Take Me To Your Leader: Theo Epstein and the Inimitable Inevitability of the Cubs’ Success

If imitation truly is the highest form of flattery, the Cubs are being roundly fêted by the roundly fetid bottom-dwellers across Major League Baseball. One could argue, in fact, that at least a portion of the team’s rampant success of late has been due to the rampant suckiness of the Reds and Brewers, among others.

Professional sports has long been a copycat enterprise in which various organizations seek to decipher blueprints laid out by other architects, to climb up and stand on the shoulders of San Francisco Giants. But it’s not as simple as just inserting Tab A into Slot B and tanking for high draft picks. Those who assume organizational development is but a cookie-cutter process are doomed to end up as the subject of a Pinterest-fail listicle.

As far as other teams copying the Cubs’ model, the image that comes to mind for me is that of a little boy lathering up with shaving cream and mimicking his dad. It’s cute an all, just not much actually getting done sans blade or beard. So it is with all the would-be contenders who’re trying to rebuild from scratch on shoestring budgets. Problem is, they all lack one important factor: Theo Epstein, the greatest leader in the whole wide world.

While there’s no shortage of click-baity hyperbole in the proclamation of Epstein’s esteem, there’s something to be said for the process over which he’s presided these last few years. And it’s so much more than that too, a philosophy that has developed organically with age and experience.

“I don’t know how to lead,” Epstein told The Athletic’s Jon Greenberg. “I know how to be myself. I think I know the components that go into a healthy baseball operation, so I can lead that. But I don’t know if I can lead a lemonade stand.

“To me, the more you talk about leadership, the less you have any chance of being a leader.”

The key to Epstein’s success has been about knowing who is and knowing how to surround himself with the right people. Rather than a bunch of yes-men who will compliment him, he has built up a roster of fellow execs — Jed Hoyer, Jason McLeod, et. al — who complement him.

“Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don’t like,” the Cubs’ baseball boss explained to David Axelrod on his Axe Files podcast in January. “So if you can ask them or figure out what that 20 percent is, and figure out a way to do it for them, you’ll make them really happy, improve their quality of life and their work experience. If you do a good job with it, they’ll start to give you more and more responsibility.”

Amid the growing trend toward statistical analysis in sports, baseball in particular, there’s this fallacious idea that stats and scouts are an either/or subject. To think that anything is so binary as to be distilled into right or wrong and better or worse is to deny fundamental aspects of the game. It is, after all, being played by human beings whose performance is illustrated by numbers. Metrics can’t measure personality just as prioritizing grit might overvalue a guy with a .300 wOBA.

Epstein understands this, is acutely aware of the bigger picture. While others are trying to copy what they believe is a paint-by-numbers strategy, he’s leading members of the Cubs brass as they lie on their backs and touch up the ceiling of the Sistine Chapel. Or maybe they’re using spray paint to tag a mural somewhere in Chicago. The one thing they haven’t painted is themselves into a corner.

To take nothing away from any of the other members of what is undoubtedly a powerful collective, the general precepts that govern the goings-on in Cubdom come from the president. There’s much more about that in Patrick Mooney’s recent piece over at CSN Chicago, but the following excerpt sums things up quite nicely.

Epstein always understands his audience — whether it’s professional athletes, Democratic donors, Cubs Convention diehards or the pesky media — and knows how to deliver a one-liner with perfect timing.

Epstein loves baseball, but he’s not some poet or romantic, dropping F-bombs at the right moment and calling BS when he sees it. Of course, Epstein has a huge ego. There’s no other way to end 194 combined years of curses between the Cubs and his hometown Boston Red Sox. But Epstein also didn’t crash all the late-night talk shows this offseason or cash in with a quick book on leadership skills and management philosophy/fluff.

This has all been a long-winded way of saying that you’ve got to have the right team in place if you’re going to undertake a rebuild. And that’s not even talking about the roster. The gross oversimplification of the effort required to completely overhaul a franchise that has been presented in the media is laughable and, to be honest, insulting. It’s as though engineering a turnaround is as simple as the Underpants Gnomes’ financial model.

  1. Collect draft picks
  2. ?
  3. Win

Yeah, um, that’s cool and everything, but it doesn’t work that way. It’s absolutely true that the Cubs were able to hoard high draft picks as the result of a conscious effort to limit the competitiveness of the team on the field. It’s true that they didn’t carry a payroll commensurate with their major-market status, though the extent to which they could have spent in the early Ricketts years was likely governed by the debt they leveraged and the nature of their purchase of the team.

And, for what it’s worth, the payroll in those lean years wasn’t as low as what you might be thinking.

But to reason that turning the Cubs into world champions was as simple as converting draft picks to superstars is no different from a medieval alchemist believing he could turn lead to gold. There’s no magic bullet, no potion you can drink, that turns the whole thing around. Do you realize how much had to go right in order for things to happen the way they did? Top picks exceeded expectation, (most) trades worked out in the Cubs’ favor, unheralded prospects developed into studs.

To be fair, much of that happened as a result of Epstein and Co.’s diligence. They didn’t fall bass-ackwards into all these players, though there were hefty doses of luck involved. Kris Bryant could easily be smashing home runs into the Crawford Boxes in Houston, and had the White Sox gone a different direction in 2014, the Cubs would have had Carlos Rodon instead of Kyle Schwarber. And what if the Rangers had been smart enough to not give up all kinds of prospects for Matt Garza and Ryan Dempster?

My point in all this is that, while Epstein’s pedigree and process all but ensured success on some level, what the Cubs have done over the last five years can’t be repeated. Not even in a vacuum and probably not even were they to travel back in time and start over with the same exact parameters. Their accomplishments are as inimitable as they were inevitable.

Which is why it does us no good to look back and wonder what would have happened if a pick had been made differently or if the Cubs had lost Game 7. “What if” is a foolish and hollow question, rendered inert by the answer of what is. The difference on paper is a single letter, but we know that life doesn’t happen on paper. Nor does baseball. Epstein knows that perhaps better than anyone else in the game, save for those with whom he’s surrounded himself.

So don’t worry when long stretches of the season lead to highway hypnosis that has you needing to take a nap or two. The man at the wheel knows where he’s going and you need only enjoy the ride.

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