Details On How Red Sox’s Three-Team Andrew Benintendi Trade Materialized

The Red Sox worked with the Royals and Mets separately

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The Boston Red Sox’s recent three-team trade involving Andrew Benintendi more or less can be dissected into two separate deals: one with the Kansas City Royals and one with the New York Mets.

That’s because, as we’ve since learned from both the Royals and Mets front offices, Boston negotiated separately with each team, first agreeing to a trade with Kansas City then flipping part of its return to New York.

As Royals assistant general manager J.J. Picollo recently explained to Boston Sports Wave’s Quinn Riley, the Red Sox brought the Mets into the mix only after working with Kansas City to acquire outfielder Franchy Cordero, outfield prospect Khalil Lee and two players to be named later in exchange for Benintendi and cash.

The Red Sox then agreed to trade Lee to the Mets for minor league pitcher Josh Winckowski and a player to be named later, ultimately creating a three-team deal that presumably satisfied all parties.

“Very candidly, that was something that the Red Sox had orchestrated themselves,” Picollo said during his interview with Boston Sports Wave. “(They) informed us about a day before the (trade) that they were probably going to trade Khalil Lee to another team, and then as we got down to the last hours before the trade was finalized, they told us that he was going to be going the New York Mets.

“So, sometimes, those three-way deals, all three teams are involved to make it work. And in this case, it was really just us and the Red Sox, and then the Red Sox trying to be creative and improve their system. They had the idea that, ‘We could maybe trade Khalil Lee and get something else that we need.’ And they flipped him to the Mets. Those deals are always interesting, and they come together in different ways.”

When the dust settled, the Red Sox wound up with five players in exchange for Benintendi: Cordero, Winckowski and three players to be named later (two from the Royals and one from the Mets).

The players to be named later are not insignificant in this particular trade, as Lee is a more renowned prospect than Winckowski. Therefore, the player to be named later that Boston ultimately receives from New York essentially will make up for the difference in value between those two farmhands.

The Red Sox evidently saw an opportunity to flip Lee to the Mets — and potentially enhance their overall return package — based on the interest New York’s acting general manager, Zack Scott, showed in the young outfielder while with Boston’s front office.

“We didn’t have direct conversations with Kansas City on that,” Scott told reporters last week, per the New York Post, regarding the Mets’ three-team trade with the Red Sox and Royals. “With my connections to Boston, quite frankly, they know that I liked Khalil Lee. They reached out and asked if there would be interest here. We were excited. Our pro scouts here really liked the player. A lot of tools and athleticism. We liked a lot of things about his performance, as well.”

So, was this an instance of Red Sox chief baseball officer Chaim Bloom turning checkers into chess?

Let’s not go that far, especially without knowing the three players to be named later, whom the Red Sox likely will receive after the minor league season begins. As Lynn Worthy of The Kansas City Star wrote last week, “Including the Mets did not alter what the Royals would give up in the deal.”

But it’s clear the Red Sox are exploring all avenues while trying to rebuild after a disappointing 2020 season. And Boston’s farm system gradually is improving as a result.

Thumbnail photo via Raj Mehta/USA TODAY Sports Images

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