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What would be the next step after an Andrew Benintendi trade?

It would leave an even bigger hole in the outfield.

Baltimore Orioles v Boston Red Sox Photo by Billie Weiss/Boston Red Sox/Getty Images

Heading into the offseason, we thought the Red Sox could be ripe for a lot of trade talks given both Chaim Bloom’s experience in Tampa, who have long been one of the more prolific organizations in terms of trades, as well as how much turnover was going to be needed for Boston. To this point that hasn’t been the case, though the same can largely be said about the whole league, not just the Red Sox. Over the weekend, however, we got some news that could change this reality relatively soon. It’s not a guarantee and it doesn’t appear anything is super close at this point, but according to a report from Jim Bowden the Red Sox have had “serious” talks involving a trade of Andrew Benintendi.

This is clearly a big deal, as Benintendi is a former number one prospect in all of baseball and has been the team’s left fielder since 2017. He’s coming off a terrible 2020 that was shortened by injury, but as of now he is penciled in as a starter for 2021. The idea of trading him is a tough one to judge on its face at this point in the rumors. Benintendi, who has been largely average at the plate dating all the way back to the halfway point in 2018, certainly shouldn’t be untouchable, but it’s also hard to see his value getting lower than it is right now. There is a real fear of selling low here, but the fact is it’s only selling low if there is a bounce back coming from the outfielder. There is reason to be optimistic he will bounce back based largely on pedigree and natural talent, but it’s far from a guarantee.

Ultimately, I just can’t really bring myself to judge the idea at this point because I don’t have even a rough idea of what the return would look like. A big part of me finds it difficult to believe they’ll be able to get the kind of value back I’d need to make a deal, but that’s based on little beyond gut feel and instinct. So, we’ll save that kind of analysis for another day. Today, I’m interested in what happens if a deal actually does go down. What would be the next steps?

Even as of today with Benintendi still on the roster, the Red Sox need an outfielder and most likely a center fielder. If he were to be traded, they would almost certainly need to go out and add two. With Benintendi off the roster, they would be left with just Alex Verdugo and Hunter Renfroe as potential full-time outfielders, with players like J.D. Martinez, Marcus Wilson, Michael Chavis and Yairo Muñoz able to fill in at times but really not people you’d like to see as full-time starters to begin the year.

Tampa Bay Rays v Boston Red Sox Photo by Billie Weiss/Boston Red Sox/Getty Images

Now, part of this discussion reminds me a bit of the Mookie Betts trade talks from last winter. Don’t worry, I’m not re-litigating that whole mess nor am I comparing this situation to that. I only mean that we spent a fairly significant amount of energy trying to figure out who they would bring in to play right field after Betts was on another team, and it turns out they just got the replacement back in Verdugo as part of the trade. That could very well happen here as well, with Bowden indicating that they are looking for “prospect types” both among pitchers and outfielders.

So they could take care of one of those needs in the hypothetical trade and it would be ideal if they got a center fielder. Jackie Bradley Jr. remains a strong fit for a return, but the options beyond him are rough for different reasons and I am still pessimistic they work something out with Bradley. Getting a center fielder you could plug into the lineup right away back in a trade would be best, though I’m not sure how realistic that is. Again, it’s very difficult to gauge Benintendi’s value at this point.

It would be easier if they got an outfielder back, but what if they don’t? What if they get pitching back and/or prospects who are not major-league ready? It’s certainly not impossible to see one of those kinds of deals being worth it, but it leaves a lot of work to do in the outfield. For the center field part of it all, nothing would really change. They’d have the option of using Alex Verdugo out there in their back pocket, though I imagine they’d still prefer a more natural center fielder. That means Bradley still as Plan A, with Kevin Pillar the likeliest Plan B.

The left field situation would then become much more interesting, though. I’ve said since the start of the offseason that this part of the free agent market is the strongest, but it’s a tough fit for Boston with Benintendi in town. If they do pull off a trade, they’d have plenty of options to replace him. Marcell Ozuna isn’t a great defensive player these days, but the bat would more than make up for that and the offense would be instantly improved without having to give up a draft pick.

A slight tick down, Michael Brantley would probably be my favorite option as a steady veteran who you can plug in in the fifth spot in the lineup every day. Those are the top two, but even beyond them there are guys like Eddie Rosario or Joc Pederson or Nomar Mazara or Adam Duvall, among others. And all but Ozuna and Duvall are lefties there, leaving open a platoon role for Renfroe, who could also form a platoon of sorts with Bradley if that deal were to get done.

To me, however, the most intriguing next move wouldn’t be in free agency, but rather back on the trade market. Earlier in the winter, a report came out that the Red Sox had spoken with the Cubs previously regarding a potential Kris Bryant trade. The former MVP is heading toward his final year before free agency, and the Cubs have been rumored to be shopping him for months now. He is still presumably on the block, with Chicago having already given away Yu Darvish and non-tendering Kyle Schwarber. Bryant would be able to slide into left field for Boston, and likely wouldn’t cost much in terms of prospects since he has only one year remaining on his contract, his expected 2021 salary is relatively high, and he’s coming off a terrible 2020.

This would be an ultimate buy-low move for Boston from a team that desperately wants to offload salary, and an opportunity for the Red Sox to get a 29-year-old former MVP whose swing theoretically fits perfectly at Fenway. Remember, besides the weird 2020 Bryant has never had a wRC+ lower than 125 and has a career mark of 136. For context, Rafael Devers has never had a single season with a mark that high. The Red Sox would then, in the case of a bounce-back from Bryant, potentially have the inside track at a long-term deal before he hit free agency and/or a chance at a compensation pick if he did leave on the open market.

Then, there’s the Jarren Duran of it all. Duran throws a really interesting wrench with everything to do with the outfield, because it’s such an unprecedented situation with prospects right now. It’s not much of a secret that the organization really likes Duran as a player and believes he can make an impact at some point. The timeline is still a mystery, though. How much do you judge his strong performance at the Alternate Site this past summer? Yes, he was great against ostensibly major-league caliber pitching, but it was also not a real game environment and he was basically facing the same guys every time out. I bring him up only because, while I think he is still part of the plans, I certainly don’t expect him to be an option right off the bat for 2021, and really think he’s more part of the 2022 plans with a potential call up to come off the bench later in the upcoming season. He’s sure to be part of the conversation for those of us outside the organization if Benintendi were to be dealt, but I’m not sure how much he’d be part of the internal short-term conversation.

But more immediately, the Benintendi trade could potentially open a lot of doors. Again, the merits of trading him in the first place really comes down to how teams value him and that is really difficult to parse at this point. He’s definitely not as bad as 2020, so selling low is an issue, but teams are smarter than just looking at his 2020 at face value. If we assume a trade comes in at fair value, all of a sudden the Red Sox could have potentially helped out their pitching and/or farm system, and in the same process can swing a deal for one of the many available left fielders, of whom Kris Bryant is my personal favorite. A trade actually needs to get done first before we can have this conversation in less of an abstract fashion, but upon a quick look there is a way to make this kind of move a net positive.