andrew benintendi
Rick Scuteri-USA TODAY Sports

Aaron Judge, Anthony Rizzo, and the Yankees are getting ready for Opening Day in the Bronx against the San Francisco Giants. None of them care about what Andrew Benintendi has to say about signing with the Chicago White Sox instead of New York this past offseason. That doesn’t mean we can’t point and laugh at it, though.

The Yankees were actively pursuing the left fielder this winter before he signed with Chicago for five years and $75 million. While that left a question mark in that spot on the diamond for New York all winter, Brian Cashman clearly didn’t want to commit that much in a deal.

As with most players (like Jacob deGrom), if they get offered a life-changing amount of money, they usually take it. Being a top free-agent target means that happens no matter what. But if there’s a large discrepancy in offers, it’s hard to pass the larger one up.

Guys like Benintendi won’t come out and directly say that, which is understandable. However, he put his foot in his mouth trying to justify the decision (quote via Chicago Sun-Times):

I don’t want to seem like I’m downplaying it, but [the money] always has been a second thing to me. I want to win. I want to get another ring. I’m just battling. I’m trying to avoid this question. I know I’m going to be asked about this all the time, but nobody wants to hear an athlete talk about that. Nothing else changes in my eyes. I’m not going to treat people differently, not going to do anything different. It’s just a byproduct of all the hard work I’ve done through the years and all the help I’ve had.

It’s great Andrew Benintendi won’t treat people differently. And of course, he wants to add another World Series ring to his collection (he won his first in 2018 with the Red Sox). The White Sox should be competitive, too. But, come on, man. He’s implying that being on the White Sox gives him a better chance of winning than the Yankees.

Chicago has reached the postseason twice since 2020. They failed to get out of the first round on each occasion. And before that, the last time they reached October was in 2008. Since winning the World Series in 2005, they’ve won exactly three playoff games.

And yes, the Yankees haven’t won it all since 2009. They haven’t even been back to the Fall Classic since then. But it’s not like New York doesn’t consistently have a chance to achieve October glory. Since 2008, the Yankees have reached the postseason 11 times. That includes five ALCS appearances, with three of them happening since 2017.

It’s hard for players to answer this type of question. Of course, they want to win, but they’re also looking to take care of themselves and their family. There’s a way to sidestep it without writing a small novel to say it’s about winning and the team’s vision. Andrew Benintendi didn’t take that route.

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You can reach Matt Musico at You can follow him on Twitter: @mmusico8.



Matt Musico is an editor for ESNY. He’s been writing about baseball and the Mets for the past decade. His work has been featured on numberFire, MetsMerized Online, Bleacher Report, and Yahoo! Sports.