Back in 2022, the New York Yankees attempted to supplement their MLB-best roster by shaking things up at the trade deadline. One of those moves featured acquiring Andrew Benintendi from the Kansas City Royals.

It was seemingly a perfect fit. The Yankees needed a left fielder and a lefty contact bat. Benintendi was both, hitting .320 and racking up 2.5 WAR across 93 games with KC. He was nothing like the player he was with the 2018 Devil Magic Red Sox, but this new version would do.

Except … it didn’t. Benintendi logged 33 underwhelming games with the Bombers before snapping his wrist by simply swinging the bat. He was ruled out for the remainder of the year, and it was like nothing ever happened. Comparatively, the Yankees got rid of Jordan Montgomery and replaced him with Frankie Montas, who made eight starts before he was essentially never seen again. Nothing worked out except when Harrison Bader saved the team in the ALDS.

When the offseason arrived, the story remained the same. The Yankees needed a left fielder. But they didn’t budge when it came to Benintendi’s market, which surprisingly ballooned despite average (at best) defense and no sign of power.

The Chicago White Sox signed him to a $75 million contract (the largest in their franchise’s history) and Yankees fans let out a sigh of relief. They still needed a left fielder, but they didn’t need to go to those lengths to acquire one. Turns out, the Yankees were right, too, because Benintendi’s time in Chicago has been nothing short of a massive letdown.

Yankees fans must be thankful team passed on signing Andrew Benintendi

Benintendi, after a -0.8 WAR campaign, just suffered a hand fracture after getting hit by a pitch at spring training. He more than likely will not be ready for Opening Day, even though he said he hopes he can be. He’ll need an entire spring’s worth of buildup in order to return to the lineup.

Across 286 games with the White Sox, Benintendi is hitting .246 with a .684 OPS and 91 OPS+. He’s accumulated -0.6 WAR, with his -2.6 dWAR representing a completely unacceptable effort. Though his power has come back a bit (54 doubles and 25 HRs), it’s hardly noticeable when you’re playing for the literal worst team in baseball history.

Would things have been this bad had Benintendi signed with the Yankees? We’d probably say “no” because he’d be surrounded by much better talent devoid of a toxic environment. The point is that Benintendi’s decline has been on full display ever since 2019, when he took a massive step back after the Red Sox’s World Series win. Boston couldn’t wait to get rid of him, either, as they traded him after the 2020 season (during which he played only 14 games). The former first-round pick went from an all-around productive lefty bat and solid defender to a one-dimensional offensive player whose fielding abilities were falling off a cliff.

It’s definitely tough to say it, but Yankees fans definitely preferred whatever happened in 2023, Alex Verdugo, and Jasson Dominguez over being stuck with an awful Benintendi contract. Nice restraint here, Mr. Cashman.