3 Former Red Sox Who Will Fail Miserably With Their New Teams in 2024

2. Andrew Benintendi

A former seventh overall pick of the Red Sox in the 2015 MLB Draft, Benintendi flashed early in his time in Boston. The left fielder finished second in the 2017 American League Rookie of the Year Voting in his first full season as he slugged an impressive 20 home runs and drove in 90 runs. Benintendi spent five seasons with the Red Sox and was a member of the 2018 World Series championship team.

In February 2021, Benintendi was shipped to Kansas City as part of a package for Franchy Cordero, Josh Winckowski, and three minor league players to be named later.

Benintendi was a Gold Glove winner in his first season with the Royals and an All-Star selection in 2022. He had a fantastic year as a contact hitter in 2022, hitting .320 in 337 at-bats in Kansas City before being traded to the New York Yankees at the trade deadline. His power and run production wasn't there in 2022, but Benintendi was still able to parlay his productive contract season into a five-year, $75 million contract with the Chicago White Sox last offseason.

Much like Bogaerts, Benintendi failed to live up to expectations in his first year of a new deal on the South Side. The outfielder recorded his lowest marks in full-season batting average and RBI while equaling his full-season home run low, hitting .262 with five home runs and 45 RBI.

If he gets out to another slow start this season, Benintendi could definitely start feeling the heat from continuous underperformance on that contract.