How the Cubs Plan to Win in 2019: Trade for Kris Bryant and Implement Philosophical Changes

There’s no such thing as a sure thing in baseball. So whether they blow through luxury tax penalties to sign Bryce Harper or shed waterlogged contracts to save as much money as possible, the Cubs will bear a significant measure of risk heading into 2019. And while I’m of the mind that they should spend, everything I’ve been told is that they won’t do so to the extent many want them to.

Not that their financial proclivities are anything new at this point, it’s just good to set the context for what we’re going to be talking about. And what we’ve been talking about to this point is what Theo Epstein means when he talks about organizational philosophy and how that translates to the Cubs’ willingness to change what they’ve done and perhaps even who they are.

So far, the questions outnumber the answers. How could Epstein be pissed off about a 95-win season? If it’s widely believed that Joe Maddon just did his best job as manager, how is he not getting an extension? Could Kris Bryant really be traded and, if not, why don’t the Cubs say he’s not moving? What exactly is involved in re-creating a sense of urgency and are all these changes just a matter of placating young players?

Some of those can only be answered over time and most are imbued with enough nuance that the resultant discussion devolves into a battle of semantics that sees opposing sides climbing atop their respective hills. There are, however, some reasonable conclusions to be drawn based on what Epstein and others have said and just plain ol’ common sense.

Perhaps the easiest to address is the idea that the Cubs could trade Bryant this winter, a conclusion drawn by Buster Olney based on what he had heard from league sources. Olney has continued to defend his position adamantly, with strenuous support from Jesse Rogers, who provided his ESPN colleague the quote from Epstein about how the Cubs have “never operated with untouchables.” And while I don’t agree with the stance they’ve adopted, I have come to better understand why they’ve adopted it.

This is one of those matters of semantics. I have no doubt Olney has heard that the Cubs are willing to listen to offers on Bryant and that the likelihood of him being traded is greater now than it was in the past. But that’s like saying I’m older today than I was yesterday. Given his potential production with what will still be a relatively low salary, not to mention the reduced value due to his shoulder injury, it would be nearly impossible for the Cubs to get back anything close to an adequate return.

And that’s the only thing you really need to know, regardless of what other noise is out there. Epstein will make any move he can if it gives the Cubs a better chance to win, but is there really such a move involving Bryant that makes sense? No, at least not now. Rather, the Cubs are viewing this almost like trading for Bryant without having to give up anything in return.

Given all that happened — or didn’t — post-shoulder injury, it’s easy to forget just how good Bryant was through mid-May. Extrapolate that early production through the whole season and you’re talking about a player who’s once again worth close to 7 fWAR instead of the 2.3 he posted. Having Bryant back at full health effectively adds a top-tier free agent to the roster and gives the entire lineup a big boost.

As for the next two seasons, though, that’s where we could really see more of a shift and it’s why I’ve been so perturbed by the location at which Olney planted his flag. If Bryant continues to rebuff the Cubs’ efforts to extend him beyond his rookie deal, the possibility of a trade becomes that much more realistic because they don’t want to end up with nothing to show for his time in Chicago but a compensatory draft pick.

But we’re also talking about a time at which they’ll be operating under a new CBA with a fully realized broadcast media deal and, ideally, more positive cash flow from the Ricketts family’s Wrigleyville investments. Which is to say the Cubs could throw money at Bryant that they’re reportedly unwilling to give to Manny Machado or Bryce Harper. That bridge is a ways off, though, so let’s take a shorter walk.

Epstein spoke in his postmortem presser about a need to be more on-mission every day and to get back to more of the attitude and performance of two years ago. We’ve already seen at least one coaching change as a means by which to make that happen, and there could be another in the offing. And while that speaks volumes of what the team thought about the jobs performed by the men in those roles, it’s also reflective of an overall philosophical shift.

While the Cubs aren’t trying to completely scrap Joe Maddon’s laid-back tendencies and constant lineup tinkering, they do appear to be establishing tighter parameters within which he can operate. Sahadev Sharma has an excellent piece in The Athletic (subscription) about the amoeba lineups and how or why they could become more static next season. Bryant being healthy could be the gelatin that solidifies things to a great extent.

Much more than the idea that they’ll shift to a more traditional model, the front office’s plan appears to hinge on the very simple concept of being more intentional with their communication. I can’t speak to what’s been said on the inside over the last season or three, but it seems they’ve been operating with a bit too much comfort in an implicit understanding of the way things are and will be.

So rather than being very clear and up-front about Maddon’s quirks, it’s been taken for granted that things are going to be in a constant state of flux. And while that adds a certain measure of excitement and keeps things fresh, you run the risk if creating change fatigue and allowing uncertainty to become anxiety. Again, some of that is inevitable with a roster filled with guys who could all be everyday players. The key, then, is to mitigate as much unnecessary friction as possible.

As for the conflicting rationale between the job Maddon has done and the job he will do, well, it’s all derived from his ability to alleviate those issues while accepting and fostering some of the necessary changes. We’re not talking about anything seismic here, just some tweaks that become necessary as a group shifts and grows with time. You can’t always motivate and manage the same way, so Maddon showing that he’s embracing what the Cubs are looking for likely earns him a new deal.

And therein lies the paradox of this whole thing. The Cubs have great talent but it failed them in critical moments. They have great wealth but don’t seem to want to spend it. They won more games than in the previous season but are more disappointed in their results. The difference between success and failure is but an eyelash, which is why everyone’s splitting hairs about what the Cubs need to do and why.

They’ll be active this winter, though that probably means creating a bunch of little ripples instead of one or two big splashes. And that’s in keeping with what Epstein and Jed Hoyer have been saying for some time, which is that a few tweaks could yield appreciable results. Feel free to nod your heads or shake your fists with as much vehemence as you deem necessary when it comes to your response to that strategy.

Just know that you’ll be shaking or nodding for a while, since the effectiveness of this philosophical change can’t be determined for another year or so. And who knows, maybe the new $5.1 billion broadcast rights deal MLB just secured with FOX Sports — or the $300 million steaming deal with DAZN — will change the calculus and rhetoric a little bit. Now can we please get some activity in the hot stove?