Should the Red Sox consider trading Benintendi for Starting Pitching?

After narrowly missing out on the 2017 AL Rookie of the Year Award and the 2018 All-Star game, Andrew Benintendi looked to be cornerstone of the Red Sox for years to come. Failed experiments with Hanley Ramirez, Rusney Castillo, and Blake Swihart, followed by using stopgaps like Brock Holt and Chris Young while competing for a 2016 division crown, all culminated in Boston's LF questions being answered in the form of an above-average player who contained the potential to be much more.

Heightened expectations and a World Series hangover loomed over the young outfielder's head for all of last season. Honestly, his final 2019 stat line wasn't terrible, but the numbers fell far short of expectations. Still, it was the defending champ's first real setback, if you think about. A college star became a top 10 draft pick, rocketed through the minor leagues, and pretty much seized the starting job ever since he made his 2016 debut. Then his success continued all the way until his second full season ended in a championship. Was it fair of fans and analysts to expect a continued linear path upward? Personally, I wanted to see how he rebounded in 2020 before making any rash decisions with the talented young outfielder. I certainly thought the idea of a trade involving Benintendi and Noah Syndergaard of the Mets was a lopsided one that favored New York, especially considering the extra year of control remaining on Benny.

That was before the Mookie Betts trade sent David Price to LA and yielded Boston another, younger LH hitting corner outfielder who remains under control through the 2025 season at the earliest. That was before Chris Sale required Tommy John surgery. That was before Rick Porcello joined Syndergaard in Queens. That was before Chaim Bloom signed Kevin Pillar.

All of this is to say that circumstances have changed (considerably) over the past several months. The Red Sox current outfield isn't as good as it was with Mookie Betts, and it may be getting even thinner if Jackie Bradley Jr. leaves for another team in free agency this winter, but I think anyone who follows this team can agree that the roster has bigger issues. Specifically, there are multiple holes in the rotation, and the farm system as of today doesn't appear to be on the verge of providing reinforcements anytime soon. Revisiting the Syndergaard proposal would be ludicrous considering he, too, underwent Tommy John surgery earlier this year. However, now might be the time to re-evaluate how much Benintendi could net in a potential trade.

Why now? His metaphorical stock might have taken a hit from his relative "down" year last season, but there's no guarantee that it's ever going to fully recover. Then there's the calendar to consider; a 26-year-old who can help a team this season and beyond is more attractive than an almost 27-year-old who's 2 years removed from his best baseball with only 2 years of team control left. Furthermore, whether the universal DH is here to stay or not, National League teams are facing an unprecedented set of circumstances that may never be seen again. During the offseason (and each franchise's entire history, for that matter) every NL front office constructed a roster to best suit the National League rules which required pitchers to hit. Their offenses certainly benefit from gaining a DH, and if the universal DH is around to stay, those teams will plan accordingly in the future, but for 2020, the new rule only helps NL teams as much as their best offensive bench player can produce, in terms of an upgrade. The only notable free agency signing to occur after the announcement of the universal DH implementation in 2020 was Yasiel Puig to the Braves, which would later be voided after he tested positive for COVID. All of this is a long way of saying that weaker NL lineups who want to contend in this shortened season could immediately upgrade both their collective outfield and the DH position by acquiring a player like Benintendi before the August 31st trade deadline.

To be clear, I'm not advocating for a Benintendi trade just for the sake of making a move. I don't think he's a ticking time bomb who has peaked in terms of value, nor would I be upset if he remained with the Red Sox for years to come. Truthfully, I'd be sad to see him leave. But it probably wouldn't hurt as bad as the Mookie trade, and if the right offer comes along, Chaim Bloom should keep an open mind. Replacing one outfielder ought to be easier than replacing most of the starting rotation, and the upcoming free agent class of starting pitchers is uninspiring, to say the least.

That aforementioned "right offer" would also need to be pretty exceptional to rationalize trading a player of Benintendi's pedigree. All of his tools grade as above average, and he would instantly upgrade every single roster in the league. He's still full of potential at his age, yet he comes with the experience of making significant contributions en route to earning a World Series ring. Quite frankly, I don't think a completely healthy Noah Syndergaard is enough. If I'm Chaim Bloom, I want either an established MLB starting pitcher with multiple years of control remaining plus some prospect capital, OR multiple top prospects, one of whom profiles as starter and is knocking on MLB's door from the upper minors. If Tampa could extract Austin Meadows and Tyler Glasnow from Pittsburgh for Chris Archer under his watch, I believe Bloom can execute a move generating similar value for Benintendi.

Maybe the Braves would surrender Ian Anderson and Drew Waters for #16. Perhaps the Reds would throw in Nick Lodolo or Hunter Greene for the opportunity to flip Nick Senzel or Jesse Winker for Benny. The Diamondbacks also make sense, considering Mike Hazen was part of the front office that drafted Benintendi. All 5 of their current Top 100 MLB prospects are position players, and I doubt they'd trade either Luke Weaver or Zac Gallen after acquiring them in separate trades. Still, their outfield aside from Starling Marte is unspectacular to put it kindly, and they certainly have the prospect capital to swing a deal, so the groundwork for a possible 3-team trade appears to be in place. (Jerry Dipoto must be experiencing withdrawals after going months without making a trade, and Seattle has some interesting pitching prospects.)

I could be wrong. Bloom might be infatuated with Benintendi to the point where he's viewed as "untouchable" or the rest of the league might simply have a lower price tag assigned to Benintendi than what Bloom would consider acceptable. I just hope Bloom is at least working the phones at this point. Otherwise the path to "long-term sustainability" on the mound is going to be a painful and arduous journey.