Boston Red Sox: Next winter will be a major chapter in the team’s future

BOSTON, MA - DECEMBER 9: Chief Baseball Officer Chaim Bloom of the Boston Red Sox speaks during the 2019 Major League Baseball Winter Meetings on December 9, 2019 in San Diego, California. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA - DECEMBER 9: Chief Baseball Officer Chaim Bloom of the Boston Red Sox speaks during the 2019 Major League Baseball Winter Meetings on December 9, 2019 in San Diego, California. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

The Boston Red Sox made numerous head-scratching moves this winter but next offseason is already shaping up to be more exhausting than 2020.

We’re a few games into spring training and the Red Sox are working with mixed results so far. A quick pair of wins to start the weekend was capped off with a drubbing by the Orioles this afternoon. While all the attention has been placed on this offseason and the upcoming campaign, next winter won’t be a vacation for the organization.

Everything that was done by John Henry, Tom Werner, Sam Kennedy, and Chaim Bloom will have massive ripple effects in the 2021 offseason. The moves they made in trading Mookie Betts and David Price, as well as, not re-signing veterans Brock Holt and Rick Porcello were all done to get below the CBT threshold.

Boston was able to accomplish that goal and currently sit under the line which will allow them to reset their penalty markers ahead of 2021. That’s when the proverbial crap will hit the fan as everything they have done to this point will have to come to fruition. Though they’ve never outright said so it feels as if these big roster moves to reset the CBT was done to make a run at Betts next year.

When you look at the calendar and next winter there are three things facing the Red Sox that they must address if they want this offseason to be a success.

The first is re-signing Betts, that is an absolute must. They reset the penalties and have the cash to splash down on the former MVP. He’s made it pretty clear what he wants and it feels like the highest bidder will get his services.

With the financials under control to some degree, there’s no reason that that bidder shouldn’t be Boston. They can essentially offer him whatever they want in relation to his asking price and do so with the least amount of repercussions.

Item number two that needs to be figured out is the playing future of J.D. Martinez. The power-hitter has opt-out options in his current contract after the 2020 and 2021 seasons. With his best friend now in Los Angeles, the likelihood of Martinez remaining with the Red Sox after this season is pretty slim.

However, if Boston sits down with J.D. and re-works his deal to eliminate those opt-outs that would be a positive step for the future. With the National League gaining the DH spot beginning in 2021, Martinez’s options and list of suitors will grow exponentially.

The Red Sox need to lock him down and keep him at Fenway Park for the foreseeable future, especially with few true DH options on the market or in- house at the moment.

Plus, there’s no way that he and Mookie don’t talk this season and discuss what their desires for the future are. We see it in sports all the time and I wouldn’t be surprised if these two don’t keep conversations running about next winter.

Finally, the third elephant in the Red Sox front office will be free agency. I know that seems like a broad, “no-duh,” statement, but hear me out. Just as I said with Mookie, the penalties are reset and the spending can once again commence. Many have cried that FSG is cheap in the wake of the Betts trade, but that’s far from the truth.

Since their arrival in Boston, FSG has supported one of the highest if not the highest payrolls in the league year after year. I hated seeing Mookie go to another team, especially the Dodgers, but it also meant getting Price’s ridiculous salary off the books. Considering this ownership group has handed over insane amounts of cash each season being a little thrifty for one year won’t be the end of the world.

By being financially responsible, FSG and Bloom will be able to spend next year without the monetary guillotine dropping on their necks. This is where free agency will once again rear its ugly head. Boston will have several free-agents next winter including Jackie Bradley Jr. and Brandon Workman. Add in recently acquired outfielder Kevin Pillar and the possibility of Martinez walking, and the Sox are in some serious trouble.

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Bloom and his squad handed out several short term deals this winter as a way to patch the gaps in the lineup for 2020. Those Band-Aids won’t last for long though as the pains of 2021 will soon be felt. Boston will need to spend and spend wisely next winter as they can get back to the American League mountaintop with a few key signings. Again, Martinez and Betts are the two major assets that the Red Sox need to get on paper.

As far as the outfield and the pitching is concerned, that may feel some growing pains. Alex Verdugo is a very talented young player but a back injury has slowed his progression. Having guys like Mookie and J.D. to put around him along with possibly extending Pillar could work wonders for the youngster.

Pitching will once again hurt Boston as they have young talent that is either not quite ready to the big leagues or is here and hasn’t found their groove. Picking up a veteran starter like Trevor Bauer or even Marcus Stroman could be good moves.

Both are still relatively young while each has great experience in the majors. If I were Bloom, I’d offer Workman an extension this season. He should’ve gotten one this past winter but with the budget how it was, it wasn’t in the cards.

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The Red Sox have a myriad of challenges in front of them but next winter feels like the biggest hurdle they’ll have to jump. Not only will they have to manage their own free agents but also the market as a whole. Then there’s the need to retain some of their best players to set the organization up for success down the road. One thing’s for sure, I sure as hell don’t want to swap chairs with Chaim Bloom anytime soon.