Moneyball, The Big Short, And The Ultimate Bait-And-Switch

Moneyball is one of the five most important baseball books ever written, and given its easily absorbed central premise, it’s often used as a verb to describe building a baseball team on the cheap. In that sense, would be easy to look at the last three years and say Red Sox are Moneyballing. Judging from their words and their actions, they plainly think they’re on to something that other teams aren’t — and it’s about how they do or do not spend money, far more on the “do not spend money side.”

In principle this can work well enough, and the Sox plainly think it will. Zigging when everyone else zags can be good, but you run the risk of this:

Suffice to say, the jury’s still out on this whole... experiment. There’s still a long time until Spring Training starts, provided you consider two months a long time, for the team to put together its full roster of castoffs and aging stars (hello, Justin Turner!) and prove us wrong.

But if we say the Sox are Moneyballing it, we’re already off the mark. It wouldn’t even be the most appropriate Michael Lewis book to cite for this particular moment. Right now the Sox are acting far more like the iconoclast investors central to The Big Short, the ones who profited big when the markets went bust, than they are like Billy Beane, who’s merely out there proving all his critics right 20 years later.

Just as the central figures in The Big Short bet against the housing market, the Sox are betting against the market regulating premium player contracts in Major League Baseball. Without any other plausible explanation, it increasingly looks like the Sox are expecting the league’s financial model to implode around them at around the exact point their hard work in building a bottom-up organization reaches maturity and makes them World Series contenders for years, and that we are to support them in advance of this achievement. They want the sport to go to absolute shit, then take it over.

We are being asked to prove a negative, more or less. Whereas The Big Short’s protagonists had reams of hard-to-find data to support their claims, we have vibes, and the vibes are “money is a contstruct, maaaaan.” While I strongly recommend ignoring any meaning in Sam Kennedy’s comments at any time, I believed him when he said “I would put our organization and our track record against anybody else’s in baseball, period.” To be clear, I’m sure he would put the Sox’s moves up against anyone’s. It’s just that when you’re that certain about something so obviously subjective, it’s an obvious tell that you’re overcompensating.

What he’s doing, and what management has done, has pulled an incredible bait-and-switch on Sox fans over 20 years. The Red Sox won four World Series from 2004-2018 by trying their hardest. Now, they’ve plainly stopped doing so, and they’re leaning on the times they did try to justify their current approach. “If we won four World Series, how stupid could we be?” they ask, more or less. The answer is: Not at all. Which is why they know, as we know, that the justifications for this rebuild are pure public relations.

It is worth repeating forever and ever that the 2018 Red Sox were not just a great team that won the World Series. They were a historically great team with a young core, which the Sox traded in, three years for this. There is nothing about a rebuild that is inherently right or wrong, but when it comes at the cost of dismantling the best team in franchise history, the bar is set far higher than it would be coming off a last-place season — i.e., I’d understand if they were just starting now, coming off a last-place finish in which the bloated contracts of Mookie Betts and Chris Sale sink the team, but the timing was all wrong from the start.

The reason that the the comparison to The Big Short isn’t perfect is the same as why the Sox’s approach has been awful: The market is plainly not going to burst. The Sox are acting like the smartest guys in the room by creating a losing product in a closed system that rewards good teams. All they’re doing is trying to get back to where they were and voluntarily bailed on, but they’re taking side roads instead of the highway and they packed sandwiches instead of stopping at McD’s. And they’re doing this during a race that never stops.

If they’re plainly wrong, it’s for one reason: In any given year, a team on a shorter boom-and-bust scale will be more willing to go all-in for a title than the financially prudent-above-all-else team, which will lead to the Sox never, likely, ending up as title favorites. I prefer the former approach, because it won the Sox four World Series titles, but, sadly, that’s no longer how they want to butter their bread.

Let them fill up on it. It’s empty calories. Let them feel superior — you can’t stop it anyway. The fact is that when they actually want to win they’re going to have to spend money, or their chance to win will be weakened, and we’ll end up right back here with nothing to show for it instead of a banner. They traded pay-to-play for a roll of the dice. I don’t feel lucky.