If Chaim Bloom's Red Sox tenure unfolds as planned, someday we'll marvel at how far the organization came on his watch.
His inaugural roster just delivered a last-place finish and the fourth-worst record in baseball, so when it comes to players who could depart this winter, the short answer is pretty much all of them. Outside of third baseman Rafael Devers, shortstop Xander Bogaerts, and right fielder Alex Verdugo, the Red Sox are depressingly short on building blocks, though they hope that starts to change this offseason.
If we're handicapping the potential candidates to find new homes, it's hard to say whether catcher Christian Vazquez is more likely to be traded than Matt Barnes or Andrew Benintendi or Michael Chavis, though that didn't stop us from undertaking the exercise earlier this month. Expect Bloom to be open for business.
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That said, a handful of players are much less likely to return, and any list has to start with center fielder Jackie Bradley Jr. The club's only free agent of note has ridden the roller coaster over seven seasons in Boston, vacillating between Gold Glove outfielder, postseason hero, and offensive zero. We shouldn't let Bradley's inconsistency cloud that he's going to be a free agent in demand.
He's probably the second-best center fielder on the market, trailing only Astros All-Star George Springer. He's also coming off one of his better offensive seasons after hitting .283 with an .814 OPS. There's rumors that the Astros are already interested in Bradley as a lower-cost replacement for Springer, and any team hoping to add an elite defender without breaking the bank should give him a call.
While there's a chance the Red Sox retain him, his departure feels more likely, if for no other reason than once free agents reach the market, as a general rule they tend to leave. It's also telling that the Red Sox didn't make any extension overtures to Bradley during the season.
He's not the only outfielder who will be in the market for a new home. It's OK if you forgot about him, but Rusney Castillo is finally a free man after serving out the final four years of his seven-year, $72.5 million contract in minor league purgatory. Castillo became a financial liability as part of the 40-man roster, so once the Red Sox removed him, it became clear he would never make it back.
Let the record show that Castillo hit .262 with seven homers in 99 games over parts of three seasons, though his last appearance came in 2016. It's actually conceivable that he finds work next season, because the 33-year-old hit .293 with a .761 OPS over five seasons in the minors. And because he spent so much time there, he's not even arbitration-eligible until 2023. Stranger things have happened.
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Finally, there's Dustin Pedroia. The former All-Star, Rookie of the Year, Gold Glover, and MVP is effectively finished, thanks to a debilitating knee injury. All that's left now is to figure out how to end his career gracefully, since he's still owed the final $12 million on his six-year contract extension.
Pedroia can be removed from the 40-man roster or released, but more the more likely outcome is that the Red Sox reach a settlement similar to the one that allowed David Wright to be paid by the Mets when a back injury ended his career prematurely.
Injuries may have curtailed what looked like a Hall of Fame career, but even without the sendoff he deserved, Pedroia still goes down as an all-time Red Sox great.