Red Sox

Red Sox

Of all the what-ifs related to Chris Sale, here's one Red Sox fans probably haven't considered: what if they had traded Andrew Benintendi to acquire him instead of Yoan Moncada?

White Sox GM Rick Hahn wanted star prospects when he began trade talks with Red Sox counterpart Dave Dombrowski at Scottsdale's Omni Resort during the 2016 GM Meetings. And the first name on his wish list was Benintendi.

The 21-year-old outfielder had raced to the majors a year after being drafted seventh overall out of Arkansas. He hit .295 with an .835 OPS in 34 games, sparking a run to the playoffs. He even exhibited toughness by returning to action after suffering a nasty hyperextended knee.

LIVE stream the Celtics all season and get the latest news and analysis on all of your teams from NBC Sports Boston by downloading the My Teams App.

He looked like a potential cornerstone and Dombrowski had no interest in moving him, in part because he believed Benintendi would play a bigger role for the 2017 Red Sox than Moncada. For a team with designs on contending, the immediate need in the outfield trumped whatever Moncada might provide in the future. It helped that Benintendi was clearly the more polished prospect.

Suffice to say, things have changed.

While Benintendi has mysteriously regressed over the last year and a half, Moncada is soaring. He just agreed to a five-year, $70 million extension as a foundational piece for a White Sox club that believes it's ready to contend after five years building one of baseball's best farm systems.

With Sale injured and possibly facing Tommy John, and Benintendi needing to prove that he's more than a JAG in the outfield, Moncada's emergence makes you wonder how different the Red Sox would look with an infield of Moncada at second, Rafael Devers at third, and Xander Bogaerts at short.


The White Sox originally wanted Devers, too, but the Red Sox ended up building a deal around Moncada -- whom they signed for a record $31.5 million out of Cuba in 2015 -- and right-hander Michael Kopech.

"The reality is they either wanted Benintendi or Moncada as the No. 1 guy," Dombrowski told NBC Sports Boston last August. "Now Devers' name came up after that, but it was clear that they wanted one or the other in order to start the conversation, and the next part of the conversation was Kopech.

"At one point they said they might go in a different direction if we didn't include (Devers), and we said we're just not going to give you up those three guys. But Moncada/Benintendi was always their main guy. And so once we had settled on that, even though we liked Moncada a lot, we thought Benintendi was going to be in the outfield for us that year and we were trying to win. So we didn't want to give up Moncada up, too, but you know you're going to have to give up something."

What felt like sound logic is now open to second-guessing. Benintendi is coming of a meh season that saw him hit .266 with 13 homers and a .774 OPS that is the definition of average. Moncada, meanwhile, earned MVP votes after hitting .315 with 25 homers and a .915 OPS.

After striking out a league-leading 217 times in 2018, Moncada K'd just 154 times last year by becoming more aggressive, which sounds counterintuitive, except it cut down on his strikeouts looking. He featured elite bat speed, ranking among the league leaders in average exit velocity (92.8 mph). He also thrived at third base, limiting the defensive miscues that had plagued him at second.

"He certainly improved on both facets," Sox manager Rick Renteria told the Chicago Tribune last month. "I thought his third base play was really good after transitioning from playing second base the previous year. I know everybody was concerned. He was very solid there. He went through his offensive correction in terms of strikeouts and things of that nature.

"He's a young man who has a tremendously high ceiling. He'll be able to pop a ball out of the ballpark. He's going to hit for a decent average over time, he's going to walk. There's nothing that he can't do. He's one of the five-tool players that we have on the club."

Benintendi, meanwhile, just signed a two-year, $10 million extension that means he won't have to attend an arbitration hearing next year and not much else. He faces a make-or-break season as the Red Sox try to determine if he's their leadoff hitter of the future or simply another trade chit.


Three years ago, a compelling case could've been made that Benintendi looked like the better prospect with the brighter future.

But if Chaim Bloom proposed a straight swap today, Hahn wouldn't take even his call.