Yankees: Why Judge Should get an extension sooner, rather than later

Entering his third season with the New York Yankees, Aaron Judge has established himself as the team’s best player. Why the Yanks need to extend Judge before it’s too late.

I’m sure the New York Yankees are treading lightly on extension talks with outfielder Aaron Judge. Especially considering that their best pitcher and starting center fielder landed on the injured list (IL) a mere days after signing their own respective extensions.

Closing in on age 27, however, the Yanks should really be considering locking Aaron Judge down before it’s too late.

Fortunately for the Yankees, Aaron Judge missed becoming arbitration eligible this offseason by 83 service days. This buys the organization some time to work out a deal with Judge, who will most certainly command a pretty penny.

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In working out an extension, the organization assures a number of things. Firstly, they avoid the risk of negotiating contracts through an arbiter, who tends to land on the side of players. They can entice Judge to sacrifice a few of the years he would otherwise be a free agent in. Finally, they can make sure that the face of the franchise remains in pinstripes for as long as possible.

Aaron Judge is set to become eligible for free agency in 2023. At that point, He’ll be approaching 31 years of age, which is close to the end of a typical player’s prime. If the Yankees could convince Judge to sign an 8-year extension beginning with the 2020 season, they could potentially keep their best player for 5 years after he becomes eligible for free agency.

At that point, Judge would be 35-years-old.

At approximately $25-30M AAV, this 8-year contract would be worth somewhere around $200 – $240M. By comparison, Mike Trout will be getting $35.5M AAV until 2030. Suddenly, Judge looks like a bargain.

Not only that, by extending him so far beyond his free agent eligible years, the team also avoids negotiation long-term contracts with an aging player. Instead, they get to pay him more between ages 31-35 (when he would otherwise be a free agent) and then, depending on his performance, work out deals worth less money after that.

This, of course, doesn’t take into account what’s best for Aaron Judge. Potentially, Judge could make way more money becoming by testing arbitration and then free agency. However, if he experiences any setbacks from here to there, his value suddenly diminishes.

At the end of the day, guaranteed money is always good money. The Yankees and Aaron Judge know that which is why an extension contract should be agreed upon sooner rather than later.