All season long, the 2023 Yankees desperately needed a left fielder. What they didn't need, though, was Andrew Benintendi.
Often lost in Brian Cashman's failed 2022 trade deadline blunders due to Degree of Blundering, Benintendi represented yet another addition who didn't make it all the way to the finish line. A freak accident robbed Benintendi of Sept. and Oct. 2022, just as he was finally getting into a rhythm. Not only did he fracture a tiny bone in his wrist and never return, but he fractured a tiny bone in his wrist that he'd already had removed during his freshman year of college at Arkansas. Either the doctor was clueless, or the bone grew back. Only the New York Yankees could make a trade deadline addition who regenerates problematic bones in secret.
Considering the Yankees never really got to watch Benintendi fulfill his potential as a pesky contact bat/agitator/don't ask about his throwing arm, it seemed fair to want him to return on a three-year deal this offseason. After all, Cashman doesn't usually trade for players he doesn't at least try to extend down the line.
Then the Chicago White Sox came calling, blowing down the doors with a five-year, $75 million offer that represents the largest commitment to a free agent in their franchise's history. The Yankees said, "Good luck with all that," then watched Jasson Dominguez match Benintendi's WAR for the year in less than a week.
Yankees need flexibility in outfield, not Andrew Benintendi contract
Even if Benintendi would've been a better left field caretaker this year than the likes of Jake Bauers and Billy McKinney (counterpoint: would he have been?), committing to even three years of the veteran, let alone five, would feel like another foolhardy step in the Yankees' recent tradition of prioritizing somebody else's vets over their own farm.
Who knows where New York would've been if they'd started Everson Pereira earlier, or if Dominguez had starred in May rather than July? Who knows where they would've been if they'd added any number of veteran outfielders on short-term deals, rather than handing the keys to Oswaldo Cabrera and filling in replacement-level options as the season went along?
Both of these simulations will always live in the Land of the Unknown. "Signing Benintendi to a Five-Year Deal," though, is a fully known evil. That would've been brutal, and would've blocked the Kids, the Future Kids (like Spencer Jones), and any hope of a Juan Soto trade/signing.