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Reflecting on the Red Sox Front Office

Updated: Nov 4, 2022


The 2021 Boston Red Sox who headed for Spring Training with +5000 odds to win the World Series defied expectations. More than a year earlier and before Spring Training in 2020, newly hired Chief Baseball Officer Chaim Bloom traded superstar outfielder Mookie Betts to the Los Angeles Dodgers, officially confirming the Red Sox would not provide Betts the substantial long term contract he was ultimately looking for when he reached free agency after the 2020 season. Betts – the 2018 American League MVP and four-time Gold Glove winner in six seasons with the Red Sox – had a phenomenal career in Boston, but his tenure with the Red Sox was not for long. Both he and the team moved on. Just as he helped lead the Red Sox to a World Series victory in 2018, Betts did the same for the Dodgers in his first season in Los Angeles and received the second World Series ring of his career. He also inked the contract he was looking for when he signed a 12-year, $365 million deal. Betts now won’t be a free agent until 2033, so long as he makes it through the length of his contract with the Dodgers. But back to the Red Sox. Trading Mookie Betts objectively made the Red Sox Major League roster worse entering 2020, and the return, headlined by Alex Verdugo and Jeter Downs, was not viewed as a slam dunk by any means. Some Red Sox fans loathed the trade even more for the sole reason one of the players their team received was in fact named after familiar foe Derek Jeter. The Red Sox finished the 2020 pandemic shortened season at the bottom of the AL East. Only three other teams had a winning percentage lower than Boston’s .400. No matter how you sliced it, though, the 2020 season was never going to be smooth for the Red Sox. It was a bridge season to 2021 and beyond. But because of clutch performances from several players, the return of manager Alex Cora and a determined front office which keenly assembled a roster that blew outside expectations out of the water, the 2021 season proved to be much better than the 2020 season. Perhaps the reality is no trade return would have been viewed as enough for Mookie Betts and trading a homegrown stud across the country in exchange for the best value the team could before it was too late was the most logical choice. The decision to trade Betts given his inevitable departure from Boston aligned with Bloom’s desire to put forth a sustainable product on the diamond that could consistently compete for championships year in and year out. Like many decisions Bloom has made since he initially took over as the leader of the club’s baseball operations, Bloom made the Betts trade with one eye on the present just as much as did with one eye on the future. The Red Sox front office moved past the trade knowing it still had many of the leaders of the 2018 championship team in place to build around, wanted to explore the most optimal use of its resources, and had its sights set on adding depth and under the radar players to its roster. The Bloom-led Red Sox front office has been absolutely intentional with every transaction and baseball decision it made. Boston’s ALCS-clinching win over the Tampa Bay Rays Bloom’s former organization – featured significant contributions from several players, many whose arrivals to Boston did not garner much attention at the time they occurred. Rule 5 draft pick Garrett Whitlock, acquired from the Yankees just one year earlier, held a formidable Rays lineup hitless in the eighth and ninth innings before Danny Santana, a minor league free agent signee less than 12 months before, crossed home plate as the winning run following a sacrifice fly off the bat of Kike Hernandez. Before the season, the Red Sox signed Hunter Renfroe to a modest 1-year, $3 million deal he then proceeded to mash 31 home runs and record 96 runs batted in across 144 games. The Red Sox received a notable contribution from essentially each player up and down the roster while defeating an incredibly talented Rays team that won 100 games in the regular season and entered the postseason as the top seed in the American League. The Red Sox front office consists of many baseball operations personnel whose diligent efforts exemplify a keen commitment and thoughtful approach to continued success. Since 2004, the club has hoisted the Commissioner's Trophy four times, and as of this writing, the ending of the Red Sox 2021 postseason story remains unwritten. Because of the efforts the Red Sox have made toward building an organization suited for sustained success, the Red Sox figure to have at least a decent shot to reach the ALCS or Fall Classic every year for the foreseeable future.

For this, Red Sox fans are fortunate. It’s no secret Fenway Park is a special setting for October baseball, and as long as the front office, players and coaches all combine to ensure the Red Sox get there, the team’s loyal fan base will keep showing up at the beloved ballpark, eager to see which player becomes the next to announce himself as the latest Red Sox postseason legend or cement himself into the team’s decorated history. That player may earn more than $30 million a year, have ascended quickly through the Red Sox organization, or hit in the third spot of the lineup. Or they can be someone who was never previously afforded a legitimate everyday opportunity in their career but seized the moment once the Red Sox gave them their chance. Who the future Red Sox heroes will be depends on who Bloom and his fellow determined front office colleagues bring to the team and what transpires from there.

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