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When The Time Comes, Will The Yankees Pay Aaron Judge?

Aaron Judge

Aaron Judge
When the time comes, will the Yankees pay Aaron Judge? It’s going to be the most fascinating contract negotiation in recent memory. Don’t be so sure the Yankees are willing to do so. (Adam Hunger/Associated Press)

You have to make tough decisions in baseball. The Red Sox were crushed for trading Mookie Betts. In sports, it’s all about realizing your window. The Red Sox can’t win the World Series in 2020. They decided to move on rather than pray he will stay by extending a $400 million contract. It’s also not to say they can’t re-sign him after this season. Here’s my question, when the time comes, will the Yankees pay Aaron Judge?

You sure about that Russillo? You sure that’s the stance you want to go with? The Yankees have absolutely done this. It was called Robinson Cano. The only difference is they didn’t’ get anything back for him.

No, Robinson Cano wasn’t quite as good as Mookie Betts is during his Yankee heyday. He was damn close. Cano finished in the top 5 of the American League MVP voting race his final 4 years with the Yankees. Mookie Betts never did that or even came close. Robinson Cano was a bonafide superstar and New York let him walk out the door cause they didn’t want to pay him. So don’t sit there and tell me the Yankees would never do this. It’s called Robinson Cano.

You sure the Yankees would never do this? We’re going to find out in a few years. When the time comes, will the Yankees extend Aaron Judge? It will go down as the single most complicated contract negotiation in recent memory. If Judge doesn’t take a hometown discount things will start to get dicey.

The Yankees payroll is going to become fascinating over the coming years. Judge will enter the final year of team control in 2022. New York will have over $119 million committed to 6 players excluding Judge. By this time, New York will be getting clobbered by the Luxury Tax (if CBA doesn’t change). New York was over the tax last year. This year they will exceed it by a significant number with a payroll that stands at about $246 million.

By 2022, New York will have a large payroll if they never add another contract to the books and let the expiring deals run out. We know that won’t happen. The fact of the matter is, You’re paying Gerrit Cole $36 million a year and Giancarlo Stanton $29 million a year. High arb numbers will start to come through for Gleyber Torres, Garry Sanchez, Miguel Andujar, Gio Urshela, and Aaron Judge. Again, that’s if they don’t’ add another player to the roster. Aroldis Chapman, Zack Britton, Luis Severino, and Aaron Hicks are also on the books to big money deals.

A lot can change by 2022. The fact of the matter is, the Yankees have big future financial commitments if they never do anything else to improve the roster. The problem is this is their window so they have to add to the roster to try to win now. How many more deals will they add by that period of time.

You sure the Yankees would never do this? This is the biggest road block. Judge will hit the open market at 31 because he reached the majors so late. It’s much older than other players that hit free agency. Will the Yankees pay Judge a massive contract extension knowing the future production won’t meet the past production? Will the Yankees pay Judge given the already lengthy injury history knowing those concerns may get worse as he ages? You sure the Yankees would never do this? What happens if you pay Judge and then both he and Stanton are constantly on the IL collecting checks missing 70 games a year? You sure the Yankees want to take that route?

Aaron Judge is the face of the franchise, but he’s also missed a significant number of games the last two years. That looks like it’s going to be the case in 2020 too. He’s already ruled out for opening day. Who knows what will transpire over the next two years. Regardless, the man will get paid on the open market. Judge is too good of a hitter and extremely underrated athlete in the outfield not to get his check. Someone will pay for it when the time comes. My question is will the Yankees be the team that pays it?

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