Inside The Pinstripes

After Missing on Andrew Benintendi, Yankees Must Pivot to Find Starting Left Fielder

Andrew Benintendi signed with the White Sox in free agency on Friday.

Max Goodman

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The Yankees have flashed a willingness to spend whatever it takes this offseason to get their primary targets in free agency.

New York dropped $360 million to retain superstar slugger Aaron Judge, investing another $162 million to reel in Carlos Rodón, the best starting pitcher remaining on the open market. 

When it comes to Andrew Benintendi, however, New York drew a line and refused to cross it.

Benintendi signed a five-year contract with the White Sox on Friday, departing in free agency after finishing out the 2022 season with the Yankees. ESPN’s Jesse Rogers was first to report the signing. The left-handed hitter was a trade deadline acquisition for New York this summer, an experienced asset that was a solid fit in pinstripes until he broke the hook of his hamate bone, an injury that ended his season. 

The Yankees have been vocal about their interest in bringing Benintendi back since the offseason began. During the Winter Meetings, Yankees general manager Brian Cashman made it clear that he would "love" to re-sign Benintendi this offseason. Even Benintendi hinted at a reunion at the end of the season, telling the New York Post in October that he was open to coming back this winter. 

Benintendi wound up receiving a $75 million deal from Chicago, finding some security as he enters his age-28 season. The White Sox were willing to go for a fifth year while the Yankees were not, an impasse in contract negotiations, per Jack Curry of YES Network and Brendan Kuty of NJ.com.

With Benintendi signing elsewhere, the Yankees still have a gaping hole in left field entering the 2023 season. New York has a few internal options to choose from—veteran Aaron Hicks is under contract while prospect Oswaldo Cabrera showed an ability to play left this summer—but the best available options wore a different uniform in 2022. 

Time is of the essence, though. Other outfielders like Brandon Nimmo and Japanese star Masataka Yoshida have already signed, leaving only a few free agents left (like Michael Conforto, for instance). 

New York has been exploring alternatives on the trade market as well. The Yankees checked in with the Diamondbacks this offseason about outfielders Daulton Varsho, Alek Thomas and Jake McCarthy. All-Star outfielder Bryan Reynolds recently requested a trade from the Pirates, a switch-hitting stud that has been linked to the Yankees in the past. The Twins could be willing to move one of their outfielders—like Max Kepler—this winter as well, especially after they signed ex-Yankee Joey Gallo on Friday. 

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Max Goodman
MAX GOODMAN

Max Goodman covers the New York Yankees for Sports Illustrated and FanNation. Goodman has been on the Yankees beat for three seasons. He is also the publisher of Sports Illustrated and FanNation's Jets site, Jets Country. Before starting Inside The Pinstripes, Goodman attended Northwestern University and the Medill School of Journalism. He earned his Bachelor’s Degree in Broadcast Journalism and Master’s Degree in Sports Media, graduating in 2019. At school, Goodman was an anchor and reporter with NNN SportsNight and played on the club baseball team. While at Northwestern, Goodman interned with MLB.com as an associate reporter covering the Miami Marlins. He also interned with ESPN, working as an associate reporter on Mike Greenberg's Get Up. Goodman is from New York City. He grew up in Hell's Kitchen. Follow Goodman on Twitter @MaxTGoodman. You can connect with him via email by reaching out at maxgoodmansports@gmail.com.

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