
The Boston Red Sox are set for a potentially franchise altering offseason over the next few weeks. Fresh off an unexpected postseason run that nearly culminated with a World Series appearance, the Sox have proven once again that they are one of the top teams in baseball. Making matters even more impressive, they weren’t even expected to be a playoff team coming into the season.
Armed with World Series expectations now, the team’s offseason plans should be drastically different from what they were last offseason. Instead of bringing in lower level veterans such as Kike Hernandez, Hunter Renfroe, and Garrett Richards this time around, they should be looking to pursue some of the bigger names in free agency or the trade market. It’s quite a remarkable turnaround from last year after the team finished last in the AL East.
But first, there will be some big in house decisions that need to be made. While the Sox have a good core in place, they definitely have some spots that need to be upgraded. If they didn’t they would still be playing baseball right now.
Before they find upgrades to their weak spots though, they need to figure out what they are going to do with their core that is already in place. Let’s take a look at three big decisions that the Red Sox need to make this offseason, starting with a big question mark in the starting rotation.

Boston Red Sox big decision No. 3: Should Eduardo Rodriguez be re-signed?
Eduardo Rodriguez probably didn’t have the season he envisioned in 2021. After missing the 2020 season with myocarditis, Rodriguez made a triumphant return to the mound this season. The problem was that for the most part, Rodriguez was strikingly inconsistent, and given that he is set for free agency this offseason, he may have just lost a lot of money.
The last time we saw Rodriguez pitching before this season was 2019, when he posted a 19-6 record with a 3.81 ERA and 213 strikeouts, which earned him sixth place in the American League Cy Young race. In a season where there wasn’t much going right for Boston’s pitching staff, Rodriguez was a bright spot.
Things weren’t nearly as smooth for E-Rod this season. His ERA increased by nearly a run (4.71) and he struggled to consistently get guys out. Rodriguez would occasionally show flashes of his old self throughout the season, but then follow that up with a gross outing that would halt his momentum.
So far, the front office has remained noncommittal on whether or not they would extend a qualifying offer to Rodriguez, which would come in at $18 million. The bet here is they don’t, and if they do try to come to an agreement with Rodriguez, it will be for a much lower price. Other teams probably aren’t going to offer Rodriguez $18 million a year, so it makes no sense for the Sox to do so.
The question then becomes whether or not the team even wants to re-sign Rodriguez. He’s been a valued member of the organization for the past seven years, but it may be time to move on. He struggled pretty badly this season, and the starting pitcher market could end up being quite robust, with guys like Kevin Gausman, Robbie Ray, and Noah Syndergaard potentially being available.
Boston’s starting pitching overperformed this season, but they were still a key weakness for the team down the stretch. They figure to have Chris Sale and Nathan Eovaldi leading the way next season, but afterwards there are a lot of question marks.
Figuring out whether Rodriguez fits into the picture is one of the key decisions that needs to be made this offseason. Ultimately, it wouldn’t be surprising to see the Sox move on from E-Rod here, but you never know what could happen.

Boston Red Sox big decision No. 2: Who will stick around at DH?
It feels like the Sox are going to have to end up choosing between J.D. Martinez and Kyle Schwarber as their designated hitter next season. Both players proved to be great fits in the lineup this season, but the salary cap may not allow for both players to be brought back next season. Depending on how things go, there could be a difficult decision made quite early on in free agency.
The difficulty of that decision could be reduced to nothing if Martinez decides against opting out of his current deal. Martinez could opt into the final year of the 5 year, $110 million deal he signed back in 2018, which would lock in his salary at $19.35 million for the 2022 season. However, Martinez hasn’t given any indication on what his intentions were, with the last thing he said on the matter being that he was “right in the middle” on his decision.
If he does end up opting out, then it puts Boston’s front office in a tough spot. Martinez has been the anchor of this lineup during his stay in Boston, but in terms of value beyond the plate, Schwarber offers a lot more than Martinez. Schwarber can play in the outfield and at first base as we recently saw, but he really profiles more as a designated hitter at this point, just like Martinez.
Martinez is also already 34 years old, whereas Schwarber will be just 29 by the time the 2022 season rolls around. Investing in Schwarber feels like the safer move for the future, especially given the struggles Martinez endured during the shortened 2020 season. He had a great bounce back season this year, but it proved that the end was in sight for the veteran slugger.
You could technically bring both back, but it will cost the team a lot of money that probably needs to get used on other parts of the roster. If Martinez opts in that’s a big chunk of cap space that automatically goes to him, and would change the team’s offseason plan. If not, it gives them more freedom to navigate the waters, but also increases the likelihood he wouldn’t return,
It’s a difficult call to make, especially given how productive both players were this season. There are pros and cons to both, and in terms of short-term planning, this is probably the biggest decision the team makes this offseason. In terms of long-term planning though, there is one decision that trumps all the others.

Boston Red Sox big decision No. 1: When to extend Xander Bogaerts and Rafael Devers
Really, the decision here has already been made for the Red Sox. With all the backlash received from the botched attempts to extend Mookie Betts, the team is going to extend Xander Bogaerts and Rafael Devers at some point down the line. The question becomes when.
Of the two, Bogaerts is probably the more pressing case. Bogaerts signed a 6 year, $120 million deal back in 2019, but the problem is he can opt out after this upcoming season, and has said that he plans to do so. The good news is that he is open to working on a new deal with the Red Sox, and has said that he wants to stay in Boston.
Realistically, the front office should do what they have to do in order to fix Bogaerts’ contract this offseason. You don’t want to risk it becoming a distraction during the season (not that it would), and it would be better to get the future of the team squared away while you can. Bogaerts has shown a willingness to be a bit team friendly in his deals, so there’s no sense putting it off for too long.
As for Devers, he’s still under Boston’s control for the next two seasons with arbitration. However, it appears the longer you wait on Devers, the more expensive he is going to get. Devers is still just 25 years old and hasn’t even reached the peak of his powers yet. The longer you put it off, the more damage you are doing to your team.
At this point, the future of this team revolves around Bogaerts and Devers. Sorting out their contracts with the team is the biggest decision this offseason. They are the building blocks for the next great Red Sox team, so you may as well lock them up while you can.
Dealing Betts away when he wanted an extension could have been deadly, but the team rebounded. With Bogaerts and Devers, the decision shouldn’t be too hard; give them what they want, and build a World Series contender around them.

