Experts weigh in on any Benintendi trades

January 14th, 2021

By all accounts, the Red Sox appear to be ready to move outfielder , and it could happen as early as this weekend. We all know what comes next -- massive speculation as to which teams might be the best trade partners.

A group of reporters, including four who cover teams that may be in the mix, gathered to discuss where Benintendi may land.

Alyson Footer (@alysonfooter, moderator): I think a few of us were surprised to see that Andrew Benintendi was on the trading block. Ian, let’s start with you. Why do the Sox want to trade him? Are you surprised?

Ian Browne (@IanMBrowne, Red Sox beat reporter): The main reason Benintendi is on the block is that he is one of the few trade assets the Red Sox have. They don't want to trade prospects. They are trying to deepen their system. Benintendi has a very similar skill set as , which makes him a bit expendable. By trading Benintendi, they could acquire assets to fill other needs on the club. And they could easily replace Benintendi from a free-agent market strong in the outfield. For these reasons, I'm not stunned.

And also, Benny hasn't performed up to his capabilities the last two years.

Footer: Right, so if he’s really on a decline (though he’s still so young), this is the time to strike, rather than wait until his value plummets, which would happen if he has another down year. Let's have the beats weigh in. Why would your team be a decent fit? Who would they have to offer in return?

Brian McTaggart (@brianmctaggart, Astros beat reporter): It's no secret the Astros have two outfield spots to fill if they can't re-sign and . Benintendi checks several boxes for them: He plays left field, which is where Brantley played; he's still young; he has two years of control remaining; and he's a left-handed bat, which would complement the right-handers like , and .

Browne: And then if the Astros don't re-sign Brantley, enter the Red Sox. Could almost be like a sign and trade.

Anne Rogers (@anne_rogers, Cardinals beat reporter): At first glance, Benintendi jumps out as someone who fits the Cardinals' needs. They're looking for outfield production, and they would love to plug 2018 Benintendi (or even 2019 Benintendi) into their lineup. He's still young, he's relatively low-cost and he still has two years of control, which appeals to the Cardinals. His left-handed bat also fits a need in the Cardinals' lineup, especially if they decide to platoon with some of their other outfielders.

Browne: With the Cardinals, I'd imagine it depends on whether they think Benintendi's $6.6 million salary for 2021 fits in their books. They seem to have a base of young talent they could dip into to make things work.

Rogers: Absolutely. And they very much could let the young talent play another year. Give another shot, along with . But as bad as their offense has been the past two years, they need an upgrade. If that comes as a platoon outfielder with some of their other young outfielders, that's at least a different look than what we've seen the past two years.

McTaggart: The issue with the Astros re-signing Brantley is he needs to get significant at-bats at DH at this point in his career. They have a full-time DH in , so on days Brantley is lineup at DH, Alvarez would have to sit. Not ideal. Benintendi is plug and play in left field daily.

Browne: I also see Benintendi as perfect for St. Louis. He is from the Midwest. That environment would suit him better than Boston. Not sure he likes all the craziness that comes with playing in Boston. He is a shy guy.

Adam Berry (@adamdberry, Pirates beat reporter): I think the argument for the Pirates, and the only reason they've been mentioned in these rumors, is Benintendi's connection to former Red Sox/current Pirates GM Ben Cherington.

Cherington was running Boston's baseball operations department when the Red Sox drafted him seventh overall in 2015. Pittsburgh is in a rebuilding phase now, even if the club isn't using that word, but Benintendi is young enough (26 to start the season) that, if his contract were to be extended here, he'd be around when the Pirates hope to contend again in a few years. And even if that doesn't happen, the Pirates could potentially buy low on Benintendi and sell high within the next two years if he were to come to Pittsburgh and return to his 2018 form.

Martin Gallegos (@MartinJGallegos, A’s beat reporter): Based on Benintendi's numbers prior to 2020, he profiles as the type of player the A's covet -- a guy who can hit the ball to all fields, get on base at a high rate and play solid defense in their spacious outfield at the Coliseum.

The A's have also been very right-handed heavy on offense the past couple of years, and Benintendi could even that out a bit. The A's are always looking to ball on a budget, and Benintendi's $6.6 million salary next season is probably cheaper than any other upgrade they could find on the free-agent market.

Browne: I don't think Cherington is Benintendi's ex-GM most likely to make a run at Benintendi. I believe that might be Dave Dombrowski of the Phillies. He is the one who put Benintendi in the Majors for the first time and was there for Benintendi at his best. The Phillies need outfielders. Just saying.

Footer: Ian, what are the Red Sox looking for in return?

Browne: The Red Sox are looking for young pitching -- either cost-controllable at the Major League level or prospects. Pitching, pitching, more pitching. That's what this organization needs. Starting and relief. They also need a second baseman. They haven't had one since Manny Machado crippled Dustin Pedroia's left knee in 2017. They'd also like outfield prospects.

Footer: To the rest of the group: What do your teams have to offer up, based on Ian’s list?

McTaggart: The Astros have enough prospects to make a deal for a player of Benintendi's stature, though their farm system isn't what it was a few years ago thanks a series of trades (Gerrit Cole, Zack Greinke, Justin Verlander) and the promotions of Alvarez and Kyle Tucker. Still, there's enough there to get something done. A name to watch is , the Astros' top prospect for the last couple of years. He's been spinning his wheels -- injury, suspension, underperformance, no Triple-A season in 2020 -- for a few years now and has seen his star fall somewhat. But I could see the Astros including him in a deal.

Footer: I do often wonder if Astros GM James Click will be slightly less attached to Whitley than Jeff Luhnow was. I would have given up on him already.

McTaggart: Yes, Click has no attachment to Whitley whatsoever. Good point. He was drafted by the previous GM. The Astros are still in a win-now mode. They were a game away from the World Series last year. They think they can win the division and make one more run at this thing before it gets more difficult to keep the band together. I don't think Click would shy away from improving the big league club at this point with a focus on the near term.

Browne: To Brian’s point, the Red Sox proved they are willing to take on a young player who was spinning his wheels when they made the move with the Phillies last August. Chaim Bloom loves a challenge. He loves to try to get the most out of an underachiever or someone who might seem stagnated by another organization.

The “no-attachment” thing is interesting. Bloom also doesn't have the same attachment to Benintendi that Cherington or Dombrowski would if they were still running the Red Sox. Always easier to trade someone else's guy.

Gallegos: If it's pitching the Red Sox want, the A's have plenty of that to offer up. , and -- Oakland's top three pitching prospects aside from A.J. Puk -- are all considered Major League ready and could probably step into a rotation at the start of the regular season, especially Jefferies and Kaprielian, who got their feet wet with brief Major League stints last year. One of those three pitching prospects mentioned could be at the center of a trade proposal. The A's also have plenty of outfield depth knocking on the door of the Majors, with and at the top of that list.

Rogers: The Cardinals have the pitching. They're not going to be willing to give up on their top prospects for this trade, but I could see them sending a Majors-ready starter -- comes to mind -- or a reliever if they believe Benintendi can return to his 2018-19 form. They don't have a lot of depth in the second-base department, but they do have outfield prospects. comes to mind, or O'Neill. What they don't want to have happen is another Randy Arozarena or Marcell Ozuna situation -- where they send the player on their way and another team unlocks the talent. That's a big part of this offseason for the Cardinals, too.

Browne: I could see a Majors-ready starter and/or reliever plus a mid-level prospect being enough to get a deal done with the Cardinals.

Berry: Coincidentally enough, the Pirates' top two trade chips right now are probably starting pitcher and second baseman/super-utility man , both of whom would come with two years of club control. They aren't stars, but they could be good complementary players. But acquiring Benintendi alone wouldn't be a good deal for Pittsburgh in that scenario, nor would it align with the organizational focus on acquiring young talent to build up the farm system.

It's also hard to imagine the Pirates taking on his contract, with more than $6 million due this year, given the way they do business. I guess there's a scenario where it would work as part of a larger deal, with the Red Sox sending prospects back to the Pirates. But based on Ian's comments, it doesn't sound like Boston is in a hurry to ship out the kind of high-upside prospects the Pirates have been prioritizing since Cherington took over. The Pirates are in a spot where they want to add prospects, not get rid of them.

McTaggart: One thing the Astros don't have are Majors-ready starters to send off to other teams. They have some good, young arms in the rotation, but not enough to send, say , to the Red Sox and feel good about it.

Browne: The Red Sox definitely won't be trading any high-upside prospects to package along with Benintendi.

Another point I want to make because it is important is that by trading Benintendi, it increases the chances the Red Sox could bring back elite defender , who is a free agent.

Bradley, Ozuna and are the three free agents I think the Red Sox are likely to pursue if Benintendi goes. Perhaps they could even sign two of them.

Footer: Let’s look at the other side -- let’s discuss why your club should NOT trade for Benintendi.

Rogers: The financials are the biggest reason why the Cardinals wouldn't make the trade. They still haven't brought back free agents and , which is their top priority. So I'm not sure if the $6.6 million Benintendi is owed for 2021 would fit into their budget without knowing for sure whether he can right the ship once he's here.

McTaggart: Ultimately, I don't think the Astros will trade for Benintendi. That's because I think they will re-sign Brantley, who seemed to enjoy his two years in Houston and was comfortable. Plus, you know he's going to hit. No question about that. The DH conundrum with Alvarez can be sorted out later.

Berry: I think Benintendi makes the most sense as a target for a win-now team trying to buy low on a guy who could be a productive everyday outfielder, and that's just not the Pirates right now. Their focus has to be on the farm system, and it would be a strange use of resources to move players with trade value now (like Musgrove or Frazier) or long-term prospects for a risky player who probably won't be around more than two years.

Gallegos: The argument against trading for Benintendi for the A's is that their outfield situation is already crowded. , and are all locks on the roster, while the A's also really like younger close-to-ready Major League prospects Barrera, Brown and even recent Rule 5 Draft pick Ka'ai Tom.

Unless the trade to acquire Benintendi involved shedding some of that outfield depth, it wouldn't make a lot of sense to keep adding to the outfield when there are more pressing needs at shortstop and second base at the moment. Another thing to consider is what role the A's would envision for Benintendi. It would seem at his best, he's an everyday player. But with the A's, he'd likely be in a left-right platoon situation with Canha in left field. Though Canha is a free agent after this season.

Footer: Let's end this with a survey like the airlines do it. “My team is going to trade for Benintendi!” Give a number -- 1 being "not likely" and 10 being "heck yea, it's happening."

McTaggart (Astros): 6

Rogers (Cardinals): 5

Gallegos (A’s): 4

Berry (Pirates): 2, just because I'd hate to see it happen after I said 1.

Browne (Red Sox): Can I chime in and give the Phillies a 7? I love the thought of Chaim and Dave making a deal. And I just thought of how much that short fence in right field in Philly would make Benintendi a better offensive player than he's been. His power would definitely go up in Philly.