Yankees: Aaron Judge’s contract demands may strap free agency spending

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Sep 22, 2022; Bronx, New York, USA; New York Yankees right fielder Aaron Judge (99) returns to the dugout after warming up in the outfield before a game against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

The Yankees are undoubtedly pursuing Aaron Judge on a monster contract extension, but there’s a real possibility that the cost hurts their ability to continue spending. Judge has already made it known that he prefers to go to a team that will get his contract out of the way and continue adding pieces this off-season in hopes of building a World Series-caliber team.

Owner Hal Steinbrenner is confident that the Yankees will retain his services, but he must be more aggressive in free agency instead of sitting idly by while others bolster their rosters. This past off-season, Steinbrenner refused to spend big on a new shortstop, but with Oswald Peraza and Anthony Volpe expected to play significant roles in 2023, he can’t hold back from boosting the team and adding elite talent.

Last year, the Yankees finished with a $264.9 million active total payroll, leaving them with about $62 million to spend this off-season if they want to hover around that number.

However, there are ways they can open up salary space, like offloading Aaron Hicks and Josh Donaldson, who will count a combined $31.5 million next season if retained. Even infielder Isiah Kiner-Falefa signed a one-year, $6 million deal, but the team could move on from him via trade in the coming months. $6 million for a player who can only play two positions in a reserve role is a bit pricey, especially with the emergence of Oswaldo Cabrera as a super-utility option.

The Yankees may be cash-strapped after Aaron Judge’s deal:

Judge’s prospective deal is expected to reach upwards of $40 million per season on an eight-year contract. That is a significant amount of money to spend, even if Steinbrenner is willing to push into the second threshold of the luxury tax, which would accrue a 42.5% tax.

If the Yankees want to continue competing financially with some of the best clubs in baseball, specifically the New York Mets and Los Angeles Dodgers, they can’t be afraid to drop the hammer.

“Judge is believed to be seeking a deal of at least eight years with an average annual value exceeding $40 million.”

Per Mark Feinsand

As aforementioned, the elevation of Peraza and Volpe will ultimately save the team tens of millions in the future, allowing them to spend elsewhere. They have multiple contracts coming off the books, specifically Donaldson and his $21 million salary.

Since Judge is 30 years old and looking for an eight-year deal, the Yankees must maximize the early portions of the extension, spending earlier to build a deeper roster.

This means they can’t wait until later on in the deal to begin adding significant talent or wait for prospects to make a bigger impact. With Judge on the West Coast enjoying a visit with the San Francisco Giants, the pressure is on for general manager Brian Cashman, who knows the clock is ticking as the winter meetings approach.

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