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.
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.