Thoughts On Dave Dombrowski's Red Sox Legacy

Now that ol' Double D has a new gig, l've been thinking about his time in Boston...

Photo: Arturo Pardavila III

A few days ago, the Philadelphia Phillies announced Dave Dombrowski as their new General Manager.

It was a strange hire for a few reasons, mostly having to do with the Phillies who aren’t in a position to raise payroll or leverage a farm system for major league talent, the two things which are at least publicly perceived to be Dombrowski’s strengths as an executive. His hiring seems as good a time as any to take stock of the Dombrowski era in Boston, as perhaps that can provide greater clarity as to the Red Sox current situation.

Dombrowski wasn’t in Boston long but he had a profound impact on the franchise beyond what what might be expected, owing mostly to his role constructing the 2018 World Series championship team. Putting together the winningest regular season team in Red Sox history and the first team to beat three 100-win teams on the way to winning the World Series was an achievement and a thing to behold. Looking back on it now, though, feels like an opportunity lost.

Perhaps this is the benefit of having watched three other World Series winning Red Sox teams over the past 15 years talking, so keep that in mind. My brain could be warped by winning (a horrible affliction I wish upon you all). Winning a World Series is a true challenge and the way the 2018 team did it is worthy of remembrance and a place among the great teams of the franchise’s long history, but it feels like the Red Sox were poised to do more than that.

When Dombrowski took over, the team was young, cheap, and promising, and the farm system was brimming with talent. They were primed to compete for a long time, but Dombrowski couldn’t or didn’t want to wait. He leveraged all of it for one (big) shot at winning. He won. Then he was fired.

Dombrowski is known as a shrewd trader, and he definitely made his share while with the Red Sox. He arrived at the end of the 2015 season and made two big trades just months later with the Craig Kimbrel deal and the Carson Smith deal. Both were intended to address what was a league-worst Red Sox bullpen in 2015. The Red Sox pen was much better in 2016, but Smith had nothing to do with it (he threw 2.2 innings before getting hurt). Amazing as he was, Kimbrel was only a small part of the turn around which mostly came about because relievers who were already on the team pitched better, like Koji Uehara, Matt Barnes, Joe Kelly, and Robbie Ross. On a per-inning basis, Kimbrel wasn’t even the best reliever on the Red Sox that season. That honor went to Brad Ziegler who Dombrowski stole from the Diamondbacks for two non-prospects mid-season. Dombrowski’s big moves were flashy and expensive, and there was a turnaround so he got the credit for it, but the actual result didn’t have nearly as much to do with his big moves as holdovers pitching better.

Dombrowski gets a lot of credit for trading the right prospects. He seems to have figured out something that a lot of other front office folks haven’t, namely that most prospects bust, or at least never reach their ceilings. So when people say Dombrowski is good at trading the right prospects, I’m not sure that’s true. I don’t think he has any different or special insight over and above other executives. If you trade a lot of prospects (like Dombrowski did), most of the guys you deal won’t turn into much because most prospects don’t turn into much. Dombrowski big skill is he’s not afraid a prospect he trades might turn into something. It happens sometimes. But mostly it doesn’t happen, and Dombrowski knows that.

He knew that when he traded the Red Sox top pitching prospect, Anderson Espinosa, a top 100 prospect in baseball as a hard throwing and promising starter in A-ball, for starter Drew Pomeranz. He wasn’t afraid Espinosa would reach his high ceiling, because he knew that most 17-year-old starters in A-ball don’t reach the majors, let alone reach their ceiling. Dombrowski turned Espinosa into about 240 good innings of major league pitching in 2016 and ‘17 (and 74 innings of bad pitching in 2018). To date Espinosa hasn’t pitched above A-ball due to repeated injuries.

On a base level you absolutely take that. The question that comes to mind with that move and many others is, if you’re going to trade your best pitching prospect and one of the most widely regarded arms in the minors, is Drew Pomeranz the best you can get for him? Maybe so! Pomeranz was very good for a season and a half as a starter for a starter-starved team, but still, the return seems light. (For the record, it seemed light at the time as well.) This illustrates one complaint, that Dombrowski was maybe a bit too willing to deal away top prospects. Was there a way to get Pomeranz without giving up your best pitching prospect? Maybe, maybe not. I certainly wasn’t in the room, nor was I privy to other conversations GMs had about Pomeranz at the time. There is a pattern though. Dombrowski found a guy he wanted and then he paid the price. The Padres asked for Espinosa and Dombrowski said yes. He’s not a haggler. He’s doesn’t move on if the ask is deemed a bit too high by his farm director.

Dombrowski’s predecessor Ben Cherington would never have traded prospects Manuel Margot, Javy Guerra, and Carlos Asuaje for three seasons of Craig Kimbrel. He just wouldn’t have considered that a trade fitting the long-term interests of the Red Sox. Three very good prospects for a (admittedly great) relief pitcher on a (relatively) big contract wasn’t going to happen. Not only did Dombrowski make that exact trade, but he tossed in another prospect, Logan Allen, as well. Allen later was a top-100 prospect himself.

This same outline was followed again and again in the trades for Addison Reed, Eduardo Nunez, Chris Sale, and Tyler Thornburg. All were acquired for multiple minor leaguers, with the exception of Pomeranz for Espinoza. This was a bloodletting for a minor league system that ranked in the top five when Dombrowski took over. The sheer number of minor leagues Dombrowski dealt away was impressive. Two years later Boston’s farm system had gone from the top five to the bottom five in baseball.

That’s not necessarily a demerit for Dombrowski. That’s what farm systems are for. You graduate talent to the majors and you use prospects to acquire major league talent at needed spots to bolster the big club. It was the brute force with which the deals were made that left a bigger hole in the system than normally would’ve been there. The number of trades, the number of prospects per trade, and the talent that went out the door. And again it’s not about whether that talent turned into anything, it’s about what the value of that talent was at the time, and what the loss of that talent meant over the long term.

Dombrowski followed a similar style in free agency. The Red Sox needed a starter so he paid David Price $217 million to fill that hole. They needed a hitter so he paid JD Martinez $110 million to do that. He traded for Chris Sale then gave him a $145 million extension. He gave Xander Bogaerts a $120 million extension. He gave $68 million to Nathan Eovaldi. It’s not that any one of those contracts is bad by itself. It’s the totality of the deals that put Boston in the position where they felt they couldn’t meet Mookie Betts’ asking price. It was the totality of the money that put Boston in the position where they felt they had to use Betts to get out of paying David Price. The Betts deal wasn’t made by Dombrowski, but it was absolutely brought about by his decisions as GM (there is culpability in the owners’ suite as well, to be sure).

Dombrowski was brought in to win and he did win. Boston made the playoffs three out of his four seasons and finished with a winning record every year he was there. The two years before he arrived Boston finished last in the division and the year after he left they finished last again. My question is, without the big trades and expensive flashy free agent signings, where are the Red Sox right now? Could they have won the World Series without Craig Kimbrel, David Price, Chris Sale, and JD Martinez? No. But could they have won with reasonable replacements for those guys? I think it’s definitely possible. Could they have won more games in 2019, 2020, and 2021 with those reasonable replacements and the parts of the farm and major league team that weren’t sold off? I think there’s a good argument.

Dombrowski went full bore toward a championship, damn the torpedoes, damn the farm system, damn the payroll, damn the future, and damn anything else that stood in the way. To his credit he succeeded. But there is a price to pay for that style of team building. It’s not a style that lends itself to long term success. It’s one or two bites at the apple and after that it’s time to pay up.

In 2016, Betts, Bogaerts, and Eduardo Rodriguez were 23 years old. Jackie Bradley was 26. Andrew Benintendi and Rafael Devers were top prospects in baseball. It looked like the start of a long era of Red Sox success was at hand. But that didn’t happen. That is Dave Dombrowski’s Red Sox legacy too.