This is the second and final part of my look into Dave Dombrowski's trades with the Red Sox. The last part featured trades 12-7, while this article will look at his six best trades. Most of the trades in this article were crucial to Boston's 2018 World Series Title.
Boston Receives: Drew Pomeranz & San Diego Receives Anderson Espinoza
This trade may seem a little high, as most people view this as Dombrowski's biggest failure, but this trade did not turn out bad for the Red Sox. Dombrowski had a chance to undo these trade once the MLB investigated the Padres and found out they withheld medicals from the Red Sox, but Dombrowski made the right decision by sticking with Pomeranz.
Pomeranz did not have a great 2016 season in Boston following the trade, as he posted a a 4.59 ERA and a 1.353 WHIP in 14 games, but the former Padre bounced back in 2018. Pomeranz had a 3.32 ERA and a 17-6 record cementing himself as the #2 pitcher behind Chris Sale.
Pomeranz fell off a cliff in 2019 with a 6.08 ERA and 1.770 WHIP in 11 starts, but as the Giants showed, the Red Sox were using him incorrectly. If Boston committed to making Pomeranz a back of the bullpen arm, they could have had a left-handed reliever that could hit 98mph on the gun.
Pomeranz could have been the perfect bridge to Kimbrel as evident by his 2.39 ERA and and 45Ks in 26.1 IP with Milwaukee after being dealt to them at the deadline.
The main reason as to why this trade is not a failure is because Anderson Espinoza did not pan out. At the time of the trade, Espinoza was the 13th best prospect in baseball and drew comparisons to Pedro Martinez. This projection did not come to fruition as the 21-year old has not thrown a pitch since 2016 and has had two Tommy John surgeries since joining San Diego's farm system.
Espinoza will most likely not be healthy again until August of this season, so Boston did not miss out on this prospect. Dombrowski made the right decision by sticking with Pomeranz because he would have been stuck with an injury prone pitcher that could not pass a physical.
Pomeranz actually had a 3.9 WAR in his three years in Boston, so he contributed positively to the Red Sox organization. Dombrowski got a stellar 2018 season out of Pomeranz, and it only took a high ranked prospect who has not stayed healthy since 2016.
5. Boston Receives: Brad Ziegler & Arizona Receives: Jose Almonte and Luis Alejandro Basabe
This very well could have been Dombrowski's best trade as a member of the Red Sox if Ziegler had played a pivotal role in a World Series Title. Ziegler became a lights out reliever with the Sox, as he posted a 1.52 ERA, as well as totaling four saves in 33 games as the bridge to the Craig Kimbrel.
The biggest plus of this trade is that Dombrowski did not even give up a top 30 prospect in the farm system for Ziegler, which was considered a drastic underpay at the time.
The highlight of Ziegler's time in Boston came against his former team, when he inherited a bases loaded jam with no outs and a three run lead in the 8th inning of a crucial August game.
He got out of the jam with three strikeouts on 10 pitches to blank the Diamondbacks and uphold the three run lead. Ziegler had a magical half season with the Red Sox that usually goes overlooked when discussing Dombrowski's time in Boston.
4. Boston Receives: Craig Kimbrel & San Diego Receives: Manuel Margot, Javy Guerra, Carlos Asuaje, and Logan Allen
Dombrowski's first move as the President of Baseball Operations was to trade the the 25th (Margot) and 76th (Guerra) ranked prospects in baseball, as well as two other unranked prospects, to acquire quite possibly the best closer in baseball.
As a regular season closer Kimbrel was almost unhittable in his three years as a Red Sox. He had a 90% save percentage, with 108 saves in 119 opportunities, as well as a 2.44 ERA, 0.906 WHIP, and 305Ks in 184.1 IP.
Kimbrel would run into trouble in the postseason, as evident by his 5.14 ERA in the playoffs. But even with those struggles Kimbrel played a big role in getting Boston to the playoffs in three consecutive seasons. And he was essentially the Konami Code when it came to the regular season, which is why this trade is so high on the list.
Another reason for this ranking is that the prospects that Dombrowski gave up did not pan out. Carlos Asuaje is now playing in the KBO, Logan Allen was traded to the Cleveland Indians, Javy Guerra transitioned from an infielder to a reliever with very little success, and Manuel Margot was just traded to the Tampa Bay Rays.
Overall, this was a very good trade for Dombrowski, and while Kimbrel did not have postseason success, he still contributed 42 saves in Boston's 108 win season.
Boston Receives: Chris Sale & White Sox Receive: Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz
This may be surprising to have Chris Sale as Dombrowski’s third best trade, but the next two were buy low options that paid off massively. You knew you were getting one of the best starting pitchers in baseball with Chris Sale, which is why the Red Sox had to give up top prospects to get the deal done.
This is Dombrowski’s most expensive trade, as he gave up two top 100 prospects in Moncada (1st) and Kopech (30th) to acquire Sale, but it worked out. Moncada will be a force at the top of the White Sox’s lineup for years to come, while Kopech could make a difference in Chicago’s starting rotation this season.
Boston did give up a lot, but they received a perennial Cy Young candidate who has posted a 3.08 ERA and a 0.907 WHIP, along with 763Ks in 519.2 IP, in his three years in Boston. But Chris Sale’s biggest achievement is striking out Manny Machado to claim the 2018 World Series Title.
It is highly likely that Boston would not have won a World Series without the trade for Chris Sale. It did cost a pretty penny to acquire the former Chicago White Sox ace, but it was all worth it at the end of the day.
2. Boston Receives: Nathan Eovaldi & Tampa Bay Receives: Jalen Beeks
Dombrowski received a lot of flak for this trade when it happened, considering he gave up the club’s 15th best prospect in Jalen Beeks for a starting pitcher that had just returned from his second Tommy John surgery.
This proved to be an excellent move, as Beeks had a 12.79 ERA in three appearances with Boston in 2018. Clearly Beeks was not ready to contribute to a World Series run, but Dombrowski landed a power-right hander that could contribute. Eovaldi posted a 3.33 ERA in 2018 for Boston, but he saved his best work for the postseason.
In the 2018 playoffs, Eovaldi made 6
six appearances totaling 22.1 innings with a 1.61 ERA and a 0.806 WHIP. More importantly, the former Tampa Bay Ray had a masterful six inning performance in Game 3 of the World Series that saved the bullpen in an 18-inning affair.
The Red Sox most likely would not have won the World Series in 2018 if not for the acquisition of Eovaldi. He made multiple appearances out of the bullpen on short rest in the postseason, and he did a phenomenal job at shutting the door against the Yankees, Astros, and Dodgers.
#1 Boston Receives: Steve Pearce & Toronto Receives: Santiago Espinal
Of all the trades Dombrowski made, the Steve Pearce trade I s by far his most under the radar acquisition. It will not typically be thought of as his best trade, but Dombrowski acquired the 2018 World Series MVP for a non-top 30 Red Sox prospect.
Pearce had a slash line of .279/.394/.507 in 50 games with Boston in 2018, to go along with seven HRs and 26 RBIs. He followed up his regular season with a stellar World Series performance that included a 1.667 OPS and three HRs, which was enough to claim the WS MVP.
Steve Pearce played a pivotal role in Boston’s 2018 World Series Title run, and all it took was a middle-infield prospect that was nowhere near a top commodity in the Red Sox farm system.
Featured image via Kevork Djansezian/Getty Images