It’s been two days since the minor league season ended and I’m starting to get a lot of little things done in the house and out in the yard before winter comes. In the meantime, we’ve got a lot of things brewing over here at North Side Bound over the next month. Here’s a little preview of what’s to come in October.

We will be putting out our players of the year post at some point. That will also have our awards for the year. The voting process has been very interesting. Starting around Columbus Day, we will do the affiliate reviews for the year. And, as usual, I’ll have my top storylines for 2023 dropping the week after. Those will be broken down by hitting, starting pitching, relievers, and the draft.

Will also have an article about impending minor league free agency as well as our own picks for the 40-man roster.

We will also be ramping up next month to celebrate our one year anniversary of North Side Bound on November 1st. 

And in the Halloween spirit, we will be doing some mail bag posts and roundtable sessions to answer your questions all fall and winter. You can send us a question in the comments down below or you can email us at or over on Twitter.

Disclaimer – We get a lot of questions and yours might not get answered until February, but we will do our best to get to them all. We will do the more timely ones on the Rule 5 Draft and 40 man decisions first.

“The Weekly” will still be doing its thing on Sundays in October except it’s going to be mostly about the happenings in instructs and the Arizona Fall League. That begins in two days.

When November comes, we will have the “as of yet unnamed off-season series” that starts the Tuesday before Thanksgiving. In addition, I will be breaking down each position group in the system over the course of two months starting the Wednesday before Thanksgiving. And my annual Top 20 Prospects Under 20 will be out at some point. Greg Zumach will be doing some interviews at some point.

As for when our prospect lists will drop, we’re not yet. We’ve got a lot of things going on in our own worlds. Making a list is a huge time commitment. We will have them but it may not happen until December at the earliest. Then again we might get a wild hair and spit them out in a couple of days. We shall see.

We will be covering the Rule 5, trades for prospects, trades with prospects, MiLB free agency, IFA news, prospect lists, and any other breaking minor league news of any kind all winter. The return of the Cubs Convention this winter is also in play!

It looks to be a busy offseason starting with just October!