Andrew Benintendi is leaving the New York Yankees in free agency and joining the Chicago White Sox on a five-year, $75 million contract. ESPN's Jesse Rogers first reported the five-year agreement, with The Athletic's Ken Rosenthal reporting the $75 million figure. This is the largest free agent contract in White Sox history in terms of total guaranteed money, per The Athletic's James Fegan.

The White Sox had been rather quiet in free agency up to this point, and this is a notable move to lure Benintendi away from the Bronx. Chicago is coming off an extremely disappointing season in which it went 81-81 despite entering the season with World Series expectations, with Tony La Russa ultimately stepping away as manager. The roster clearly needed help in the outfield, and this is a move made to address that.

The Yankees acquired Andrew Benintendi in a trade with the Kansas City Royals during the 2022 season in an attempt to bolster their lineup for a World Series run. His numbers took a dip after his trade from the Royals (he made his first All-Star Game) to the Yankees, going from .320 in Kansas City to .254 in 114 at-bats with New York. He did deal with a wrist injury that wound up keeping him out of the playoffs, which saw the Yankees go to the ALCS before losing to the Houston Astros.

The White Sox would love to see Benintendi's power come back during this contract. While never a big bopper, he hit 20 home runs in 2017 as a member of the Boston Red Sox and had three other seasons with the Red Sox with at least 13 dingers, including 16 in 2018 when they won the World Series. He also hit 17 home runs with the Royals in 2021 and won a Gold Glove that year. Last season, however, he hit just five home runs total between his time with the Royals and Yankees.

This Andrew Benintendi deal comes on the heels of New York giving Carlos Rodon a huge contract in free agency. There were reports that the Yankees wanted to bring Benintendi back, but they likely weren't willing to offer what the White Sox did.