A familiar name from recent Boston Red Sox history could soon find himself on a fifth team in just six years.
In a report published Friday, The Athletic’s Will Sammon examined the likelihood that the Chicago White Sox might trade outfielder Andrew Benintendi ahead of the July 31 trade deadline. Sammon drew a notable comparison between Benintendi’s situation and the recent high-profile trade of Rafael Devers to the San Francisco Giants.
“Devers was valuable enough that the Red Sox required the Giants to take on roughly $255 million still owed on his contract, while only taking on around $32 million of pitcher Jordan Hicks’ remaining deal,” Sammon noted.
“In contrast, the White Sox understand they don’t have the leverage to demand similar terms for their two most expensive players, outfielders Andrew Benintendi and Luis Robert Jr. Sources familiar with the team’s strategy say the White Sox are open to including cash in potential trades involving either player.
“Benintendi, now 31, could be especially difficult to trade. He’s still owed the remainder of his $16.5 million salary for this season, another $16.5 million in 2026, and $14.5 million in 2027. With his defense having declined, nearly all of his remaining value comes from his left-handed bat, which now rates around league average.”
Benintendi, drafted seventh overall by Boston in 2015, was once one of baseball’s top prospects and played a significant role on the Red Sox’s 2018 championship team. Although he showed promise early, his performance declined over his final two seasons in Boston, leading to a trade to the Kansas City Royals before the 2021 season. He then played for both the Royals and Yankees in 2022 before joining the White Sox in 2023.
Through his first two years in Chicago, Benintendi posted a .246 average with 25 home runs and a .684 OPS. As of Friday, the 30-year-old was batting .246 with seven home runs and a .753 OPS on the season.
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