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Red Sox trade Andrew Benintendi to Royals in three-team deal

Andrew Benintendi is headed for Kansas City.Matthew J. Lee/Globe staff

One year to the day after the Red Sox dealt Mookie Betts to the Dodgers, the Red Sox agreed on Wednesday night to ship out another key contributor to their historic 2018 team, dealing Andrew Benintendi to the Royals in a three-way swap that also included the Mets.

The Red Sox landed power-hitting outfielder Franchy Cordero from the Royals, righthander Josh Winckowski from the Mets, and three players to be named (two from Kansas City, one from the Mets). The Mets received Royals 22-year-old minor league outfielder Khalil Lee in the deal. According to a major league source, the Sox also sent $2.8 million to Kansas City to help subsidize the $6.6 million salary owed to Benintendi in 2021.


The Sox added an unproven but enormously talented player in Cordero whom the team hopes can make a significant contribution, as well as four minor leaguers. The deal, Red Sox chief baseball officer Chaim Bloom said, represents the team’s efforts to field a competitive roster in 2021 with a stronger farm system moving forward.

“I know for our fans, this is not the first time in the last year-plus that they have seen a player that is important to them and important to the organization leave,” Bloom said, a reference to Benintendi and Betts. “I know that’s tough. I know that’s painful. We’re obviously doing what we think is right for the organization.

“[But] we felt we were able to address a number of needs. It puts us on good enough footing going forward that it was worth swallowing hard and taking that painful step of trading a player who’s really important to us and very talented.”

Andrew Benintendi was a big part of the 2018 World Series winners.Stan Grossfeld/ Globe Staff

Benintendi, the Red Sox’ first-round pick (No. 7 overall) in 2015, shot through the minor league system and arrived in the big leagues in August 2016, emerging as the potential next-in-line to the Sox’ storied left field tradition. Evaluators viewed him as a future batting champion and All-Star, resulting in his ranking as Baseball America’s No. 1 prospect in the game entering the 2017 season.


Benintendi appeared ready to follow an upward trajectory, hitting .271/.352/.424 with 20 homers and 20 steals as a rookie in 2017, and then emerging as a top-of-the-order contributor for the 2018 Red Sox, hitting .290/.366/.465 with 16 homers among his 63 extra-base hits. He also delivered standout defense in left, highlighted by his diving catch to secure the win in Game 4 of the ALCS against the Astros.

But his numbers regressed in 2019 (.266/.343/.431), as did his defense. Then, his performance cratered in 14 games in the pandemic-delayed start to the 2020 season, with Benintendi hitting .103/.314/.128 while striking out an alarming 17 times in 52 plate appearances.

That fall proved so steep that it raised questions about whether the Red Sox would trade Benintendi at a time when his value had cratered. Still, with two years before he reaches free agency, the Sox thought that Benintendi’s current value might exceed what it would be in the middle of the 2021 season or after it, even with a bounceback.

The Sox are taking a chance on a package anchored by the 26-year-old Cordero, a lefthanded-hitting outfielder with nearly unrivaled raw power who has three years of team control remaining. Cordero is capable of hitting the ball into another dimension but has yet to perform on a consistent basis over parts of four big league seasons, many of them injury-riddled. He’s been sidelined multiple times for elbow and leg injuries, and missed most of 2020 due to surgery to repair a broken hamate.


“[Cordero is a player] whose upside and whose talent is as good as anybody on the field whenever he’s on it,” said Bloom.

In 95 big league games, Cordero is a .236/.304/.443 hitter with 12 homers. He’s played all three outfield positions. His talent is dazzling, though he’s had few opportunities to display it in the big leagues.

“I love Franchy. I’d rather have him than Benintendi,” said one National League evaluator. “[Cordero is] not that far off [from a] Joey Gallo skill set.”

Franchy Cordero is headed for Boston.Charlie Riedel/Associated Press

Winckowski, 22, was a 16th-round selection of the Blue Jays in 2016 whom the Mets acquired in January as part of the return for starter Steven Matz. In 263 minor league innings (all in the lower levels), Winckowski has a 3.35 ERA with 8.1 strikeouts and 2.9 walks per nine innings. But in fall instructional league this year, the 6-foot-4-inch righthander threw in the mid- to upper-90s, featured a very promising splitter, as well as the makings of a slider that could round out a starter’s three-pitch mix.

“He’s not a finished product yet,” said Bloom. “But he has a really good chance to impact the major league staff in some capacity.”

The three players to be named are unlikely to rank among the top 10 Red Sox prospects or in the top 100 in the industry, according to a major league source, but are expected to be potential big leaguers who add depth to the farm system in need of replenishment.


The Red Sox have dismantled an outfield trio that in many ways defined the team’s fortunes in recent years. Betts and Benintendi have been dealt, while Jackie Bradley Jr. is on the open market as a free agent — a startling turn of events given the place each held in the organization for a recent title run.

“I wouldn’t have predicted it,” said general manager Brian O’Halloran. “But we are where we are and as we’ve gone along, as Chaim has talked about both following the Mookie Betts trade and again here tonight, we try to make moves that we think make sense for the club in our big-picture goals while we try to . . . compete for a championship every year.”

One year later, two-thirds of the Andrew Benintendi-Jackie Bradley Jr.-Mookie Betts outfield has left Boston.Barry Chin

It’s possible that the money that had been earmarked for Benintendi could be used to make a run at Bradley, but the Sox seem more likely to move forward with a combination of Cordero, Alex Verdugo, Hunter Renfroe, and Kiké Hernández (as well as, perhaps, another complementary outfielder) while waiting for Jarren Duran to continue his development.

“We remain hopeful that we’ll be able to find a fit with Jackie and we also recognize that that may not happen,” said Bloom, who noted that the deal didn’t “meaningfully” change the odds of a return by Bradley.


Regardless, a period of dramatic roster turnover for the Red Sox continues, as the team continues a roster overhaul that has included several players who represented longtime building blocks.

Alex Speier can be reached at Follow him @alexspeier.