In the winter of 2016, the Boston Red Sox were in serious discussions with the Chicago White Sox to acquire ace starting pitcher Chris Sale, with Boston viewing the lanky southpaw as the missing link in their quest for a championship. During the negotiations, the White Sox asked the Red Sox to give them a highly coveted prospect for Sale: former number five overall draft pick Andrew Benintendi. The Red Sox said no and offered another trade chip instead: Cuban import Yoan Moncada. The White Sox agreed to the deal, and on Dec. 6, 2016, Sale was sent to Boston for a package of prospects including Moncada, Victor Diaz, Luis Alexander Basabe, and Michael Kopech. Boston managed to acquire one of the best starters in the game in Sale and hold on to a promising young talent in Benintendi.
Sale turned out to be an investment that paid off, confounding major league hitters in 2017-18 and playing a key role in the Red Sox’s historically dominant 2018 championship team. Benintendi was a key contributor on that team as well, hitting .290 with an OPS north of .800, and providing solid defense and baserunning as well. However, the following year, in 2019, things didn't go as well. Sale was severely limited by injuries and did not perform up to standards, while Benintendi slumped. In the 2019-20 offseason, Boston’s ownership made a much-maligned decision to trade beloved homegrown superstar Mookie Betts to the Los Angeles Dodgers. The reasoning behind the trade was that Betts would become a free agent following the 2020 season, and he had essentially told the team that he was determined to hit the open market and had little interest in signing an extension.
The 2020 Major League Baseball season was, like virtually everything on the planet, thrown into turmoil by the COVID-19 pandemic. After much wrangling with the Players’ Association, the MLB owners were finally able to strike a deal on playing a truncated 60-game season. The Red Sox would not do well under these circumstances. They finished 24–36, dead last in the AL East and fourth-worst in the majors. Sale missed the entire year due to Tommy John surgery. Benintendi battled rib injuries and was pitifully bad in the 14 games he played before being shut down, batting just .190 with a .442 OPS.
During the offseason, rumors began to swirl that the Red Sox would move Benintendi, as GM Chaim Bloom had been instructed by ownership to cut payroll after the previous GM, Dave Dombrowski, had taken a free-wheeling approach to spending. With a change in philosophy at the top, Bloom was brought in to do what he had done so well with the small-market Tampa Bay Rays: make good, cost-effective signings, while not letting spending inflate that much. Benintendi’s decline in performance over the last couple years, combined with his impending free agency at the end of the 2022 season, made him a prime trade candidate.
The Sox would do exactly that last week, sending Benintendi to the Kansas City Royals in a three-team deal that also involved the New York Mets. Along with cash considerations, the Red Sox acquired minor league pitcher Josh Winckowski from the Mets and outfielder Franchy Cordero from the Royals, as well as two players to be named later. Certainly, the Red Sox farm system needed replenishing after years of mortgaging the future to compete in the present. But one has to wonder if they could’ve gotten more value for someone like Benintendi, a former top prospect still in his 20s with two more years of team control. Since their 2018 championship, the Sox have been on what feels like a steady dive into irrelevancy. With this trade, it feels like 2021 will be yet another rebuilding year.