Boston Red Sox biggest trades under Dave Dombrowski
Dave Dombrowski is known as one of the most aggressive executives in baseball. Let’s look at some of his biggest trades during his tenure with the Red Sox.
Dealin’ Dave was brought to Boston to win. At the time of his hiring in 2015, the Red Sox had a top-five farm system in baseball and were just finishing up their second consecutive season at the bottom of the AL East. He was just as advertised: fearless in his trades and careless in his management of the farm system. He departed in 2019 with a World Series ring on his finger and the worst farm system in the MLB.
Dave Dombrowski was the physical embodiment of the “swing big or miss big” philosophy. As a result, the rewards were sweet―three consecutive AL East titles and a 119-win championship season―but the consequences were painful, with the Red Sox coming off a disappointing third-place season and possibly facing another.
So without further ado, let’s look back at Dombrowski’s biggest trades from his tenure with the Red Sox.
Manuel Margot, Javier Guerra, Carlos Asuaje, and Logan Allen for Craig Kimbrel
Dombrowski hit the ground running with the acquisition of star closer Craig Kimbrel. Dealin’ Dave did what Dealin’ Dave does best, acquiring the best available player for a valuable package of prospects.
By 2015, Kimbrel had already been an All-Star four times, won NL Reliever of the Year, and had received MVP votes in three seasons. The Red Sox sent the Padres prized outfielder Manuel Margot, along with Javier Guerra, Carlos Asuaje, and Logan Allen.
Margot has played three full seasons in the majors and has a career OPS under .700. Guerra has given up on becoming an infielder and converted to a relief pitcher. Asuaje is a 28-year-old who spent all of 2019 in the minor leagues. Allen has turned out to be the most valuable piece. He is 22 years old and was ranked as the Indians No. 5 prospect last year, after being dealt in the Trevor Bauer/Yasiel Puig trade.
On the other hand, Kimbrel was an All-Star in all three years with Boston. Though his first All-Star nomination in 2016 may have been more due to his previous performance than his abilities at the time, he bounced back in a major way in 2017. He won AL Reliever of the Year with a 1.43 ERA and was a finalist again in 2018.
Though his performance during the Red Sox World Championship run was far from his typical standard, he was able to come through when he was needed most, converting all six of his save opportunities and closing out both the ALDS and ALCS.
Kimbrel was allowed to walk after the 2018 season, eventually signing with the Chicago Cubs. His absence was sorely felt in the bullpen. The Red Sox blew 48% of their save opportunities last season, leading to a disappointing third-place AL East finish.
Looking back, it seems that the Kimbrel deal was quite successful for the Red Sox, who were able to acquire an elite closer without losing any very valuable pieces.
Travis Shaw, Josh Pennington, Mauricio Dubon, and Yeison Coca for Tyler Thornburg
This trade made perfect sense at the time. Travis Shaw fell short of expectations during the 2016 season and got relegated to a platoon role with Aaron Hill in July. As he continued to struggle down the stretch, he was replaced by Brock Holt and did not start a single postseason game. He would finish the season with a .242 average and 16 home runs.
Pablo Sandoval had disappointed in 2015 and was injured for almost all of 2016. The main complaint was about his work ethic, with reports of him being on Instagram during a game and lack of discipline with his weight. The memory of his belt breaking after a swing remained firmly in everyone’s minds. However, reports of his weight loss and revitalized desire to become the excellent player he once was began to convince people that he was due for a comeback season.
Hanley Ramirez had cemented his role at first base (Shaw’s other position) after hitting 30 home runs with a .286 batting average. There was simply nowhere for Shaw to play.
On the other hand, Tyler Thornburg was coming off a breakout season in which he posted a 2.15 ERA and 2.83 FIP in 67 innings out of the bullpen for the Milwaukee Brewers. He was entering his first year of arbitration and would be under control for three years.
With Koji Uehara and Junichi Tazawa both hitting free agency, the Red Sox needed an elite relief arm to serve as the setup man for Kimbrel.
In December of 2016, the Red Sox sent Shaw, Josh Pennington, Mauricio Dubon, and Yeison Coca (later added to the trade) to the Brewers for Thornburg.
Pennington never reached the majors and retired due to arm issues. Dubon broke into the league in 2019 at the age of 24, but was traded to the Giants and is currently their No. 11 prospect. Yeison Coca was barely above the Mendoza Line in Single-A last year.
On the other hand, Shaw posted two 30-HR seasons with the Brewers in 2017 and 2018, while the Red Sox flailed about trying to find a steady starter at third base. 10 different players tried the position for Boston in 2017, with none of them finding steady success until the call up of Rafael Devers.
Thornburg missed all of 2017 with an arm injury. Health problems and under-performance continued to plague him, and he finished his time in Boston having pitched only 42.4 innings with a 6.54 ERA.
In the end, we can safely say that this was one of the worst trades in recent memory, with the Red Sox giving up a talented contributor while receiving very little production in return.
Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz for Chris Sale
Chris Sale being traded to the Red Sox was the talk of the offseason in 2017. It was a highly controversial deal, which saw Yoan Moncada (No. 5 overall prospect at the time) and Michael Kopech (No. 36 overall prospect) along with Luis Alexander Basabe and Victor Diaz being sent to the White Sox.
At the time of the trade, Sale had finished in the top six in Cy Young voting for five consecutive seasons and was owed just $39.5 million over the next three years. Since becoming a starter, he averaged 29.6 starts per season, never having missed an extended period of time due to an injury. He was easily the best available pitcher that offseason and Dealin’ Dave pulled the trigger.
Sale has been just as advertised for the Red Sox, finishing second and fourth in the Cy Young voting during his first two seasons. For some time, the lanky lefty’s ability to pitch in the playoffs was in doubt, as his career postseason ERA was 5.76. Recent findings regarding the Astros’ sign-stealing scandal perhaps provide an explanation though. Excluding his 2017 start in Houston, Sale’s postseason ERA is 4.05 and his FIP is 2.71.
His 4.40 ERA from last year may also look ugly, but a deeper dive into the stats provides more insight. To begin, his FIP was 3.39, indicating that his high ERA may be the result of bad batted ball luck.
Furthermore, former manager Alex Cora only allowed Sale to have two Spring Training starts in an attempt to reduce his workload. This strategy backfired in a big way, as Sale posted an 8.50 ERA and 6.10 FIP over his first four games. These struggles were not unique to him either. Rick Porcello’s appearances were similarly limited during spring training and struggled to the tune of an 8.47 ERA and 6.80 FIP over his first four starts. For the next 17 games,
Sale was the ace Boston knew and loved. He pitched to a 3.24 ERA and 2.40 FIP from April 23 through July 23 and had the Red Sox just 2.5 games out of the second Wild Card spot. However, an attempt to pitch through an injury late in the season saw his ERA balloon once again, and he posted a 6.46 ERA and 4.10 FIP in his final four starts before he was shut down for good.
Put simply, Sale was more or less the same elite pitcher in 2019―he was just put in a very difficult position to succeed.
Over in Chicago, Moncada is blossoming into the star the Red Sox hoped he’d become when they signed him out of Cuba. He hit .315 with 25 home runs last season. Though his high batting average can be partially explained by a .406 BABIP, that is not entirely due to good batted ball luck. He had an average exit velocity of 92.8 mph, which was in the top 3% in the majors, per Baseball Savant. Although his fielding is subpar (-4 DRS) and he does not take many walks, he is still 24 years old and will likely continue to improve.
Despite Tommy John surgery causing him to miss all of 2019, Kopech enters 2020 as the 20th best prospect in all of baseball. Luis Alexander Basabe is the No. 7 prospect in a stacked White Sox farm system. Victor Diaz was not one of the team’s top 50 prospects.
Even though the Red Sox gave up a valuable package of young players, they were able to receive a Hall of Fame caliber ace for three years under a team-friendly contract. While Red Sox fans will undoubtedly watch the careers of Moncada and Kopech closely, for now, it seems as though this deal was a win for both sides (this does not include Sale’s seemingly disastrous extension).
Anderson Espinoza for Drew Pomeranz
This deal was a head-scratcher at the time. Anderson Espinoza was one of the top 40 prospects in baseball, and while Drew Pomeranz was in the middle of an All-Star season, he had spent most of his career as either a mediocre starter or above average reliever. Also, the 102 innings he had pitched for the Padres that season was already a career high.
Pomeranz may not have performed up to the standard of a player who gets traded for a blue-chip prospect, but the trade turned out even worse for the Padres, as Espinoza has missed three consecutive seasons due to two Tommy John surgeries.
Pomeranz’s first stint with the Red Sox in 2016 was unspectacular, posting a 4.59 ERA and giving up a game-deciding home run to eliminate the Red Sox in Game 3 of the ALDS. However, when Price went on the IL and Porcello struggled in 2017, Pomeranz stepped up as the No. 2 starter. He went 17-6 with a 3.32 ERA, leading Boston to a second consecutive division title. Although he got rocked at Minute Maid Park by the Astros in the playoffs, one can argue that it was not entirely his fault.
Unfortunately, he followed that up in 2018 with the worst season of his career. After pitching to a 6.31 ERA in his first 11 starts, he was demoted to the bullpen. If the Red Sox thought keeping him out of high-pressure situations would help, they were wrong. He continued to struggle, with a 5.56 ERA as a reliever.
After being left off the roster during the ALDS and ALCS, an injury to Steven Wright allowed “Big Smooth” to make the World Series roster. Even so, former manager Alex Cora made his level of trust in Pomeranz very clear in World Series Game 3, where Pomeranz was the only man remaining in the bullpen and Cora allowed Nathan Eovaldi to throw 97 pitches in relief―a World Series record―on just one day of rest.
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When Dombrowski was hired by the Red Sox, they had the best farm system in baseball. At the time of his departure, they had the worst. With those resources, he brought the Red Sox three division titles and a World Series trophy. However, his ability to recognize prospects that should be deemed untouchable should not be overlooked. By moving Espinoza instead of Devers, Moncada instead of Benintendi, and Kopech instead of Chavis, he has set the team up with a very solid young core for the foreseeable future.