Theo Epstein Says Roster Change ‘Warranted and Necessary,’ Expects ‘Status Quo’ for Leadership Structure

Theo Epstein addressed the media Monday afternoon for yet another postmortem press conference that took place far too soon after the close of the regular season. Maybe it’s a good thing this one wasn’t broadcast live as those in the past have been, since it meant beat writers with access to the Zoom meeting could provide a filter for the public. Not that most people hadn’t already predicted the content of the proceedings with a strong degree of accuracy.

Epstein noted that there would be no exit interviews this week as is typically the case, but that the club wanted all players and staff to spend some time decompressing and processing the season. Given all that’s happened and the way things ended, it’s reasonable to believe Anthony Rizzo isn’t the only one feeling numb, so it’s probably best to let things settle for a bit. They’ll circle back up about a week later than usual to conduct the business of officially closing everything out from a procedural standpoint.

One discussion that will likely take place well before the rest is between Epstein and Tom Ricketts on the future of the Cubs’ leadership structure. The baseball boss downplayed any greater significance in light of a recent report that he could see fit to exit prior to the conclusion of his contract in 2021, saying this is something they do every year. He did, however, acknowledge the obvious reality of the situation.

“I’m a Cub,” Epstein said. “The status quo is the most likely outcome, but it’s just realistic at some point there will be a transition.

Theo on his future: meet with ownership after every season. thorough evaluation. "Those are meetings we are looking forward to." …"We do that every year." "I am as invested as our leader in baseball ops as in any point in last 9 years." .. "My expectation is that I'll be here."

— Mark Gonzales (@MDGonzales) October 5, 2020

As for just how far the status quo will stretch, well, that was another topic of conversation. Epstein wouldn’t address specifics when it came to staff or players other than Jon Lester, whose future with the organization is TBD, but he did say “some change is necessary and warranted” after the Cubs “were getting beat by fastballs in the strike zone” and didn’t do a good enough job of adjusting.

“Simply hoping for a better outcome going forward doesn’t seem like a thoughtful approach,” Epstein admitted.

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True though that may be, it didn’t seem like a very thoughtful approach in either of the past two or three offseasons, yet here the Cubs are. The offense that “broke somewhere along the lines” in 2018 hasn’t been meaningfully addressed and the prolonged failure to develop impact pitchers continues to dog the organization. The budget still has a great deal of uncertainty but figures to be limited, potentially hamstringing them when it comes to those necessary outside additions.

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And make no mistake, the Cubs do plan to acquire more pitching depth rather than look primarily to the farm system to replace as many as two or three starters depending on how you look at it. Even with four starters seemingly in place for 2021, Epstein indicated little faith in the system to produce even one more viable starter or even significant rotation depth.

“We certainly have to seek starting pitching and starting pitching depth from outside the organization,” he admitted.

Look, I’m only reading tweet leaves here since there’s no way the Cubs would ever grant me access to the media Zoom, but this strikes me as the most damning portion of the 2020 autopsy. Yes, swinging through fastballs and scoring just one run across two playoff games is very, very bad. But when teams across MLB were using the truncated season as a way to develop young pitchers, something the Cubs have repeatedly acknowledged is an organizational shortcoming, the North Side saw just two big league debuts.

Only one of those came in a start, when Tyson Miller took the mound for two innings as part of a doubleheader on August 17. He appeared in one more game on September 5, pitching three innings of relief against the Cardinals. The only other young hurler to button up a Cubs uniform for the first time was Brailyn Marquez, whose outing on the final game of the season felt more like a toldya-so bone for fans who’d demanded his promotion.

The team can point to the recent overhaul of its pitching development infrastructure under the guidance of Craig Breslow, the smartest man in baseball, but that’s not a viable excuse at this point. Even though it’s only been a year since Breslow’s department really came to fruition and the lack of a minor league season seriously hampered their efforts, we’re talking about nine years of next to nothing from the system when it comes to pitching. The same could be said for non-first round draft picks.

In all likelihood, the Cubs’ system will begin producing legit MLB-level starting pitchers over the next two or three seasons as their more aggressive philosophy finally yields results. Thing is, they’ve got to spend money on the rotation in the meantime, money they may not have a whole lot of. They’ve also got to bolster the position-player core and maybe even extend a player or two. You know, with the money they don’t have because baseball just isn’t very profitable.

Everything boils down to having a ton of belief in their core players, something that may have hampered the team’s evolution in the four seasons since they won it all. There’s been this expectation that improvement would come from within, whether from natural maturation or the looming threat of a reckoning that never came. That obviously hasn’t worked, at least not to the extent most folks would have liked.

“We’ve had a lot of belief in this group, to our benefit,” Epstein said. “And if one wants to turn that around and say that’s been to our detriment the last three Octobers? I can own that, too.”

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Taking more of a broad view reveals a team that has qualified for the postseason in five of the last six seasons, a run most Cubs fans would never have dreamed possible even a decade ago. The fact of the matter is that Epstein and his crew have set the bar so high that there was little option but to fall short of it in subsequent attempts. Therein lies the problem, since each of those perceived failures are appraised more harshly than the last.

It’s the winner’s trap, as Epstein said last season, something the Cubs fell into in 2016 and can’t seem to escape. How hard have they really tried, though? That’s the question we still may not get an answer to this winter, whether it’s because they can’t or simply don’t want to affect meaningful change to the roster. But who knows, maybe being in the final year of his contract will spur Epstein to be a little bolder in the way he structures his team.

One thing’s for sure, we’re not going to go wanting for opinions on the matter however it ends up shaking out.