Hayden Wesneski – Picture by Dylan Heuer/Iowa Cubs

With September just two days away, it’s getting to be that time of year where we start talking about possible players the Cubs could add to the 40-man roster to avoid losing them in the Rule Five Draft or to minor league free agency. Currently, the Cubs have 70 guys who will be eligible to be taken in the Rule Five Draft and a little over 20 guys will be minor league free agents (click links above). How many spots are going to have cleared up to add is not very clear at this point.

In a normal year, the Cubs might protect three guys from the Rule Five Draft. But in recent years it’s only been one or two. With the amount of depth in the Cub system, there are at least 20 players who are going to warrant being discussed to add to the 40-man. The Cubs cannot protect them all and they probably can’t protect your favorite player. It happens. 

The wild card in all of this is other teams’ evaluations of the Cub’s system. If the Cubs internal scouting is off, they may value certain players that other teams don’t. They may also not value players other teams do. And that’s really the key to this whole process is getting your internal scouting right so that you’re protecting players other teams covet. If the Cubs really like a guy and other teams don’t, there’s no need to protect them

Let’s take a look at a collection of names in some unique categories.

The Locks

You can write their names down in pen because they are going to be protected. Brennen Davis, Kevin Alcantara, and Jeremiah Estrada are not going anywhere. 100%.

The Free Agent

With Javier Assad just being brought up last week, that sort of cuts this list in half. The only free agent I can see the Cubs bringing back to add to the 40-man to keep him from free agency would be Yonathan Perlaza. He has had a great season since May 1 when he began playing regularly. The switch-hitting outfielder will definitely be in the conversation for the November 18 deadline. If he signs a successor contract with the Cubs, he becomes Rule 5 eligible again. It’s a tossup for me.

The We Just Acquired You So We’re Gonna Protect You List

Both Ben Brown and Hayden Wesneski are pretty close to being locks considering the Cubs just acquired than a month ago. I really like what I’ve seen from Brown and a little bit what I’ve seen from Wesneski. Hopefully, the Cubs can tweak them a little bit this winter to make them even better for next year. The fact that these guys are a stone’s throw away from Chicago only helps their chances.

The We’re Going to Protect You So Other Teams Don’t Take You List

This is Danis Correia all the way. I would not be surprised to see him up in Chicago this month. For Correa, it’s a matter of controlling his offspeed stuff. He’s pretty close to being ready with his triple digit fastball.

The 50/50 List

If Ryan Jensen is left unprotected, some team is going to take him and stash him in the bullpen. If the Cubs don’t feel his future is as a starter, I really don’t know what is going on in Tennessee then. This year has been such a struggle for him. The Cubs recently changed his delivery so that there’s less moving parts, I don’t think they did all that just to lose him. I think they’d be willing to give him one more year to try and figure things out.

The Roll the Dice and Leave Unprotected List 

Riley Thompson, Andy Weber, Luis Vazquez, Nelson Maldonado, Bryce Ball, Yovanny Cruz, Luis Devers, Kohl Franklin, Darius Hill, Brendon Little, Michael McAvene, Yohendrick Pinango, Jake Slaughter, Cole Roederer, Cam Sanders, Chase Strumpf, and Jared Young are all names I could see the Cubs just rolling the dice on and not protecting.

The only one that might be tempting to add would be Devers just for the fact that he’s probably gonna be the Cubs Pitcher of the Year for 2022. Then again, what plays as a pitcher at High A doesn’t necessarily play at Double-A and that’s in the Cubs favor for not protecting Devers. The fact that he’s never pitched above South Bend and his fastball usually tops out at 91-92 continues to make him being unprotected more likely. Most teams are not going to take that low of a guy. If Devers threw 95, he’d be on the list. It’s a big risk but one the Cubs probably take.

Out of all the names listed, the number one Cub that’s going to go to another team if left unprotected is Darius Hill. For some strange reason, the Cubs have not figured out that other teams value that kind of hitter which is probably why he will be left unprotected because he does not fit in the Cubs’ boxes AND they are just flush with OFs who are almost ready. Hill is a player who going to be on base for you to drive in which is what you want. He does it with his bat. The Cubs, in all their blindness, just don’t get that as a value.

I could also see teams poaching Brendon Little as he does throw left-handed in the mid 90s. Those kind of guys don’t grow on trees. But do the Cubs really see Little as a future part of their pen? If they do, then they should protect him. And as soon as I typed that paragraph, he got called up for the Toronto series. So, we will see if this is going to be a long stay. If not, it may be time to move on.

The list should narrow over the next two months.

The next time we chat about this, a final predictive list should be ready.