After a few years, Andrew Benintendi will once again play for the Sox.
Just not the Red ones in Boston.
On Friday afternoon, ESPN’s Jesse Rogers reported that Benintendi is in agreement with the Chicago White Sox on a five-year, $75M contract. It’s the largest free-agent contract in their franchise history.
Former Red Sox fan-favorite Andrew Benintendi gets historic contract from White Sox
Benintendi was the Red Sox’ first-round pick (seventh overall) in the 2015 draft. He made his debut in August 2016, and in 2017, finished runner-up to Aaron Judge for American League Rookie of the Year. By 2018, he was part of a stellar young Boston core and a World Series champion. He, Mookie Betts, and Jackie Bradley Jr. were officially one of the best outfield trios in franchise history.
What a difference four years make.
In 2019, Alex Cora decided to mess with perfection and swapped Benintendi and Betts in the lineup. Betts was a marvelous leadoff man, but in theory, hitting second, he could drive in a run to put the Sox on the board quickly, rather than simply getting on base. The only flaw in this plan was that Benintendi struggled in the leadoff spot, hitting .119/.229/.143 in 48 plate appearances as the first batter in the game. In 48 games in the leadoff spot, he collected five first-inning hits (only one double), drew five walks, and struck out 16 times.
By the end of May, Cora reversed course and put Betts back in the leadoff spot. Benintendi recovered somewhat but was never really the same; after a strong June and July, he fell apart by September.
In the shortened 2020 season, Benintendi only played 14 games for the Sox. What would turn out to be the last year of his Boston career amounted to .103/.314/.128, four hits, one double, 11 walks, and 17 strikeouts.
The following February, exactly one year after the Sox had traded Betts to the Los Angeles Dodgers, they sent Benintendi to the Kansas City Royals in exchange for Franchy Cordero, Josh Winckowski, and three players to be named later. It was a three-team trade with the Mets, so the Sox ultimately received an outfield prospect from New York and two pitching prospects from KC.
In the softer spotlight of his new team, Benintendi rebounded in 2021. Over 134 games, he slashed .276/.324/.442 with 27 doubles and 17 home runs, his highest total since 2017. He led all left-fielders in innings played and became a Gold Glove outfielder for the first time in his career.
This season, he was an All-Star for the first time, and then the Royals traded him to the New York Yankees at the deadline. Due to a puzzling injury, he only played 33 games in pinstripes, and his numbers post-trade were markedly lower than before. He also saw a dramatic drop in power this year, only hitting five home runs in 126 total games.
When Benintendi turned things around in 2021, it was easy to say that the Sox had lost the trade, and it’s still fair to say that they didn’t really “win” it; Cordero is now with the Orioles and Winckowski struggled in his rookie season. However, to declare that it was a mistake to trade Benintendi ignores how much he struggled in his final two seasons in Boston and the likelihood that he wouldn’t have rebounded the same way if the Sox had kept him. By the time he played his final game in a Red Sox uniform, it was clear he needed a change of scenery. He was struggling to hit, field, and even run the bases, and was visibly unhappy.
Had the Sox kept him, he might have gotten even worse, which wouldn’t have benefited him or the team. The remaining years of club control enabled the Sox to send him somewhere to give him a chance to turn his career around. Now, he has the richest free-agent contract in his new team’s history.
Every trade is a gamble, and in recent years the Sox have lost more than they’ve won. It doesn’t seem like a loss to have played a part in saving a young player’s career, though.