Cubs Enter Critical Offseason with Greatness on the Horizon

The Cubs are entering the most important offseason of the Theo Epstein era, perhaps—for this organization—the most important offseason of all time. While last winter was no doubt crucial—and the Cubs’ brass passed that test with flying colors in their acquisition of Jon Lester, Miguel Montero, and Dexter Fowler (among others)—this time around the front office will be looking to capitalize on the steps taken in 2015 and take the team to another level. Not just for 2016, but the foreseeable future.

“We need to raise the bar as far as the type of team we want to build and the path to being a great club, not just a good club,” Epstein said at his year-end press conference.

It seems odd to hear Epstein suggest that the team needs to raise the bar after a 97-win season and a run to the NLCS. That kind of performance alone immediately ups the ante from what this team and its fans have grown accustomed to over the past half-dozen seasons. But this group knows that they have to be aggressive at all times, and can’t assume that they can just ride a young, talented team back to the playoffs.

Even optimists like myself who believed this team could go far (once the summer really got going) realized this team was always flawed; an eight-game winning streak to end the season or a 21-4 stretch in August wasn’t going to mask those deficiencies.

“I do think that managing success can be really difficult, in part because you have to manage expectations,” Epstein told a room full of reporters. “You have to be really careful that you don’t have an organizational arrogance that takes hold or a sense of entitlement or a sense of complacency. But I don’t even think we’re there yet. We’ll deal with that after we win a World Series, we are not there yet.

“There’s so much we have to do just to maintain the level we accomplished this year, let alone improve upon it and win the ultimate prize. Nothing is promised in this game, nothing is promised in life. Teams that think they have these sure-fire five-year windows have often seen them slammed shut in front of them through bad luck or bad performance or bad decision-making. We don’t take anything for granted, we have to work our tails off to get back to a position where we have another shot at October.”

There is no doubt when you hear Epstein talk that he and everyone in the organization understand that this is their moment to capitalize on what they’ve built over the past few years. It’s not a time to be satisfied, but rather to be aggressive in trying to take advantage of the momentum created in 2015, and all the years leading up to it. Whether a team fails to make the playoffs or wins the World Series, improvement should be a constant goal.

And while they do have plenty of areas to upgrade, they also aren’t going to overreact to anything that happened in the postseason. Don’t expect Kyle Schwarber to get put on the trade market because he looked rough in left field. Jorge Soler won’t become untouchable because he went insane at the plate for seven games in October (but seriously, he should be given major props for stepping up and posting a .474/.600/1.105 line this postseason—yes, that last number is his slugging percentage).

Outside of specific needs—which we’ll address in the coming day here at BP Wrigleyville—there were two things I was curious about how the Cubs would be able to combat going forward. The first is this: this team was unusually healthy in 2015, only losing large chunks of time from two (maybe three, if you want to include the 22 games missed by Montero) players who were expected to be major contributors: Jorge Soler and Neil Ramirez. While it’s very possible that the Cubs have a great training and medical staff and manage to stay healthier than expected for years to come, it’s not something anyone should bank on.

The other concern is the assumption that the young players will automatically take a step forward in 2016. It’s easy to assume they’ll make that leap, yes, but the fact is development is rarely linear, and we could see a decline in performance from any of these younger players—well, to be fair, even the veterans as well, especially the ones with less of a body of work to rely upon.

Sure enough, Epstein and company are well aware that they can’t count on the illusion of constant health or youth developing on the most optimistic timeline.

“[We try] to anticipate everything that could go wrong, [and] that will get in the way of you being really good the next year or even better the next year,” Epstein said ,when discussing what his team looks at heading into an offseason when coming off a good season. “And then game planning for as many of those things as you can. Anticipating as many of those things as you can, trying to create as much depth, as much redundancy, as much versatility as you possibly can so that there’s not any one or two bad events that can sabotage your entire season. So we don’t go into 2016 assuming all of our players are going to stay healthy, assuming we’re going to have healthy starting pitching, you almost have to go in assuming someone is going to go down, assuming there’s gonna be a freak injury, assuming someone’s going to fade away.”

When put like that, it becomes clearer and clearer that this winter won’t be focused on just one name. It’s very possible the Cubs go after a big name—and even succeed in acquiring one—but their goal isn’t to just add an ace and call it a postseason. They’ve identified their weaknesses and they plan to address them, but they will also reinforce their strengths. They realize that it’s not just about filling current holes, it’s about doing your best to make sure others don’t spring up during the grind of a long summer.

“We’re all on the same page as an organization,” Epstein said. “Our goals are clear, our priorities are clear. I don’t have any worry that having accomplished so much this year, our players—and our young players—will show up complacent at all next year or taking things for granted or thinking they’re going to sort of walk their way through the regular season then sprint towards the postseason, because baseball doesn’t operate that way. I think the opposite is true and I sense this from looking at their eyes [Wednesday] as they watched the Mets celebrate and then seeing their feelings in the clubhouse after we were done playing; they’re going to come back extremely hungry and extremely focused, and in great shape and ready to take this to the next level. I really wish Opening Day were next week.”

When Epstein puts it like that, I think we can all agree that we’d love to fast-forward through this winter and get 2016 going in earnest. But that would mean we’d miss an offseason sure to be packed with action on the North Side of town. It really can’t be understated, and it shouldn’t be taken as hyperbole: this is a winter that could bring this team onto the precipice of greatness. The Cubs aren’t content with being good, they want to create a team no one will ever forget. It’s time to get back to work.

Lead photo courtesy of Jeff Curry-USA TODAY Sports