10 Topics to Follow During What Could Be Interesting Offseason for Cubs System

Four of the Cubs’ seven minor league squads wrapped up their seasons over the weekend, so only Iowa and the two Dominican Summer League teams will be playing for the next two weeks. It’s been a pretty transformative year for the system due to the influx of talent via international free agency, the draft, and, of course, the trade deadline.

It led to some pretty exciting baseball down the stretch in August and September as social media was abuzz with homers from Alexander Canario, James Triantos, and Kevin Alcantara. But just because the regular season is winding down doesn’t mean we stop following the Cubs prospects, so here are 10 things to look for between now and next season.

1. Who ends up in the Arizona Fall League?
The Cubs usually send seven or eight players to the Arizona Fall League to play for the Mesa Solar Sox, but they have yet to announce a single player for that assignment. They may use the next two weeks to make some determinations on some guys who recently came up to Triple-A and will be getting an extra two weeks of play. Pitcher Bryan Hudson is eligible to become a free agent after this season and the Cubs could use time in Iowa and Arizona to determine if they will add him to the 40-man.

I would also love to see Canario and Luis Vazquez go to Arizona along with guys that have missed some time this year. Canario could really benefit from learning how to be a more patient and selective hitter against advanced competition. It could help give him a headstart for 2022 or a peek at the pitching he’d face when he gets to Double-A at some point next year. Vazquez missed basically three months, came back to South Bend, and got promoted to Tennessee. He’s a physical specimen and an outstanding defender, the bat just needs experience.

2. The 40-man/Rule 5
The Cubs have some tough choices to make as to who they add for the 40-man roster. Some of those players are already at Iowa, including Ethan Roberts and Jared Young, while Vazquez and Nelson Velazquez are at Double-A. We could even see the Cubs dip down into High-A to protect relief pitchers Danis Correa and Eduarniel Nunez, who other teams are said to covet for his off-the-chart pitching metrics and spin rates.

Injured players like Jack Patterson and Riley Thompson are probably safe bets to leave off because they missed the entire year due to injuries. Look for this list about mid-November.

3. Minor league free agency
The Cubs have about 45 guys who are set to be free agents five days after the World Series, only some of whom they’ll keep by adding them to the 40-man roster. Dakota Chalmers is one possibility, as is Donnie Dewees. Most of the pending free agents who were with Iowa will probably be let go as the Cubs have plenty of other prospects to fill out the roster next spring.

4. Winter Ball
The Cubs have a lot of guys who should be playing somewhere this winter, whether it is in the Dominican, Puerto Rico, or Mexico. Chris Morel is a prospect who could benefit by getting some more experience in the Dominican, while other players just need to make up for lost time and could even end up in the Australian Baseball League right before spring training.

I talked to a few players at South Bend about that same topic and most of them at that level are going to be staying in Arizona this offseason to work on strength and conditioning rather than going back home.

5. Trades
The Cubs figure to spend at least a little bit of money after clearing roughly $100 million from the books, but they might be making more trades as well. That could mean either using their current talent in the minors to acquire players or further stripping down the major league roster to add more prospects. Even at this late stage of the season, it’s hard to tell what the Cubs are going to do with Kyle Hendricks, Willson Contreras, and Ian Happ.

6. Returning arms
This part of the article probably deserves its own post as the Cubs have a lot of prospects who should be returning from injury next spring. That’s going to clog up the starting pitching ranks at High-A and possibly Double-A, which might be a good thing in terms of built-in competition for spots. Pitchers are going to have to perform at their best from the get-go in the spring if they want a rotation spot.

7. Returning bats
Barring any setbacks in the rehab process, it looks like Cole Roederer and Pete Crow-Armstrong are both going to be ready for the start of the 2022 season. Now it’s a matter of where they will be placed next season. They might both end up in South Bend, which would be really weird for Roederer because he played there at Low-A in 2019, then played two weeks at High-A this year before getting injured.

8. The cuts
Because the Cubs signed so many free agents to fill up their rosters because of injuries, they are going to have far more players for the minors than what they actually need once the injured players come back. We could see some well-known names who have been around for 4-6 years end up out of the organization because their simply isn’t room with fewer affiliates and restricted rosters.

9. Coaching assignments
These usually don’t come out until right around Cubs Convention, which is in jeopardy for the second year in a row. Now that most minor league teams have already released their 2022 schedules, I’m wondering if the Cubs will actually announce their coaching staff a little earlier this winter.

Buddy Bailey should stay in Myrtle Beach to work with the young kids and I would not be surprised to see Michael Ryan move up to Tennessee as Mark Johnson gets back to his catching coordinator duties full-time. Marty Pevey should stay in Iowa while Lance Rymel gets a bump to South Bend.

10. Spring training with the big boys
In talking with some players at South Bend, one of their goals for next year was to get to go to the big league camp. Some were hoping just for a chance to play in an actual spring training game with the big league club or to work out alongside some big leaguers as they missed that opportunity this year due to COVID protocols. Unfortunately, many of those same protocols will probably be in effect again come February.

The focus was all on the big trades Jed Hoyer pulled off at the deadline to reshape the big league roster and refill the minors. Now it shifts to how the organization helps those prospects develop on their own journeys to Chicago, a strategy we’ll see playing out in earnest starting in October.

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