With the magical championship season of 2018 firmly in the rear view mirror, the disappointment that has been 2019, has put team president, Dave Dombrowski, firmly in the crosshairs as it relates to criticism from Red Sox fans and media alike.

Between the construction of the Red Sox bullpen and a lack of Trade Deadline activity, Dave Dombrowski has garnered enough criticism throughout the season. Perhaps, the biggest criticism of the Red Sox GM has been his handling of the farm system, and his willingness to part with premium prospects, mortgaging the future of the franchise for a “win now” mentality. Looking at the 2018 championship team, it’s impossible to think that the success could have come without Dombrowski’s fingerprints all over the foundation of the team. Free agent signings of David Price and J.D. Martinez, and trade acquisitions Chris Sale and Craig Kimbrel all played key roles throughout the regular season and down the stretch.

As always, there are some trades that can be called into question. The 2018 trade deadline acquisition of Ian Kinsler for pitching prospect Ty Buttrey looks like a bad deal today, as Buttery has blossomed into a solid bullpen arm in Anahiem, while the Red Sox bullpen has lacked stability all season. The Travis Shaw and Mauricio Dubon for Tyler Thornberg deal prior to the start of the 2017 season has generally been lauded as a bad deal from the beginning, and Thornberg’s recent DFA and subsequent release haven’t made the deal look any better. Dombrowski’s willingness to part with then top pitching prospect, Anderson Espinoza, for Drew Pomeranz, in an effort to stabilize the rotation in the summer of 2016, has basically been a wash. Espinoza has battled arm trouble and has had multiple surgeries, while Pomeranz was unable to follow up a solid 2017 season (17-6, 3.32), and was unsigned after a disastrous 2018 season (2-6, 6.08) that saw him lose his spot in the starting rotation.


All Star closer, Craig Kimbrel, was lost to free agency after the 2018 season, the four prospect package that went to San Diego in exchange for his services seems to look like a steal for the Sox, as the end result – a 2018 World Series title- seems worth the price of a barely replacement-level fourth outfielder (Manny Margot), and a back end rotation arm (Logan Allen). The other two prospects involved in the deal don’t project to be major leaguers nearly four years later.

The Blockbuster

The biggest trade that “Dealin’ Dave” was able to pull off to date has been the move to acquire ace pitcher, Chris Sale. The Red Sox came into the Winter Meetings with one of the top starting rotations in the AL, headlined by David Price and reigning AL Cy Young winner, Rick Porcello. Recently acquired, Drew Pomeranz, and highly touted prospect, Eduardo Rodriguez, would slot in behind Price and Porcello, but the need for one more impact starter was deemed a top priority. The Sox also entered those meetings with the consensus #1 farm system in all of baseball. If Dombrowski was determined to leave the meetings with Chris Sale in a Boston uniform, he had the ammunition to do it. Perhaps, what should be Dombrowski’s legacy inside Red Sox Nation (beyond the 2018 World Series), is the decision he made on the prospects going back to Chicago.

The Red Sox had the top two prospects in all of baseball at the time, outfielder, Andrew Benintendi, and infielder, Yoan Moncada. They also boasted a top-15 overall prospect in third baseman, Rafael Devers, and MLB’s fastest rising pitching prospect in flamethrower, Michael Kopech. Chicago’s ask was for four to five prospects all inside the organization’s top 30, with a teams top hitting and top pitching prospect as part of the package. Kopech was certainly to be part of the deal, and the headliner was to come in the form of one of the prospect trio of Benintendi, Devers, and Moncada. The Sox had called up Benintendi for the final few months of the 2016 season, and he was penciled in as the starting left fielder for 2017. His presence as key member of the team for 2017 left him nearly untouchable in trade talks. Likewise, Moncada also had a taste with the big league club in September of 2016, but a poor showing both offensive and defensively, had him back in the minors by season’s end, and his role with the 2017 team had no clear definition. However, the Red Sox had spent heavily on Moncada in the international free agent market, committing a total of $63M for his services in March of 2015. His ability to adjust to pitching in the minor leagues, combined with the raw power and blazing speed, made him an elite prospect, and he projected to be a franchise player. Devers, just 18 years old at the time, was rapidly climbing in the prospect rankings thanks to loud, raw tools. A great feel for the strike zone, and a projectible body that 70 grade power would eventually grow into. Defensively, he was a work in progress, but his work ethic was off the charts, and because of his age the whispers of doubt surrounding his ability to stick at third base were quieted pretty quickly.


For Dombrowski, the decision had to be grueling, but in the end, Yoan Moncada would join Michael Kopech (along with infielder Luis Alexander Basabe, and Victor Diaz) as one of the biggest prospect-for-star trades in MLB history. While the story is still being written, Dombrowski’s decision to hold on to Devers (and Benintendi), in the decision to acquire Chris Sale looks to be one the better moves a front office executive has ever made when pulling off a deal for a star, front line starter. Moncada endured several brutal seasons to start his career for a rebuilding White Sox team, but has come into his own in 2019, hitting .301 with and .893 OPS and 20 HR as the everyday second baseman in Chicago. In Boston, Benintendi has been been the starting left fielder since the beginning of 2017. He grades out as an above average left fielder and has been a 3 WAR player in each of his seasons at the big league level. The key to the entire deal – outside of Sale himself – was the decision to keep Devers, the lower rated rated prospect of the three at the time of deal.

Looking at the numbers that Moncada is putting up in Chicago, especially in an inconsistent season for Sale, would usually bring upon some reflection for the team that traded away that type of talent…until you look at what Rafael Devers has blossomed into himself. In a true breakout season, the young third baseman has been among the best hitters in all of baseball. Posting a .325 batting average with 25 home runs and a .947 OPS to date. He’s inserted himself into the AL MVP conversation, and looks like a franchise cornerstone for years to come.

On Monday night, Chris Sale became the fastest pitcher to 2,000 strikeouts in MLB history. In the same game Rafael Devers became the youngest player with six hits and four doubles in a single game. And in a season of turmoil and misplaced expectations, Dave Dombrowski had to feel some satisfaction knowing he made the right decision in the winter of 2016.

While criticism will always be quick in New England, the Red Sox GM pulled off a fantastic move and set the Red Sox up in prime position to win a World Series. A feat that was accomplished due to his aggressive nature.