5 Topics to Watch as Cubs Retool MiLB System This Winter

In most cases, there is not much to write about this time of year when it comes to the minor leagues. You might see some season reviews, prospect lists, or even some state-of-the-system type of pieces coming out on the Internet. However, things are gonna be quite different this off-season.

With Jason McLeod moving out of his former position and into a major league role after overseeing the past eight years of drafting and development, we’re going to see some changes in the minors. That starts well before June, as the Cubs will be organizing things throughout the system in order to rejuvenate their prospect pipeline

Under New Management

With McLeod out, it’ll be interesting to see how the Cubs structure their development hierarchy. Once Theo Epstein gets through finding a manager, he will move on to redoing the minor-league system. That includes naming the directors of pitching hitting he mentioned in his press conference, as well as revamping the scouting department and maybe even moving Jaron Madison out of the way as director of player development.

The new leaders will certainly be hired based on their ability to see eye-to-eye with the front office, but you can also bet on them having some new ideas. By their own admission, the Cubs have fallen behind other teams when it comes to developing talent and need to make some significant leaps forward.

Arizona Fall League Results

The AFL began a little earlier this year, which kind of moves up the timetable on a couple of things. Miguel Amaya is producing at a high level against elite competition, but he’s only playing a couple times a week. Where his stock stands could affect the decisions that are made at the major league level.

His defensive capability combined with his power make him either a valuable trade piece or someone the Cubs envision as being in Chicago by 2021, or 2022 at the latest. Come November 20, he will be on the 40-man roster at the age of 20. 

40 Man Decisions/Rule 5 Draft

Amaya is the only no-brainer, with just about every other prospect’s future likely up in the air. I could see the Cubs adding starting pitcher Colin Rea but I can also see them taking chances on leaving P.J. Higgins, Jhonny Pereda, Zack Short, Trent Giambrone, Dakota Mekkes. That’s going to be the first tell-tale sign of the direction this new management is going.

Are they going to roll with current prospects or are they going to want to go out and get new guys they value from other systems? The Cubs have 71 prospects eligible to be selected, plus another 23 MiLB free agents to decide whether or not to add. 

New Technology

Much has been made of the Cubs’ Pitch Lab, but it’s been too little and too late when it comes to developing pitchers. Bringing in a new Director of Pitching, a role like the one Driveline’s Kyle Boddy has filled for the Reds, likely means new technology to evaluate and train prospects.

In 2012, the Cubs thought they were on the forefront of tech being used in development. Now, the organization has fallen way behind the Astros, Twins, and Rays in that department. It’s good that they’re aware of their shortcomings, now it’s just a matter of integrating new concepts and getting results.


Once the new minor league leadership has been sorted out and they’ve done their evaluations of the players in their charge, they’re going to have to decide how aggressive to me with affiliate placements. For example Brailyn Marquez should be at Double-A Tennessee to start next year because there’s nothing more he can learn at Myrtle Beach.

The real questions are exactly where all of the big-armed pitchers they took in the draft last year end up. Will Ryan Jensen and Michael McAvene open at South Bend or will they make the leap to Myrtle Beach? Will Richard Gallardo get a shot at pitching full-season ball in South Bend at just 18 years old? 

McLeod and Madison talked before the 2019 season about needing to get more aggressive with their development timelines, particularly when it came to pitching. There isn’t a ton of pressure to produce immediate results, but the farm system will have to start feeding the big club before the core players’ contracts start expiring. Outside of Nico Hoerner and Adbert Alzolay, most of the Cubs’ top prospects are still a year or two away from being ready, so the organization really needs them to dominated at their respective levels.

While it’s on the players themselves to perform, the Cubs first need to put the right leaders in place to ensure that development is happening at the right pace and in the right places.

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