The first of February marked the end of an era for the Boston Red Sox with franchise icon Dustin Pedroia announcing his retirement. Pedroia oversaw one of the most prolific stretches of success for the Red Sox franchise, bringing home three World Series titles over the course of his fourteen-year career. That said, it’s been a trying few seasons for the Fenway Faithful. Whether it be drama at the manager position, front office instability, or a middling roster rich with star power, but low on depth, the Red Sox find themselves in an unenviable position. Should they tear it all down and start from scratch? Or should they push all their chips forward and go all in for one last chance at postseason glory? However, judging from the team’s transactional report, it’s clear that they themselves aren’t really sure what they want to do.

All In: The Red Sox as Contenders

Looking at the current state of the AL East, it’s not inconceivable that the Red Sox could challenge for a divisional crown in 2021. The Tampa Bay Rays have seen their starting rotation gutted, either through departures via free agency (farewell, Charlie Morton) or the self-inflicted wound of trading away staff ace Blake Snell. The New York Yankees have arguably baseball’s most intimidating lineup, but their rotation could implode just as easily as it could dominate. The Toronto Blue Jays have a young and exciting core, but still lack quality starting pitching depth. The Baltimore Orioles…yeah, we all know they aren’t going to be a factor in 2021. Does Boston have holes in their starting rotation? Sure, but a return to form by Eduardo Rodriguez would go a long way in solidifying the top end of the Sox rotation.

Up until Wednesday, it seemed fairly clear that the Red Sox were building their team to contend in 2021. Xander Bogaerts and Rafael Devers represent one of the league’s best left sides of the infield and J.D. Martinez will almost certainly bounce back in 2021. Him getting hit in the hand by a 95 MPH fastball by Nat’s reliever Daniel Hudson on August 30th hampered his performance a lot more than we realize. Despite not going on the disabled list, looking at his underlying numbers, there was a clear decline in his exit velocity, hard-hit rate, and barrels. His approach at the plate and his ability to swing with confidence makes sense if he was fighting his way through injury. A clean bill of health should allow him to return near the form we saw in years past.

Aside from franchise stalwarts Bogaerts, Devers, and Martinez, the Sox saw a career year from backstop Christian Vazquez in 2020 as well as the development of the aforementioned Alex Verdugo. The additions of super utilityman, Kiké Hernández, and Mike Trout doppelganger, Hunter Renfroe, should also provide the Sox with some additional pop in their lineup. On the mound, the Red Sox have made a series of savvy investments the past few weeks, trading for strikeout machine, Adam Ottavino, signing swingman Matt Andriese and oft-injured starter Garrett Richards, while also re-upping Martin Perez to fill out the backend of the rotation. All of these moves are indicative of a team adding pieces to complement their core.

In some ways, the Red Sox are similar to the Philadelphia Phillies. An explosive offense complimented by a suspect starting rotation and questions in the bullpen. While the Red Sox have more questions at the top end of their rotation (namely the health of Chris Sale and E-Rod), there’s a lot to like here if you’re an optimist. One can only wonder what Kiké Hernández can do if given an everyday spot in the lineup at one position.

All of which make what transpired on this past Wednesday that much more confusing.

Bye-Bye, Benintendi

Andrew Benintendi’s legacy in Boston will be one of unfulfilled potential and a career arc stunted by injury. (Credit: Kim Klement/USA TODAY Sports Images)

Perhaps this move makes sense if you’re consumed by recency bias. Yes, Andrew Benintendi was horrible in 2020. He struck out in nearly 50% of his plate appearances in a campaign lost to injury. Still, I have trouble believing that a package headlined by Franchy Cordero or Josh Winckowski will amount to anything more than organizational fillers at this point in their careers. Is that what Benintendi is worth? A couple of guys to fill out spots in AA and AAA? Cordero has legitimate power, but he strikes out far too often (34.9% career rate) to be a lineup regular. Winckowski was never seen as more than a potential middle-relief arm until a recent uptick in fastball velocity.

Compare that to Benintendi: from 2017-2019, Benintendi accounted for 49 home runs, 245 RBI, 107 doubles, and 51 stolen bases. He’s a five-tool player in the outfield. It’s bizarre that the Red Sox would settle for two relatively low-level prospects prior to the 2021 season rather than ride out the first half of the year and see if Benintendi can build up his trade value at all. Let’s be honest, Benintendi’s value can’t get any lower at this point; were he to play as he had in 2017 and 2018, you have to imagine he’d bring in a lot more than what the Red Sox got on Wednesday if they chose to trade him at the deadline in July.

I have trouble buying Chaim’s claim here. Sure, you got some quantity in this trade, but quality? I’m not so sure. The departure of Benintendi further deconstructs a Red Sox team that was World Series champions just a few seasons ago. The loss of Mookie Betts and David Price was a crippling blow to this franchise. Replacing them was a longshot. Still, they were plenty good enough to compete in 2021. Why throw in the towel on one of your team’s best players before the season even began?

This all feels particularly odd considering that the Red Sox payroll is the lowest it’s been in years. Why weren’t they bigger players in pursuing some of the off-season’s more prized free agents? Where were they in the George Springer sweepstakes? Imagine him roaming centerfield at Fenway, playing ping-pong with the Green Monster when he is at the plate. Where were they in the Trevor Bauer sweepstakes? He’d play a fine second fiddle to either Chris Sale or Eduardo Rodriguez if they’re able to return from injury. The Red Sox were largely absent from these conversations despite their reputation as big spenders in the past. Is this a new mindset by chief baseball officer Chaim Bloom? What’s their endgame here?

Where Do the Red Sox Go From Here?

Trading away one of your best players (Andrew Benintendi), despite his recent struggles, whilst taking out flier deals on guys like Garrett Richards, Matt Andriese, and Martin Perez represent two different mindsets. Are the Boston Red Sox working on building a deep championship contender? Or are they looking to become sellers? At this point, I honestly can’t tell. If you’re a Sox fan, I can’t imagine you’re feeling good when the ship you’re on doesn’t seem to have a clear course with a future very much in doubt.

Three Up, Three Down is a weekly roundup of three news stories from around Major League Baseball. The focus of each edition will rotate on a divisional basis. This week’s top news stories out of the AL East are the bizarre offseason plan of the Boston Red Sox, the rise of Ray’s prospect Wander Franco, and the construction of a high-risk, high-reward rotation in the Big Apple.