle” for that matter). The organization does have a promising 2022 core of Brennen Davis, Brailyn Marquez, Miguel Amaya, Kohl Franklin, Andy Weber, and Ryan Jensen. Still, it appears that Jed Hoyer is also building out an even stronger wave behind that one (most likely 2024-2026 impact). That wave is not exclusively formed by its shortstops, but it is undoubtedly the 2024-2026 grouping’s premier strength. While not all of these prospects will succeed, developing one or two of these players into impact middle of the diamond MLB starters provides enormous value to the organization either on the field or as highly valued tradeable prospects.
Ivy Futures 
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