The Yankees struck out miserably in free agency filling key position

andrew benintendi, yankees
Jul 29, 2022; Bronx, New York, USA; New York Yankees left fielder Andrew Benintendi (18) hits an infield RBI single to tie the game in the eighth inning against the Kansas City Royals at Yankee Stadium. Mandatory Credit: Wendell Cruz-USA TODAY Sports

It is no secret the New York Yankees need to fill their vacant left field position; otherwise, they will be rolling with Aaron Hicks and Oswaldo Cabrera for the 2023 season. Heading into the winter months, the hope was that Cabrera would fill a super-utility role, given his excellent defense in both the outfield and infield last year.

A 44-game sample size isn’t much, but Cabrera still managed to post 13 defensive runs saved above average and have a few flashy hitting moments. His defensive energy was enough to justify giving him a crack at a starting job, but having him fill in to mitigate fatigue throughout the season might be a better way to extrapolate his value. With players like DJ LeMahieu, Harrison Bader, and even Anthony Rizzo requiring workload management, Oswaldo could come into play.

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The Yankees are fine sticking with their own players, which is risky:

With that being said, management is still keen on giving Oswaldo a chance to win the starting life field job over Hicks, who’s coming off yet another down season. At 33 years old, Hicks hit .216 with a .330 OBP last season, mashing eight homers with 40 RBIs and recording a 90 wRC+. Hicks hasn’t recorded a wRC+ over 100 since 2020, the Covid abbreviated season. He did hit .248 with a .366 OBP, including 27 homers back in 2018, but that seems like a lifetime ago.

The Yankees invested an exorbitant amount of salary space on Judge’s extension and inked Carlos Rodon to a big deal to plug a key starting rotation spot. However, they struck out big-time, filling the left field position with a free agent, despite having multiple options on the board.

General manager Brian Cashman missed out on Brandon Nimmo, Andrew Benintendi, Michael Conforto, Michael Brantley, and a myriad of other mid-tier options. The remaining free agents include Tommy Pham, David Peralta, and Jurickson Profar. There are a few other available players, but none that would give the Yankees a legitimate competitor.

Cashman is taking a “strike gold” approach:

Cashman has been busy adding minor-league contracts and spring training invites to compete, notably Willie Calhoun and Rafael Ortega. He’s hoping to strike gold on a veteran player with juice left in the tank.

Hoping to hit big on another Matt Carpenter, Clay Holmes, or even Gio Urshela is optimistic at best. The more likely scenario is that Cashman looks to trade for a competitor, giving minimal capital in the process. Max Kepler has been floated for the past few weeks, but he doesn’t move the needle that much, given his offensive profile.

Austin Meadows could be an option, coming off a season where he played in just 36 games, dealing with mental issues. Having psychological shortcomings in the Bronx might not be an ideal combination, so Meadows may not be the best choice. There have also been reports indicating that Anthony Santander could be available, and given his switch-hitting bat, there’s value to be had, despite polarizing defense.

At this point in time, the Bombers are certainly playing with fire in left field since Hicks isn’t going to turn into the 2018 version of himself, and Cabrera is still a youngster that needs significant playing time. At the very least, Cabrera is an unknown who showed flashes of potential in 2022.

The problem is: the Yankees are still being bogged down by bloated contracts like Josh Donaldson’s and even Hicks’, who is still owed $30 million over the next three seasons. The team might be far better off if Cashman could find a way to offload those deals and reallocate some salary toward an acquisition.