It's an interesting situation for sure because it has been a LONG time since the Cubs had any kind of starting pitching prospects in the pipeline that have amounted to anything. The 2016 WS team was constructed by buying pitching to go with the top end positional talent they had but this rebuild should be a little different as they have some guys that could fill the pitching needs and not have to go out and buy several arms. I do think they need to spend on that surefire #1 Ace for the rotation as at the moment I don't think any of the guys in the system are going to be of that caliber but could turn into good middle to back end rotation guys. Maybe 1 of them surprises us, its too soon to tell. If you look at that 2016 rotation Lester was the big piece they brough in 1st, they traded for Arrieta during a sell off and got him because he couldn't throw strikes for the Orioles, Hendricks was a prospect that came from the Dempster trade if I recall and Lackey was a free agent signing at the tail end of his career. There really were not a lot of home grown guys on that pitching staff, Hendricks and Carl Edwards Jr were basically it.
Just need to be smart about it and not trade or sign for some marginal guy like we did when we traded for Quintana in 2017 thinking he could be a top half of the rotation guy. The Cubs have options internally already to fill the back half of the rotation but Stroman and Hendricks are not #1 guys and I'm not even certain either are #2 guys on a good team either. It's Hendricks last year of his contract in 2023 so they could be moving on from him soon too.
If you look at the Cubs top prospect lists from 2015-17, two things really jump out. The almost historic amount of position player talent, not just the top end type of talent that came up but the depth too, the Vogelbach's, Caratini's, Candelario's. Guys that didn't turn into stars, but became long term MLB guys. It's not normal to have position player after position player into the 20's and 30's of a teams prospect list all stick in the majors.
The other thing, is their complete inability to develop any pitching internally. Duane Underwood, Pierce Johnson, Bryan Hudson, Jake Stinnet, Oscar De la Cruz, Thomas Hatch, they missed on pitcher after pitcher. Forget developing top end guys, that weren't even able to develop 4th/5th starter types or back end bull pen guys. Carl Edwards was the one exception, Dylan Cease made it but that was after being traded and now Steele is showing promise. Not having solid pitching options internally puts a lot of stress on needing to nail free agent signings to bolster the rotation, and when you start missing on guys like Chatwood, or have to part with high level talent to acquire mid-rotation pitching, that competitive window can close quickly.
