Right now, the entire Red Sox offense is seemingly revolving around whether or not they’ll be able to land that late-inning reliever we all want to see them sign. It’s impossible to say from our vantage point whether or not this is seen as a big need internally in the same way it is externally. Given their current placement on the win curve and the way the back of their bullpen looks at the moment, one would have to assume it does. You know what they say about assuming, though.
Beyond the reliever search, the big storyline for the Red Sox this winter, and one that is sure to continue through the regular season, is the big names that are set to hit free agency over the next couple of years. Just over the next two years, Boston could lose Xander Bogaerts, Chris Sale, J.D. Martinez, Mookie Betts and Jackie Bradley Jr., among others. The team can afford to keep everyone, but they almost certainly won’t. That’s just reality, unfortunately. With this in mind, it makes sense for them to try and figure out some extension terms as earlier as possible to potentially save some money and also simply get one item off their to-do list.
Sure enough, they are apparently at least holding one set of conversations. According to NBC Boston’s Evan Drellich, the Red Sox have had talks about a possible extension with one player on the roster and they are expected to pick up said talks again in the near future. Unfortunately, the report isn’t clear on who the player is, though there is speculation that it could be Andrew Benintendi.
At first, it was a little surprising to see the speculation that it could be Benintendi with whom the team is discussing an extension. He is, of course, not among the names listed above who are set to hit free agency soon, and one would think the focus would be towards keeping those names before focusing on guys who are set to be around for the foreseeable future. However, as Drellich points out, there’s reason to be wary about extensions with everyone mentioned above.
Betts has never shown an eagerness to be locked up long-term, and he’s likely waiting to see what Manny Machado and Bryce Harper get before really getting serious about any discussions. Bogaerts, Martinez and Bradley are all Scott Boras clients, and while that doesn’t preclude an extension it does make it much less likely. Sale is probably the most likely to be willing to sign an extension, but given his late-season history the last few years and last season’s injury, the Red Sox may be the side that wants to wait on that one.
So, with that in mind it would make sense that it wouldn’t be one of the obvious members of the roster with whom these discussions are taking place. Plus, the Red Sox are certainly wishing they had been able to lock down some of this talent earlier, and doing so with Benintendi could be highly beneficial down the road.
Still, there are a couple of different ways at which you could look at a potential Benintendi discussion. On the one hand, it makes all the sense in the world. Again, it’s always nice to have young talent locked up, and Benintendi is one of the most exciting young players in the league. The former number one prospect in the game, he is coming off a year in which he hit .290/.336/.465 for a 122 wRC+ (meaning he was 22 percent better than average) as a 23-year-old. He has had amazing success at a young age, and there’s little reason to expect him to get worse any time soon. There’s real star potential here, and the Red Sox know that.
On the other hand, there are arguments against the idea of a Benintendi extension. We know the Red Sox are concerned with the luxury tax threshold, and putting aside whether or not they should be we have to deal with it as a real consideration. Benintendi is currently on the books for the league minimum salary and isn’t eligible for arbitration until after the 2019 season. He’s eligible for free agency following the 2022 season. Remember that luxury tax calculations are based on average annual value of long-term contracts, so if Benintendi did sign an extension his luxury tax number would jump from the league minimum up to whatever his new AAV was. Any hope they had at staying under that highest threshold this year would go out the window, and any slight hope at resetting the tax altogether next year would as well. I don’t think that should matter, but there’s a very real chance the team would. They could at least avoid that first issue, to be fair, by holding off an officially announcing the agreement until after opening day.
All in all, I think it would be tough to be disappointed if there was indeed a Benintendi extension coming. Locking up talent is always a good thing, plain and simple. It’s double true when there’s no reason to expect an extreme downturn in performance. It’s probably too early to really dive into potential terms since we don’t even know for sure that it’s Benintendi with whom they are talking, but a good recent comp would probably be Kevin Kiermaier, who signed a six-year, $53 million deal. I’d probably be looking for an agreement a bit north of that, but in that general neighborhood.