First, let me say I am not against Ross in any way. I loved him as a player on the '15-'16 Cubs. and I think the team has been missing his particular style of leadership. This farticle (See Glossary for Farticle definition)is not an indictment of Ross or his potential managerial skills. Truth be told, I had him in a tie with Espada as my choice to lead but I would have been perfectly fine with any of the options (except Babe Kapler).
Here's the thing about Ross, for better or worse he is undeniably a Theo/Jed guy. While we don't really know how the inner workings of the team are going to go, it is expected that Ross will follow Front Office suggestions more rigidly than Maddon did. Now, I'm not saying Ross is going to be a puppet of the Front Office, far from it. He will do things his way most of the time, but as the new guy there will be times he'll have to defer to Front Office. It's a fairly common business practice, hire someone inexperienced, pay them less than an established hire, and mold them into the employee that best fits your organization.
The Front Office since the rebuild?
This is now 100% Theo's team.
You may not have noticed (lol), but the Front Office isn't exactly batting 1.000 these days. The big money free agents and big trades have returned a resounding 'meh.' Lester has earned every bit of his contract, but last year was not pretty. I won't re-litigate the Chapman trade because it was an obvious need and the Yankees knew it. It's the price you pay for breaking a 108 year curse. However, the Heyward, Chatwood, and even Darvish deals have had middling results so far. Quintana has been solid, but they gave up a lot for 'solid' performance. Even the guys that came over and performed well seemed to be gifts more than scouting wins. Hamels' ERA in Texas was nearly 5!! when he was acquired. In his last 4 starts before coming to the Cubs he pitched 17 innings and gave up 21 ER! That's an 11+ ERA! Yikes. With the Chatwood and Duensing failures they needed Monty in the BP and a starter to give them innings. So, they got Hamels on the cheap. Similar story with Castellanos (IMO), sure he fit a need but they certainly didn't outbid anyone for him. They were lucky that his defensive shortcomings were diminished playing in a smaller Wrigley Field. Absolutely no one saw him going off like he did, either. The one place where they've struck gold more than once is in the BP reclamation projects. Wick, Wieck, and even Mills were absolute revelations last season. If they can replicate anything close to those numbers in 2020, the Cubs bullpen will be in much better shape.
Winning another World Series is the goal now, Epstein & Co. moved the goalposts and haven't been able to replicate their 2016 success. So, Theo looks to be calling more shots this year. Does that mean he keeps Ross from putting Heyward or Almora in the leadoff spot? Maybe. Does he keep Ross from putting Kimbrel into a high-leverage save the day he comes off an extended injured-list stint? Maybe. One thing is clear, if Ross gets essentially the same roster for 2020, then I don't see much changing for the Chicago Cubs. The team has flaws that need to be fixed and that falls on Theo. If they aren't fixed and the team underachieves again, then there is no one else to point the finger at. The finger will be pointing directly at Theo and might force a change from the Ricketts family.
This has been the Golden Age of Cubs baseball and I'm not ready for what the team looks like post Epstein. So, I'm rooting like hell for Rossy because I like him a lot, but also because it might mean a rebuild and regime change if he fails.