Theo Epstein on Joe Maddon, David Ross, Nicholas Castellanos and the Cubs’ future

Theo Epstein heaped so many accolades on Joe Maddon during his end-of-season news conference that I half-expected Joe to step out of the wings behind the backdrop and for them to announce, “Only joking! Joe’s coming back!”

That didn’t happen, of course, and later in the nearly 90-minute session with reporters, Theo elaborated on his thoughts on Maddon. He said that Maddon was the right hire in 2014 for the particular group the Cubs had at that particular point in history. Remember what I said in my reflections piece earlier today?

I’ll note that I don’t think [Jon] Lester comes to the Cubs if Joe Maddon hadn’t been hired as Cubs manager in October 2014. The Maddon hire was the sign to everyone that the Cubs were serious about winning right now. If Maddon’s not Cubs manager for 2015, I think Lester signs with the Giants, who offered him more money and sent Buster Posey to Lester’s Atlanta-area home to say, “I want to be your catcher for the next six years.” (Yes, that actually happened.)

I truly believe that. It was one of the best serendipity moments in Cubs history — Lester, one of the best free-agent signings in franchise history, available at the exact time Maddon was. That’s the sort of thing Theo was talking about. He went on to say that if he had a group like that at this moment in time, he wouldn’t hesitate to hire Joe again, but that he felt a new voice was needed for this group at this particular time. He said, “For this group change is important,” and I don’t think any of us can argue with that.

For the rest of the session, a lot of the things Theo mentioned are things we already know:

• David Ross is under consideration for the managerial spot, but Theo added that despite Ross “having a lot of things going for him,” connections to the current team are not necessarily important, and “he’ll be evaluated on the merits.” As he should be.
• So is a “current member of the coaching staff.” I’m going to presume that’s Mark Loretta, though Theo would not specifically say so. I can’t see anyone else on the current staff that would be qualified.
• A coach or manager from a team currently in the postseason is someone they’d like to talk to. Since I haven’t had the time to look at the staffs of 10 postseason teams, I won’t guess. Feel free to speculate, though. Theo said he hoped to begin interviews “next week.”
• The Cubs would love to have Nicholas Castellanos back. Theo said “I love everything about Nick Castellanos,” and lauded Nick’s “production, consistency, team-oriented approach, passion and professionalism,” but he also noted that Castellanos has “worked hard to get to free agency” and wasn’t sure the team could bring him back. Personally, I do think they will take a hard look at doing it.
• Regarding Nico Hoerner, Theo gave him great credit for coming into a “unique situation” and performing well, and added “he could continue development at the major-league level,” citing players around the league around Nico’s age who have produced. He didn’t mention names, but I will: Juan Soto, Ronald Acuna Jr., Yordan Alvarez.
• Craig Kimbrel was said to be “upset” with his performance down the stretch, but he won’t need surgery and will “benefit” from a full spring training. On the bullpen in general, Theo said, “Our inability to pitch in high-leverage situations haunted us throughout the year.”
• He said there were “no untouchables,” though he would love to keep Kris Bryant and Javier Baez around and will look into contract extensions this winter. But he again noted that the team can’t look backwards, and that’s often been a problem for some in the organization given the success in 2016. Cubs people thought, “Well, we succeeded when we did it that way,” but times and players change and you have to adapt to new circumstances.
• Epstein said the Cubs have “unacceptable numbers from the leadoff spot.”

The talk often turned back to Joe Maddon. Theo said the “right” manager would “ask what made Joe so successful. Again, it made me wonder whether Joe would turn around the corner and give us a 2016 Dexter Fowler-type surprise.

But that’s not going to happen, nor should it. Theo is right. This group is different now. If David Ross is in fact hired, there are just 12 men left on the end-of-season 40-man roster who were his teammate: Kyle Hendricks, Jon Lester, Pedro Strop, Willson Contreras, Anthony Rizzo, Ben Zobrist, Javier Baez, Kris Bryant, Addison Russell, Kyle Schwarber, Jason Heyward and Albert Almora Jr. Several of those players could be gone in 2020 from retirements, trades or free agency. It really is a different group, even with (say) a core of Rizzo, Baez, Bryant and Contreras remaining, and it’s even possible that one of those guys could be traded. Ross would have no problem asserting authority over that sort of group.

Late in the session he was asked about self-criticism. This was important, I thought, because I think many of the issues with this team exist because the front office failed in their role. Theo said he thought he was building an “unstoppable force” and that the FO gave up a lot of resources doing so. That likely refers both to money and the trades of prospects like Gleyber Torres and Eloy Jimenez. And he said, “You’ve got to hit on deals.” This is something they did well pre-2015, as I had noted in my reflections piece:

The acquisition of Jake Arrieta and Pedro Strop for Scott Feldman and Steve Clevenger was one of the best trades in Cubs franchise history. Outstanding value was brought to the North Side in the trade of Ryan Dempster for Kyle Hendricks, as well as the deal that brought Dexter Fowler to the Cubs for Dan Straily and Luis Valbuena. And acquiring Anthony Rizzo for Andrew Cashner not only produced great results on the field, but got the Cubs a beloved player who is a franchise icon.

All of those trades were made before the contention window opened in 2015. Since then many trades made by Theo & Co. have failed.

So I think many of the criticisms we’ve had about the way this front office has operated the last couple of years are things they have noticed about themselves. Theo said the team will be hiring a Director of Hitting and Director of Pitching to keep the organization on “the cutting edge.” We should hope so.

Lastly, he challenged every player in the organization: “We want to compel every player to be the best he can be, to be the best version of himself.” Implicitly, this says that hasn’t been happening the last two years. We can only hope it will going forward.

It is just 144 days until the spring opener February 22, 2020 and 177 days until the Cubs take the field against the Brewers March 26, 2020 at Miller Park. (Go ahead, click on those links, they’re countdown clocks that will reside on the front page of this site all winter.)

Those dates will arrive faster than you think. Theo & Co. have a lot of work to do. Onward.