Dave Dombrowski’s four-year tenure in Boston brought a World Series Championship and three AL East Division Titles to the Red Sox organization. Dombrowski earned himself the nickname “Dealin’ Dave” for his vast amount of trades over the course of his 41-year career in baseball. As the President of Baseball Operations with the Red Sox, Dombrowski completed 20 trades with varying degrees of success.
After browsing through all 20 trades, I labeled six as washes considering neither side came out on top, and there are also two that have yet to play out. I ranked the other 12 trades from best to worst based on who they got back and what they gave up. You will most likely be surprised as to how well Dombrowski did.
12. Boston Receives: Tyler Thornburg & Milwaukee Receives: Travis Shaw, Josh Pennington, Mauricio Dubon and PTBNL (Yeison Coca)
The Tyler Thornburg trade is Dombrowski's most notable failure, as Thornburg never lived up to the hype built up around him. The former Brewer missed the entire 2017 season due to a shoulder injury suffered in Spring Training.
After returning from injury, Thornburg never found that magic he had in Milwaukee as he posted a 6.54 ERA in 41 appearances across 2018 and 2019. Eventually, Boston cut bait with the reliever as he never became that back of the bullpen arm that he was brought in to be.
The biggest piece the Red Sox lost in this trade was Travis Shaw. By trading Shaw before the 2017 season, Boston put all their faith in Pablo Sandoval to be the permanent third baseman. That failed as spectacularly as the movie Cats at the box office.
Shaw went on to hit 63 home runs with 187 RBIs across 2017 and 2018, but he slowed down in 2019 hitting .157/.281/.270, which led to multiple minor league stints, and eventually being non-tendered this past off-season.
Boston gave up their 12th ranked and 22nd ranked prospects in Mauricio Dubon and Josh Pennington in this trade. The Brewers shipped Dubon to the Giants at last season's trade deadline, while Pennington retired from baseball in 2018.
None of the pieces Boston gave up ended up being permanent fixtures in Milwaukee, but Tyler Thornburg was a complete disaster, which is why this is Dombrowski's worst trade.
The only saving grace of this trade is that Boston had to call up Rafael Devers earlier than expected due to the gaping hole at third base. Devers made his debut towards the end of July of 2017, and notably hit a game tying ninth inning opposite field home run off of Aroldis Chapman at Yankee Stadium.
11. Boston Receives: Andrew Cashner & Baltimore Receives: Elio Prado and Noelberth Romero
Andrew Cashner was the lone addition at the 2019 trade deadline for Boston, and it did not pan out. Cashner contributed negatively to the Red Sox as evident by his -0.2 WAR. Dombrowski would have been better off standing pat at the deadline as this trade did not push the team to playoff contention.
This could end up being Dombrowski's worst trade, as Elio Prado and Noelberth are both 17 year old Dominican Summer League prospects who could very well turn out to be superstars, but they do have the chance to fizzle out before progressing far in Baltimore's farm system.
10. Boston Receives: Eduardo Nunez & San Francisco Receives: Gregory Santos and Shaun Anderson
It may seem a little surprising to see Eduardo Nunez this low on this list, but I am only considering trades Dombrowski made and not free agent signings. Nunez had an expiring deal when the Red Sox acquired him at the 2017 Trade Deadline. He then re-signed with Boston the following off-season, so 2018-2019 would count toward free agent signing years, while only 2017 encompasses his trade value.
Nunez caught lightning in a bottle as a member of the 2017 Red Sox with a batting average of .321 and a slugging percentage of .539 in 38 games. His season would sadly end in injury; however, as he collapsed while running to first in game 1 of the ALDS.
Nunez would go on to play a key part in Boston's 2018 Title run, but injuries plagued his 2018 season. Just like the Andrew Cashner trade, Dombrowski gave up a 17-year old Rookie ball prospect in Gregory Santos, who has shown promise in his short A-ball stint with the Giants. This is another trade that could pan out to be much worse depending on how Santos develops.
9. Boston Receives: Ian Kinsler & Angels Receive: Ty Buttrey and William Jerez
Dombrowski traded Boston's 19th and 23rd ranked prospects in Ty Buttrey and William Jerez in exchange for veteran Ian Kinsler. Dustin Pedroia's injury left Boston without a set second baseman during their Title run. Dombrowski brought in Kinsler to be the starting second baseman for the remainder of the season.
Kinsler did not provide much offense or any spectacular fielding, but he was a better option than Eduardo Nunez or Brock Holt. This trade is towards the bottom of the list more for what Boston gave up rather than what they received.
William Jerez did not do anything with the Angels, but Ty Buttrey turned out to be a solid reliever. In his two seasons with LAA, he has a 3.86 ERA with 104 Ks in 88.2 IP. Buttrey could have been a solid contributor to Boston's pen, especially considering that Ian Kinsler was not a necessity to Boston's 2018 World Series Title.
8. Boston Receives: Addison Reed & Mets Receive: Stephen Nogosek, Jamie Callahan, and Gerson Bautista
Boston gave up their 18th, 23rd, and 28th ranked prospects to acquire Addison Reed at the 2017 Trade Deadline. Reed had a decent half season as a Red Sox with a 3.33 ERA in 29 appearances, but his big issue was his tendency to give up home runs. In Boston he surrendered five HRs in 27 IP, as opposed to the six HRs he gave up as a Met in 49 IP during the first half of the season.
Reed was a positive addition, but he did not boost the Red Sox to a Championship contending team. The good news for the Sox is that Stephen Nogosek is the only prospect who is still with the Mets, and he posted a 10.80 ERA in 7 games with the Mets last season.
Reed did not make a significant difference in Boston's playoff hopes, but the prospects they gave up did not go on to do anything special.
7. Red Sox Receive PTBNL (Josh Taylor) & Arizona Receives: Deven Marrero
This trade may seem a bit high, as most people probably do not even realize this transaction occurred, but this is easily one of Dombrowski's best moves. He turned Deven Marrero, a guy who was out of options and struggled at the plate, into Josh Taylor, who posted a 3.04 ERA with 62 Ks in 47.1 IP out of the bullpen for Boston in 2019.
The most interesting fact about this trade is that the initial compensation for Marrero was a player to be named later. A PTBNL is usually an after thought who does not stay on the roster for very long, but Dombrowski struck gold with Josh Taylor.
Marrero had a .167/.224/.205 slash line in 78 ABs before being released by Arizona, while Taylor will be a key piece to the 2020 Boston bullpen. Taylor proved to be a diamond in the rough that could pay dividends for years to come.
Featured image via Elise Amendola/AP Photo