The Yankees might’ve made a big mistake in free agency

andrew benintendi, yankees
Aug 20, 2022; Bronx, New York, USA; New York Yankees left fielder Andrew Benintendi (18) hits a single against the Toronto Blue Jays during the first inning at Yankee Stadium. Mandatory Credit: Tom Horak-USA TODAY Sports

Most are aware that the New York Yankees have a vacant left field position heading into spring training next month. Management has already indicated they are confident in the options already on the roster, notably Oswaldo Cabrera and Aaron Hicks, but a significant upgrade isn’t out of the question. It is possible that Cashman finally executes a deal to acquire Bryan Reynolds from the Pittsburgh Pirates, but that won’t be happening unless the Pirates reduce their asking price, which is currently egregious.

However, the Yankees could’ve solved left field in free agency by spending a bit of money and locking in a long-term solution, but they elected to take a more conservative approach. That could end up being a mistake, especially since their interest was real regarding the retention of Andrew Benintendi.

According to Joel Sherman, the Yankees wanted to keep Andrew Beninteid, but they allowed him to walk for a sizeable deal, which could’ve been a mistake.

The Yankees took a risk letting Andrew Benintendi walk in free agency:

Benintendi went on to sign a five-year, $75 million deal with the Chicago White Sox. At 28 years old, he’s in the middle of his prime, offering Chicago an elite contact hitter that posted a .304 average and .373 OBP last season between the Kansas City Royals and Yankees.

The Bombers ended up giving away prospects for no reason since Benintendi ended up breaking the hamate bone in his wrist, ending his season prematurely.

Locking in Benintendi on a five-year deal certainly wasn’t general manager Brian Cashman’s preference, especially at $15 million per season. Sherman did mention that the Yankees were willing to push five years for Benintendi if they didn’t land Carlos Rodon, who signed a six-year, $162 million deal. The Yanks have been active trying to fill the field position but have taken a backseat at this point in time as we wait for spring training to roll around. Cashman has been connected to the Minnesota Twins for Max Kepler and could even consider Austin Meadows of the Detroit Tigers if they’re willing to part ways after a down year.

Nonetheless, the Yankees currently sit at $290 million in projected payroll, just $3 million shy of the third luxury tax threshold, a number they don’t want to breach. Benintendi would’ve pushed them over significantly, meaning they would’ve had to offload Aaron Hicks or Josh Donaldson to clear salary space (they should do that anyway).

For the time being, they don’t have to worry about the luxury tax situation, but letting Benintendi walk could have detrimental consequences, considering his ability to get on base and act as a lead-off man, a position the Yankees will be extremely thin at if DJ LeMahieu is forced to miss any time in 2023.

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