Red Sox President Dave Dombrowski’s major moves last season — signing David Price to the largest contract ever given to a starting pitcher and bringing in all-world closer Craig Kimbrel for a bounty of minor league prospects — were about winning now as much as winning later. After all, Kimbrel isn’t just all-world, he’s all-world signed for three seasons. Price wasn’t just the best starter available, he was the best starter available signed for three years (with maybe four more depending on his opt-out). Those two guys were going to be in Boston for the near term along with Mookie Betts, Xander Bogaerts, Jackie Bradley, at least one of the Red Sox’s young catchers and Dustin Pedroia. But that wasn’t all. The team had a long-term plan with Andrew Benintendi, Yoan Moncada, Michael Kopech, Rafael Devers, and a host of other youngsters on the way to Boston over the next half decade. The Red Sox could win now and later as the next wave was on the way to take the handoff. The Red Sox were set to dominate the American League over the next decade in a way not seen since the late-90s/early-aughts Yankee teams.

But long term isn’t Dave Dombrowski’s modus operandi, and in the end he couldn’t help himself. He saw the shiny toy dangled in front of him in Chris Sale, and he grabbed it. This isn’t to take anything away from Sale. He’s fantastic. He’ll probably be wonderful in Boston. But the Red Sox didn’t need him. They already had a very good rotation. In fact, it wasn’t difficult to squint and see the 2017 rotation ending up better than the 2016 rotation. Sure, Porcello takes a reasonable step back, but it’s offset by Price’s improvement. The Red Sox get a good season out of Eduardo Rodriguez, Drew Pomeranz is then a number three starter cast as the number four starter (and if he pitches more like the San Diego version of Pomeranz he’s a number two), and then the Red Sox have Steven Wright and Clay Buchholz to hold down the number five spot. That’s a very good rotation. Put that in front of the league’s leading offense (or something reasonably close to that) and watch the wins roll in. Chris Sale is fantastic, but the marginal value added by bringing him to Boston isn’t great.

But Dave Dombrowski doesn’t do marginal value. He likes good players. He likes big names. Chris Sale is a good player. He’s a big name. He’ll look beautiful on a ticket stub. But the Red Sox really didn’t need him in 2017. They didn’t need him in 2018 either, with Price, Porcello, Rodriguez, Pomeranz, and Wright all under team control. Heck, all those guys with the lone exception of Pomeranz are under contract in 2019, too.

Perhaps the craziest part of all this is that most everything went right for the Red Sox in 2016. There was nothing forcing or even pointing the front office in the direction of making a big change. Price was good, Betts was incredible, Bogaerts was very good, David Ortiz was one of the best hitters in baseball, and the Red Sox got helping hands from two of the three guys who helped tank the 2015 season in Porcello and Hanley Ramirez (Pablo Sandoval, for better or worse, missed the season due to injury). It was speculated the Red Sox would try to dump Ramirez’s remaining three years on someone else, but they didn’t, and Hanley dedicated himself in the off-season and had a hell of a year. He became a serviceable defensive first baseman, something anyone who watched him in left field last season wouldn’t have thought possible, and he mashed at the plate. Suddenly the next two seasons of his deal look like a good thing instead of a disaster. Porcello’s turnaround was even more impressive. He won the damn Cy Young award after being below average in 2015. You could have made an incredible amount of money, maybe more than Rick Porcello’s contract, betting on that. I’m not convinced he’ll be that good again in 2017, but even a lesser version of 2016 Rick Porcello would be fantastic, and it fits even more so if Price’s runs allowed fall more in line with his peripheral stats. What do you need to add to all that? A reliever maybe. A few long-term deals for young stars.

The Red Sox are coming off 93 wins and a division title, and possess a young team headed into their prime and an amazing farm system set to bear fruit through the next decade. It all looked bright, so, so bright. This is THE set up. It’s what front offices strive to have. This is Theo’s wet dream.

This is why I can’t shake the oddness of the Sale deal. What’s the difference between what Sale brings and what the pitcher he bumps out of the rotation brings? Two wins? Three? You might argue more than that by saying, ‘Well what if Buchholz is just awful?” or “What if Wright is still hurt or can’t regain his first half of 2016 form?” and those are both reasonable questions individually, but here’s the thing. The Red Sox have both those guys! So the answer to the first question is move Buchholz and his one-year deal out of the rotation and put Wright in. The answer to the second question is move Wright out of the rotation and put Buchholz in. Point is, the floor for the fifth spot in the rotation was pretty high, say one-to-three wins above replacement. Removing those guys for Sale by trading your two best prospects (and two other valuable prospects as well) is an extreme move, and severely alters the long term plan and the farm system’s ability to supplement the major league team.

One of the main reasons the Red Sox paid David Price over $200 million was so they wouldn’t have to make a farm system destroying deal like this.

The other aspect of this that bothers me even more is this: one of the main reasons the Red Sox paid David Price over $200 million was so they wouldn’t have to make a farm system destroying deal like this. Recall last off-season when Dombrowski decided he had to have an “ace” (the irony being the eventual 2016 Cy Young award winner was already on his staff) but determined the pitchers on the trade market (including Sale) were too expensive in terms of prospects. So instead he issued the largest contract ever given to a starting pitcher. And now, one year later, now with “Cy” Porcello and Pomeranz, he blows up the farm system anyway. Does this seem like the workings of someone with a plan, or the meanderings of a ten-year-old in a mall whose parents just gave him a $20 bill and told him to “have fun?”

You don’t even have to go back to Price’s contract, though, because come to think of it, it’s also why the Sox dealt their best pitching prospect in Anderson Espinoza for Pomeranz at the deadline (and then didn’t rescind the deal when they had the chance after the Padres medical shenanigans were revealed). The Red Sox said they needed a starter (they did) and got the biggest name available at least in part because they liked that he was under contract for two more seasons beyond 2016. And then, after those two deals, they blew the hell out of the farm system for Chris Sale anyway. Oof.

That’s really the problem with many of these Dombrowski trades and signings. They’re fine in a vacuum, devoid of context. Is Chris Sale worth Yoan Moncada, Michael Kopech and Luis Alexander Basabe? Yes. Is he worth it to a team that just paid David Price $200 million and traded Espinoza for Pomeranz? That’s a much different question. Is David Price worth $200+ million and an opt-out? He can be if spending that money gets you value on the field, fills out the rotation, and prevents you from deconstructing the farm system. Part of the reason to pay Price and accept the pain of losing Espinoza for Pomeranz is to hold on to players like Kopech, Basabe, and Moncada because they could be valuable major leaguers one day, but also because they could be used to acquire major leaguers the team actually needs further down the line.

So here we are with a 2017 Red Sox team better on paper than their 2016 counterparts, but really, if we’re being truthful, only marginally so, and now the team’s farm system has gone from one of the best in the game to one of the worst. The object isn’t to collect shiny prospects, so that in and of itself hardly matters. What does matter is the long term plan, and Dombrowski’s long term plan seems to be win now and who cares if everything becomes completely unsustainable and falls apart after that.

Dombrowski has put everything on the next two-to-three seasons and after that, the piper will be waiting. It didn’t have to be that way.

The argument for all of this is that the front office’s goal is to win a World Series, and that’s what Dombrowski is trying to do. But actually, that’s not really the goal. The goal is really to win lots of World Series, to be a dynasty, to be in position to win every year. That is admittedly incredibly difficult. With free agency, the crapshoot that is the draft, the rollercoaster of player development, injuries, and all the other aspects that go into creating a roster for the long term, in the end it’s much easier to just load up and go for it now, right now, and worry about tomorrow tomorrow. That’s what the Red Sox have done.

Bizarrely, though, they were on the precipice of being a World Series contender for the next half-decade. They didn’t need to go all in. The major league roster was, with a few tweaks, set. They had done the hard part! They were already there. They didn’t need to liquidate the farm for one win-now player. But they did and now, instead of long term success, there is turnover ahead. The team has no choice. Dombrowski has put everything on the next two-to-three seasons and after that, the piper will be waiting. It didn’t have to be that way. Indeed it could have been a whole lot better, a whole lot more fulfilling, and a whole lot more fun. But now it’s the next few seasons and (not or) bust. And that’s why the Sale deal was a bad idea. Winning now isn’t the hard part. Winning in perpetuity is. It’s a shame Dave Dombrowski never realized that.

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