PCA and Owen Caissie – Picture by Todd Johnson

November is an awkward time of year. Until the World Series ends, there’s not really much to write about the Cubs farm system. However, for my brain, it always seems to be in overdrive thinking about random things and random players. Let’s  tackle a few things that have been bouncing around my head the past couple weeks before the offseason kicks in. 

Let’s get to it.

1. I really like Ben Brown. I think he’s a guy the Cubs can take and build him up a little bit, get him to use his lower body some more, and he could really take off next year. Or at least that’s what I’m hoping.

2. In just a few days after the World Series ends, both major and minor league free agency begins and we shall see quickly whether the Cubs are going to be a player at both levels. I would expect to see a few arms stashed at Iowa but not as many as in past years. If the Cubs really like their farm system, they won’t sign a lot of minor league free agent pitchers as MLB depth if they believe their own prospects can make it to Chicago in short order. 

3. When the 2023 season starts, Owen Caissie should begin the year at Double-A Tennessee. He will be all of 20 years old. I don’t think I can remember any 20-year-old being assigned to Tennessee as a position player since probably Javy in 2013.

4. There are some guys when you watch them in the minor leagues that just look completely different than everybody else on the field. Pete Crow-Armstrong is one of those guys. In being one of those guys, you can tell right away that they really don’t need a lot of development in the minors. I am not trying to rush Pete Crow-Armstrong to the major leagues. He’ll be there when he’s ready. I’m just saying he’s almost ready.

5. I hope Riley Thompson gets a shot at some point next summer. I was excited to see him return to action this year and to pitch really well the last two months of the year. How much he can adapt to Triple-A is a different story, but he is that close to being in Chicago.

6. The Cubs are going to expose a lot of guys to the Rule Five Draft. Then again, the other 29 teams are in the same boat. If a team take a guy, he better stick otherwise they have to return him. As a result, I don’t expect the MLB portion to be too busy for the Cubs, but the minor league portion of the Rule Five Draft will be nuts. Expect to see some lefty relievers added in that segment.

7. I don’t see the Cubs being big traders this winter. That might be more for next summer. Instead, I see them making a lot of smaller moves where they throw in a guy that pitched at class A. Those Double-A arms aren’t going anywhere. Free agency will be a different story.

8. I am on my fourth draft of my upcoming prospect list. It’s going to come out in a couple of weeks. I can’t begin to tell you what a mess it has been in trying to figure out where each prospect should be ranked. I started out with 35 guys and brought it down to 31. I left off some big names. Some of you will shake you head when you see it, but it’s just a list. There’s no need to get bent out of shape and curse and call people names because in six months, there’s going to be a new list with different names on it because some of the guys on this list are not going to be Cubs in the spring. Some are going to be traded and some are going to be taken in the rule five draft. Some will rise and fall. Some will graduate. Lists always change. That’s my rationalization that got me through making it.

9. I’m not good at hurrying up and waiting because that’s what I feel like the last half of October has been along with what the first week of November is going to be like. I am ready for off the hot stove season to crank up.

10. I am hoping to see Cole Roederer do well in Australia and have it carry over into spring training and the season. Still pulling for the kid to click.