Brennen Davis – Photo via Chicago Cubs

Welcome back to the next installment of the offseason minor league mailbag. We have a lot of these to get through this winter so I decided today to go with something that’s a little off the beaten path. Let’s get right to it.

Cory Iwaszewski@CDub1519: The White-Sox quickly locked up Robert and Eloy before they made a name for themselves. Will the Cubs go this route this time? If so, who are your top 3 candidates to be locked up long term before they take over Wrigley? 

Thankfully, the Cubs really don’t have to make this kind of decision for a while. Although, they can start thinking about who they might want to do ahead of time. Next winter might be a better time to offer some young players extensions and buy out their arbitration eligible years. I can see the Cubs trying, I don’t know if they’ll succeed.

Number one would be Brennen Davis. He should be up in Chicago sometime this summer and I have no idea what kind a deal the Cubs would offer him. He’ll be all of 22 and if they do offer him a deal, it’s going to give him financial security for the rest of his life.

However, Davis will probably bet on himself and play out his initial six years and be a free agent at age 28. For me, the age thing there is a bit of a game changer. He could still come back at that point and get a 7 to 10 year deal with a lot of money if he’s able to produce at a high-level as a Cub.

If Justin Steele has a good year, I could see the Cubs plopping down some change and giving him some money that’s going to last him the rest of his life and his children’s’ lives. He might be the best pitching candidate to sign an extension right now. That way, he’s guaranteed a job in the majors whether as a starter or a reliever.

For both sides, though, 2022 is going to determine everything. If Brennen Davis comes up and struggles, which I don’t see happening, there’s no way the Cubs offer him an extension. If Justin Steele gets relegated to the bullpen by the end of the season, he’s out. The Cubs have no idea what role Adbert Alzolay is going to have her next year, let alone beyond. 

There’s still a lot of uncertainty to the future of the Cubs. One can sit here and say they will have this prospect or that prospect, but you never know how they’re going to do until they get to Chicago.

The White Sox gambled on both Eloy and Robert and the Sox hit both extensions out of the park. Both players got financial security and probably performed better knowing that the pressure was off of them to produce. They could just relax and play, which is probably the main benefit of getting an extension.

Over the next year, we’re going to see a parade of prospects make it to Wrigley. We could see Brailyn Marquez, Cory Abbott, Caleb Kilian, Ben Leeper, Ethan Roberts, Chris Morel, Nelson Velazquez, and Chase Strumpf all arrive by the end of 2022. That’s a lot of talent to go through and figure out just exactly who you want to extend. And for each and everyone of those prospects to get to Chicago, a lot of things still have to go right. 

There are no guarantees unless you get the extension. And if you think about signing that contract, you’re there in the big leagues. No more kicking and scratching for a roster spot. The pressure is off.

Thank you for the question, Cory, and it was a lot of fun to answer as it was quite different from the normal fare.