What is next for the Red Sox?

The most famous story about Red Sox owner John Henry had nothing to do with breaking the curse, but instead about hiring Billy Beane, the famous last-scene-in-Moneyball that was framed, at the time, as a little-guy-over-big-guy story of the small-market Athletics general manager spurning the big-money Sox because Beane claimed he would never make another choice based on money again.

That’s certainly one way to interpret it. Another way is that he, and Michael Lewis, had it completely backwards, one of the Original Sins of sabermetrics itself. It wasn’t that analytics were making the Athletics more even with the Red Sox, nor was it that Boston wanted to truly combine big money with big data; no, they actually desired to be the Athletics.

By any back-of-the-napkin estimate, Beane was creating what could be considered hundreds of millions in surplus value for Oakland, and it would only be amplified in Boston. Imagine the Red Sox, the Red Sox, winning a World Series with a sub-$100 million payroll, is I’m sure what Henry was really thinking. And in a way, he was always chasing that dragon despite Boston’s immense success in the 21st century.

That doesn’t mean Henry didn’t have a proclivity to spend; no, the contracts for Chris Sale, David Price, and further down the road... Hanley Ramirez, Pablo Sandoval, Carl Crawford, and (you get it!) others show this wasn’t some hard and fast rule.

I think he was always of two minds when he hired Theo Epstein and especially Ben Cherington, that there was a need to spend to keep pace with the Yankees and the American League generally, and an innate desire to develop cheap talent and sign bargain deals to win. Case in point, the 2013 World Series winners featured the likes of Stephen Drew, Jonny Gomes, Mike Napoli, Daniel Nava, Jake Peavy, and Ryan Dempster, all players most mid-market teams could even muster.

That’s what makes this current pivot a bit odd. Yes, the team has spent a lot of money on players like Sale and Price, and they hired Dave Dombrowski to do essentially that, but they also have a historic Championship under their belt, with two in the decade and four in the century. Since the curse, the team’s valuation has jumped nearly six-fold, and their revenue has more than doubled.

The logical next step, then, if your plan is to get under the luxury tax, is certainly not to continue with Dombrowski, which paved the way for new president of baseball operations, Chaim Bloom. Bloom was a Senior VP of baseball operations at the Rays, which again, makes all the sense in the world when you consider what the Red Sox plan to do.

Taking a quick look at Cot’s, which now thankfully includes arbitration estimates, Boston has approximately $220 million committed to next year in taxed dollars, putting them about $12.9 million over the tax threshold, where they have been over for the last two years. Now, CEO Sam Kennedy has said that the threshold is a “guide post” and not a “a hard and fast mandate,” but you guarantee you don’t bring in a Rays executive if your plan is to ignore it.

That leaves them, to frankly understate it, in a very precarious position. The only players who could conceivably be moved in a trade are JD Martinez, who recently opted back into his contract, Mookie Betts, who has one year and likely ~$27 million left on his team control, and Jackie Bradley Jr., who is likely to be paid around $11 million.

Trading Martinez or Betts is the best way to stay under the threshold, though they could trade Bradley and a couple of other arbitration-eligible to scrape under, but that would leave them with little room for improvements throughout the season.

Let’s say they move Betts, for example. That would give them about $14 million in cap space, or if they move Martinez, about $9 million. That would leave them with barely enough room to sign a pitcher—losing Rick Porcello to free agency makes this a priority—and that could conceivably allow them to sign, say, Kyle Gibson, Michael Pineda, Rich Hill (there’s a history), Cole Hamels, or re-sign Porcello.

That’s essentially one step forward, and two steps back. Signing Gibson, for example, probably puts them a win better than having Porcello alone, but they’re a good six wins in the hole if Betts heads out. For a team that couldn’t even crack 85 wins in 2019, that leaves a host of questions if they continue to backslide because of missing Betts , possibly even triggering a full-scale rebuild or retool.

They could limit the damage in moving Martinez, but that forces them to essentially make trades, or stay relatively stagnant in free agency, maybe signing a reliever like Pedro Strop or Dellin Betances on a one-year deal. But with essentially a wide-open hole in the infield with Dustin Pedroia as a total question mark, no first baseman, no real fourth outfielder if Martinez is not needed in the field or traded, and a very weak relieving core, the questions remain and the solutions are dwindling.

With the farm system as weak as it is, it may behoove them to move Betts even if the CBT wasn’t an issue; it’s possible they find themselves too weak to make the playoffs with him, thus making him more useful without. I would probably say it’s better to wait to mid-year to determine that, because then that would put quite a few players on the table.

It’s an understatement to say this team is at a crossroads. With their best player in decades at the end of team control, the obvious move is to just extend him and deal with the consequences later. But with the figment of a Beane-like regime dancing around Henry’s head, he sees another path—reloading the farm system quickly a la the Yankees in 2016, turning around the farm system while still retaining the likes of Sale, Andrew Benintendi, and Rafael Devers, and putting themselves in a very good position come 2021.

Yet if they flop the possible retool, they find themselves with a lower operating revenue, lower than if they just bit the bullet and kept Betts and made their possible postseason revenue. This is the current debate of our time in baseball, and the Red Sox are currently on the front lines.