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Dombrowski’s Best and Worst Moves with the Red Sox

Let’s take a look at some of Dave Dombrowksi’s most notable decisions in his time as Boston’s President of Baseball Operations.

Red Sox President of Baseball Operations David Dombrowski by Arturo Pardavila III is licensed under CC BY 2.0

Dombrowski’s Best and Worst Moves with the Red Sox

Estimated Reading Time: 5 Minutes

Last week, the Boston Red Sox fired Dave Dombrowski. His tenure as the President of Baseball Operations came to a controversial close, which is perhaps the most fitting way his career with the Sox could have ended. 

Dombrowski’s time in Boston was full of ups and downs, a perpetual see-saw of praise and criticisms (mostly the latter if you live in Boston). His team won three straight division titles. But he depleted the farm system. He built a championship roster in 2018. But he always overlooked building a bullpen. For every positive with Dombrowski, there almost always seems to be a “yeah, but…” to follow.

So with his reign in Boston now over, let’s break down some of Dombrowski’s most notable personnel moves over the years.

The Good

The trades for Craig Kimbrel and Chris Sale – Some may say that it doesn’t take much skill as a GM to trade away big pieces for star players. And to a degree, that is true. There is little craftiness involved in trading 4 prospects for Kimbrel and another 4 for Sale. It just comes down to the willingness to mortgage part of the future for the present. And since it worked (Kimbrel and Sale played sizable roles for Boston in their 2018 championship run) I think it’s fair to say that these were good moves.

Kimbrel (now with the Chicago cubs) managed to stay relatively healthy in his three seasons with Boston, earning at least 30 saves in each while averaging a 2.44 ERA. He also recorded 6 saves in the postseason. Sale earned All-Star nods in his first two season with Boston, going 29-12 in those years with a sub-3.00 ERA. (His numbers this year were far worse before his season was derailed by injuries, but more on that later).

As of now, the only real blue-chip prospects Dombroskwi gave up in these trades were outfielder Manuel Margot (San Diego) and infielder Yoan Moncada (Chicago White Sox). The other 6 have combined for little to no Major League experience as of yet, so time will ultimately tell. But if it looks like giving up Moncada and Margot got them Sale and Kimbrel on the way to a title, then consider them good moves- even if they might have been easy decisions to make.

The mid-season acquisitions of Nathan Eovaldi and Steve Pearce in 2018 – Now THESE are the kinds of moves that a GM can brag about. Bringing in the right guys at the right time (sometimes off the proverbial scrap-heap) to fill much-needed roles.

And in the middle of 2018, an otherwise loaded lineup for Boston showed two major weaknesses: a versatile arm to add to the rotation, and a right-handed bat with some pop. At the trade deadline, Dombrowski sent prospect Jalen Beeks to Tampa Bay in exchange for Nathan Eovaldi. Four days later, he sent prospect Santiago Espinal to Toronto for Steve Pearce.

Eovaldi would go on to not only start games for Boston down the stretch and in the postseason, but pitch meaningful innings in relief as well (how could we forget Game 3 of the World Series?). Pearce, a journeyman who has now played for every team in the A.L. East, has to take the cake as the most surprising World Series MVP in recent memory. No championship team is complete without a perfectly-designed supporting cast. Eovaldi and Pearce rounded out a stellar 2018 roster for Boston, much to Dombrowski’s credit.

The Bad

The latest contracts for Sale and Eovaldi – Dombrowski did well to bring these two into the fold via trade. But the contracts he gave out to these two in 2019 were far from ideal.

In the case of Eovaldi, this was the classic overpayment. Sure, Eovaldi was tough as nails in the playoffs and a great piece to retain on your pitching staff. Few people would argue that Boston should have let him walk in the offseason. But is he worth nearly $68 million over 4 years? His $17 million AAV puts him in the ballpark of guys like Jose Abreu, Corey Kluber, and Mike Trout. It’s just too much money for a guy who gave you an (albeit stellar) half a season. To make matters worse, Eovaldi missed most of 2019 with injuries.

The case of Sale is a bit different, and much more frustrating as a fan. As previously described, Sale was excellent in his first two seasons in Boston. So when Dombrowski extended him with a 5-year, $145 million, the money seemed about right. But the timing made no sense, and in retrospect appears even worse. Why? Because Sale had a full season left on his original contract. And his only issue in his time with Boston to that point was his ability to stay on the field, which was clear late in 2018. There was no pressing reason to sign him to an extension before the end of this current season. But Dombrowski did, and Sale went on to pitch poorly in 2019 before being shut down in August due to elbow injuries.

The trades for Tyler Thornburg and Carson Smith – It’s easy to group these two moves together, since they tell such similar stories. Dombrowski wanted to bolster the bullpen in both cases, and in both cases he traded away sizable pieces for guys with persistent injury problems.

Thornburg was acquired from Milwaukee in 2016 for Travis Shaw and three prospects. He would start 2017 on the disabled list before ultimately missing the entire season with a shoulder injury. He was released from Boston in July 2019, after throwing less than 50 total innings at the Major League level in 3 years.

Smith was acquired in 2015 (along with Roenis Elias) in exchange for Wade Miley and a prospect. Like Thornburg, Smith was diagnosed with an injury (flexor muscle strain) before ever taking the field in the regular season. He would go on to pitch in 3 games in 2016, before needing Tommy John surgery. He would pitch only 20 more innings over the next two seasons for Boston (mostly due to a self-inflicted shoulder injury 2018), and was released in June 2019 after not appearing in a single game this season.

Ryan Kelly lives in Cambridge, MA, a stone's throw away from his beloved Boston teams. When he is not working as an editorial assistant, he is providing commentary on the Boston Red Sox and Boston Bruins for The Turf.

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