It’s a Tough Road Ahead for the Boston Red Sox


The only ‘bright’ side to being an elite team that missed the playoffs is that they get to jump-start their quest for success in the following season.

Unfortunately for the Red Sox, they continue to move forward without a formal general manager at the helm. Until that position has been addressed, even if the hiring is ultimately Eddie Romero, the team cannot expect to construct their roster moving forward.

And with the offseason that they’re in store for? They might need to start as early as possible.

Let’s take a look at each decision the Red Sox front office is going to be tasked with this winter.

The Mookie Betts situation


What made guys like Dave Dombrowski so successful was his ability to lock players down to extensions early. While he continues to get flack for the Chris Sale extension, people tend to forget he got Xander Bogaerts for a bargain of $20 million per season over the next six years (vesting option for year-seven). However, with Dombrowski no longer in the fold, that complicates things a bit.


Since Betts was drafted in 2011, he’s seen Theo Epstein, Ben Cherington, and Dave Dombrowski run out of town. Could the lack of loyalty to World Series-winning executives push the young superstar out of town? If so, do the Red Sox really want an inexperienced general manager executing that potential trade? That remains to be seen.

J.D. Martinez opting out

It’s not a guarantee that the Red Sox slugger opts out of the remaining three years of his contract, but nobody will know until up to five days after the World Series. However, as the Red Sox look to shed salary to reportedly get until the first luxury tax threshold, could they potentially be hoping Martinez walks?


If that’s the plan, what’re the other options to fill that position? Guys like Edwin Encarnacion (club option) and Jose Abreu are free agents to be. Or maybe they’ll opt for the cheaper guy like Justin Smoak or Eric Thames. Regardless, they’ll need to assure that they have a legit power source at designated hitter in 2020 if they want to “shed salary, but remain competitive.”

Brock Holt’s free agency

This ordeal isn’t as dire as Betts and Martinez, but it appears to be in the Red Sox best interest to keep their utility man under wraps for the foreseeable future. The 31-year-old has had a sudden resurgence with the bat, slashing .286/.366/.407 with 106 wRC+ since the start of 2018, but has this vast improvement effectively priced him out of Boston’s future plans?

At the end of the day, a bit of realism has to settle in. While Holt’s value and contributions extend much further than the confines of Fenway Park, he is a guy who is prone to second-half decline in seasons where he plays over 100 games (2018 being the outlier). Are the Red Sox willing to open their pockets and give Holt $10-plus million per season to keep him? That seems to contradict their offseason goal.

Rick Porcello’s free agency

There’s no denying that Rick Porcello wasn’t very good in 2019. His 5.52 ERA, 4.76 FIP, and 5.12 xFIP were all career-worsts for the right-hander. On top of that, his 1.6 HR/9 was the second-worst of his career, and his 2.3 BB/9 was the worst he’s had since his rookie season in 2009.

He’s no longer going to be paid north of $20 million per season, but is his production still not worth a one-year ‘prove it’ contract? It really shouldn’t be, because he’s been amongst the steadiest of starting pitchers since his Red Sox career began in 2015. So in a season following a bottom-half of the league rotation, the team might opt to bring the 30-year-old finesse pitcher back, in hopes that he can figure himself out again.

The bullpen

While the struggles of the Red Sox bullpen in 2019 are a bit overblown, they still need to upgrade certain elements of it.

Brandon Workman had a fantastic season, but it might be in the Red Sox best interest to get a more traditional closer or at least one that doesn’t walk almost six guys per nine innings.

With guys like Dellin Betances, Steve Cishek, and Arodys Vizcaino all available, Boston certainly has the chance to get a proven MLB closer, but will they seize that opportunity? Or will they enter 2020 with another ‘closer by committee” experiment?


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