Andrew Benintendi agrees 5-year, $75m deal with White Sox

4:31 p.m. ET

jess rogers

CloseESPN Staff Writer Jesse joined ESPN Chicago in September 2009 and covers MLB for ESPN.com.

Jeff Passan

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Author of The Arm: Inside the Billion-Dollar Mystery of the Most Valuable Commodity in Sports

Outfielder Andrew Benintendi and the Chicago White Sox agreed on a five-year, $75 million deal on Friday, sources told ESPN, linking one of the game’s best bat-to-ball batsmen with a team whose contact-oriented approach is one of its offensive ones trademark is .

Benintendi, 28, hit .304/.373/.399 this year during his stint with the Kansas City Royals and the New York Yankees, who acquired him in a deadline trade. Benintendi, a left fielder who won Gold Glove, had the ninth-best batting average in Major League Baseball and a top 25 strikeout percentage in 2022.

The $75 million guarantee represents the largest free agent contract in White Sox history, surpassing the $73 million received by catcher Yasmani Grandal in a four-year deal that expires after the 2023 season.

The White Sox, whose disappointing 2022 was marred by injuries and setbacks, ranked 19th in the MLB in runs scored and lost their best offensive player, first baseman Jose Abreu, to the Houston Astros via free agency. Left fielder Andrew Vaughn is expected to move to first base, freeing Benintendi to join midfielder Luis Robert, one of the White Sox’s founding players.

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Chicago’s offensive talent with Benintendi, Robert, shortstop Tim Anderson, designated hitter Eloy Jimenez and third baseman Yoan Moncada runs deep enough that the White Sox are dreaming of a better performance than their 81-81 season in 2022. Manager Tony La Russa stepped in after the season, and new manager Pedro Grifol was manager at Kansas City, where Benintendi spent a season and a half after five years in Boston.

He won a World Series with the Red Sox in 2018 and in Game 4 of the American League Championship Series scored a late-game sliding catch that helped Boston beat Houston. The Red Sox picked Benintendi with the seventh pick in the 2015 draft — a pick ahead of the White Sox — and he made his debut the following season. By 2017, he was establishing himself as a potential star of the future, hitting 20 homers, stealing 20 bases and hitting base more than 35% of the time.

With a career on-base percentage of .351, Benintendi could find himself at the top of the White Sox lineup, perhaps in the No. 2 hole behind Anderson. In 745 career games, he has hit .279/.351/.431 with 73 home runs, 384 RBIs and 69 stolen bases.

The deal is expected to take the White Sox’s payroll to over $200 million for the second straight season.