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OTM Roundtable: Who are you extending?

That is, in the fictional world where that’s actually your decision to make.

Toronto Blue Jays Vs. Boston Red Sox at Fenway Park Photo by Jim Davis/The Boston Globe via Getty Images

As the Red Sox look to add impact players to their roster for the 2021 season in order to get back to relevance and, hopefully, contention, they also have some decisions to make with players already on the roster. While 2020 was certainly a bad year, as we discussed earlier in the week there are building blocks here and it would make a whole lot of sense to be talking extension with at least some of them. That was the crux of my question to the staff for this week’s roundtable. If you were in charge this winter and for some unexplained reason you could only sign one player to an extension, who would it be?

Shelly Verougstraete

I’m going to go a little off script here and say Alex Verdugo. He was excellent this year at the plate (.308/.367/.478 and 126 wRC+) and in the field (91% success rate and 1 OAA). Honestly, he is what we thought Andrew Benintendi was going to be. He is only five months older than Rafael Devers with only a year of service time. He is arbitration eligible in 2022 and a free agent in 2025, so now might be the best time to sign him to a deal that would buy a few of those arb years and hopefully some free agency out as well.

Michael Walsh

I want to see Rafael Devers signed to an extension this offseason. Devers is about to enter his first year of arbitration, so extending him would mean avoiding arbitration hearings and potentially adding a couple of years to his Red Sox tenure. Alex Bregman signed a 6-year, $100 million contract the year before arbitration (one year prior to Devers’s current situation), so something in that range would make sense. Perhaps an offer like 5 years/$110 million would get the job done. Either way, the goal here should be to avoid a repeat of Mookie Betts and show a willingness to negotiate with and prioritize your star player.

Mike Carlucci

I’m going to assume someone else will sign Rafael Devers and hand an extension to Alex Verdugo. His first “season” in Boston was everything we could have hoped for with some pop, a little speed, strong defense, and exciting plate appearances. If not for the circumstances around his arrival - and empty stadiums - he’d be a fan favorite already. Turning just 25 next May, Verdugo could be signed for seven or eight years, secure his nest egg, and still, if he wants to, be a free agent in his early 30s. This past season was his second “full” season in the majors and he’s not scheduled to be a free agent until 2025, but why wait on a player whose best years are still in front of him? If Chaim Bloom puts his plans into action as we assume, the team could look very different and Verdugo could be a veteran presence. Why not get the cost certainty and plan a budget for each season ahead of time this go round?

Boston Red Sox v Miami Marlins Photo by Mark Brown/Getty Images

Jake Kostik

I figure Devers will be the popular choice for this poll, so I’ll play a little devil’s advocate, even though my answer is actually Devers. I feel like if you can manage it, an Andrew Benintendi extension makes a whole lot of sense right now. He’s coming off a career-worst season that was ended early with injury, so this is the lowest his value likely will ever be.

I don’t know what’s wrong with him, but I also believe he will be better. Eventually. Get him signed, long-term and relatively cheaply while it’s still possible, and avoid the uncertainty in future arbitration salaries and buy out a few of his free agency years.

Brady Childs

This one’s really easy for me because I’ve been pining for this since last year: Rafael Devers.

Extensions aren’t a one-way street. Devers has to want to extend and sometimes dudes just don’t want to for one reason or another. I’m not under the impression he’s in any rush since he hits arbitration this offseason, but not every extension needs to be some coup in opportunity cost. Hitters like Devers don’t grow on trees. He’s still very young, has shown improvements at third base since 2018, and can move down the defensive spectrum if need be. There’s no baseball argument against signing him that’s not couched in some broken brained efficiency theory that only serves to make RedBall SPAC more money. If you want a sustainable winner, you draft and develop good players and then sign them and keep them for a very long time. They whiffed on Mookie. They cannot whiff on Devers.

Jake Devereaux

This is a difficult question to answer. There are three clear choices for an extension in my mind:

1. Xander Bogaerts

2. Rafael Devers

3. Alex Verdugo

I’ve been on record saying that Bogaerts is not only the best player on this team, but he’s the most important part of the team’s culture and leadership structure. On the field he is always improving offensively, he plays nearly every game, and his defense is steady while not being spectacular. I believe that this deal will get done and I believe it is the most important deal to get done, however, with two years left on his deal I don’t believe that Bogaerts and his agent Scott Boras will make it a priority this winter.

The player that I feel will be most ripe for an extension is Devers who is coming off a disappointing season. After a rough first month Devers was his normal spectacular self at the plate, but defensively he showed why he keeps his fantasy owners up at night concerned about his ability to stay at third base. I think the Red Sox can use his defense as leverage to talk the player into a mutually beneficial long term deal buying out his arbitration years and a few years of free agency. I get the feeling Devers is not the type of guy you will want to be paying into his mid-30’s, but signing him to a fair market 8-10 year deal now seems like smart business. Get it done Bloom.

Bryan Joiner

If we are talking extensions — and we are talking extensions! — I’d start with Andrew Benintendi. This isn’t a joke and actually isn’t too complicated: he can’t get worse and almost certainly will get better. Do it now and he’ll be cheap enough to swallow if he somehow continues to (figuratively) eat butts and an amazing bargain and trade chip if he ceases to, you know, be bad. Given that the Sox are loaded up the middle in the minors and have a single elite-ish outfielder down there in Jarren Duran, they’re going to need the help out there, and this is a chance to save some serious money down the road. No risk it no biscuit. Bring me the biscuit.

Matt Collins

I knew I was going to agree with Jake D here, partially because I know him and also because we’ve discussed this before. Anyway, I talked about this in the building blocks post linked at the top of this page so I won’t go too deep into, but the short answer is I would go for Bogaerts. He’s the oldest player of the big three (with him, Devers and Verdugo), but he’s also currently the best, the clear leader of the team, and most important to this discussion, the closest to free agency.