The Cubs Have Achieved the Ultimate Goal, Now Comes the Hard Part

There’s more than one way to get to Disney World. When my family went with two others a few years ago, we chose to drive while everyone else flew. The Cubs, well, they had to win the World Series to get there. But as everyone who’s been to The Happiest Place on Earth knows, it’s not the getting there that requires the most effort. It’s the staying that keeps you on your toes.

All you’ve got to do to maintain momentum for the trip is to set the cruise and keep gas in the car. Once you’ve reached your destination, however, you find yourself opening up your wallet and shoveling money from it like coal into the gaping maw of a mouse-shaped furnace.

You’ve got multiple parks, dragging kids of different ages along to each place so everyone can enjoy everything. When I went to Disney as a kid, we actually drove over from where we were staying in Tampa and hit both Magic Kingdom and Epcot in the same day before driving back. This most recent visit was done on a six-day park-hopper that allowed plenty of time to try everything more than once, to pick and choose certain attractions in order to maximize the experience.

It’s the same in baseball, where some teams have more of that sparkle-and-fade taste of glory in which they come out of nowhere to win before immediately returning to mediocrity while others remain perpetually in the playoff picture. The difference, or so it seems from my own experience, is having a competent and experienced guide who can set a plan and help the group maximize time and efforts. For our family trip, that was our late friend Ginger, a Disney aficionado who was able to show us the ropes. For the Cubs, that’s obviously Theo Epstein and Jed Hoyer.

You might think bringing home the team’s first World Series in a few years would represent the end of the journey, but that’s not really the case. Well, okay, it sort of is. It’s just that this was never about reaching the peak and then turning around and heading back down the mountain. Rather, it was about moving up from base camp and establishing a permanent outpost at a high enough altitude to allow frequent attempts at the summit.

To do that requires a drastic shift in the way the team views and leverages value, which might sound a bit strange at first. After all, wouldn’t the goal be to acquire as much talent as possible, regardless of the team’s situation? Well, yes, but exactly how, when, and why they acquire it has already changed. Consider that when Epstein and Hoyer first came to town, the goal was to flip short-term, win-now assets for those with more projection and growth opportunity. Now they’re sending Jorge Soler to Kansas City for a year of Wade Davis.

Think of it like the way risk tolerance changes with age when it comes to investments. A younger person can take on much higher risk knowing that the end result will be well worth it, while an older investor needs to move from small and mid caps into blue chips and money markets. That’s an over-simplification, to be sure, but the Cubs have long since left the days of trading a top-of-the-rotation starter for a few prospects behind them.

Now comes the reality of maintaining a competitive product while still finding ways to replenish from within, which means essentially reversing the flow of prospects and win-now players. At the same time, though, it may actually mean taking a few more risks on high-ceiling projects via the draft. You can’t afford to swing and miss when you’re picking at the top, and the Cubs hit big on Kris Bryant and Kyle Schwarber. With a youthful core locked up for the foreseeable future and picks coming much later than before, it’s more possible — necessary, even — to roll the dice.

I suppose that flies in the face of the investment analogy I made earlier, but that’s what happens when you write yourself into a metaphorical mire. It’s also because running a baseball team is different from managing your 401(k). For one, there’s no point at which you get to sit back and say you’re done, you’ve finished the race. And that’s where we get back to the Disney stuff.

When you’re heading there, it’s easy to idealize everything when you picture smiling faces amidst all the magic and wonder. But you quickly realize that leveraging Magic Hours each morning, picking up Fast Passes for various rides (which I think you can do online now), and figuring out how to get the most enjoyment possible for each person is a real chore. And though it might not always seem like it in the moment, having the right guidance ensures that it’s less of a slog and that you can look back and realize what a great experience it was.

Gone are the days when a contract-year commodity like Jake Arrieta would be readily flipped for prospects, but the Cubs can’t keep trading their own controllable assets for rental relievers, either. Going one way or the other would be easy, it’s striking the balance between them that will determine exactly how competitive this team will remain and for how long. I don’t know about you, but I’d be totally fine with the Cubs handling this like me and my daughter riding Expedition Everest five straight times without waiting in line. Yeah, I think we’d all be cool with that.