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The Boston Red Sox Traded Away Their Best Player — Again

Rafael Devers joins Mookie Betts and Xander Bogaerts as superstars the Boston Red Sox decided not to retain as their losing run continues.

The Boston Red Sox have the most World Series titles (four) since 2000, most recently in 2018. In the Game 5 win over the Los Angeles Dodgers that October, 25-year-old superstar outfielder Mookie Betts led off, 25-year-old star shortstop Xander Bogaerts hit fifth, and a 21-year-old budding star named Rafael Devers was in the seventh spot. They were deemed the future of the team, the pillars of a franchise set up incredibly well for sustained, long-term success.

Instead, the Red Sox have not played in a World Series game since. They haven’t made the playoffs since 2021 and could easily miss the postseason for the fourth straight season, which Boston hasn’t done since the early 1990s. And after the Red Sox dumped Devers in a massive blockbuster trade to the San Francisco Giants on Sunday night, the entire trio of what should have been franchise cornerstones now all reside elsewhere. In the last seven years since that championship, ownership and management have made bafflingly bad decisions at nearly every turn.

Devers, who was dealt for a pair of struggling starting pitchers and two minor leaguers, is in the third year of a 10-year, $313.5 million contract that was brokered in many ways to rectify the mistake of not locking up Betts. After winning American League MVP in 2018 and putting up another All-Star season in 2019, Boston ownership led by John Henry was reluctant to sign Betts — the epitome of a franchise player both on and off the field — to a team-record extension he was asking for a year before he was set to hit free agency. So the Red Sox, now led by new president of baseball operations Chaim Bloom, months after they fired longtime championship-winning exec Dave Dombrowski, traded him to the Dodgers in the 2020 offseason for a group of players and prospects that came nowhere near approaching Betts’ immense value.

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A year later, LA gave Betts the 12-year, $365 million extension he should have received from the Red Sox, who more than anyone should have recognized that he was the exact type of hitter, defender, clubhouse leader, and teammate you want to build around. Since then, Betts has moved from the outfield to second base to shortstop, selflessly adapting to the team’s needs and leading the Dodgers to two World Series titles. After being named an All-Star in 2019, 2021, and 2022 (COVID canceled the 2020 edition), the Red Sox let Bogaerts leave in free agency after the 2022 season, inking an 11-year, $280 million deal with the San Diego Padres.

Trading Betts and deciding not to retain Bogaerts were deeply unpopular moves among the team’s fan base and antithetical to how a storied franchise like Boston should be operating, though the Bogaerts deal hasn’t aged too well. Boston should be building around young star players and supplementing them with marquee trades and free agency signings. It was that line of thinking, along with a peace offering to irate fans, that led Henry and Bloom to give Devers his extension before the 2023 season.

Boston finally doled out the $300 million contract Betts should’ve been offered, giving Red Sox fans a player they can rally behind, buy their jersey, and root for. But since that 2022 season, Henry’s Red Sox have not had one of the 10 largest payrolls in Major League Baseball, per Spotrac, depriving fans of the proper support they deserve. After Bloom was fired in September 2023, new lead executive Craig Breslow made a splash this past offseason by signing All-Star Alex Bregman to a three-year, $120 million deal.

The only problem was that Bregman plays third base, the same position as Devers. That proved to be the beginning of the end of Devers’ nine-season tenure in Boston. There were reports that, unlike how Betts adapted to new positions in Los Angeles, Devers wasn’t pleased that he was being asked to accommodate Bregman’s superior defense.

Other reports suggested that Devers was frustrated by mixed messaging within the organization and was being used as a scapegoat for a relationship that had become irreparable. But Devers, a three-time All-Star beloved by teammates and fans alike, is someone you bend over backwards to accommodate and support as a franchise.

Since the start of the 2021 season, per StatMuse, Devers is eighth in MLB in OPS, ninth in total hits, eighth in home runs, seventh in RBIs, and 12th in runs scored. Like Betts and Bogaerts, that’s the type of player you build around and try to patch things up with, not someone to dump when things get tough. If you’re a superstar player looking for a lucrative, successful, stable franchise, Henry and the Red Sox have proven over the last five years that they cannot and should not be trusted.

Boston now seems content to build around a new set of top young prospects coming up, led by Roman Anthony, Kristian Campbell, and Marcelo Mayer. Hopefully, for their sake and the faithful, loyal, and avid Red Sox fans, Henry and management will learn to respect and take care of their stars, rather than kicking them to the curb when times get tough or inconvenient.

The franchise’s future depends on it.

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Shlomo Sprung

Shlomo Sprung is a Senior Staff Writer at Boardroom. He has more than a decade of experience in journalism, with past work appearing in Forbes, MLB.com, Awful Announcing, and The Sporting News. He graduated from the Columbia University Graduate School of Journalism in 2011, and his Twitter and Spotify addictions are well under control. Just ask him.