What type of contract should we expect for Aaron Judge?

The time is coming. The Yankees’ best player of the past five seasons is only one season away from free agency. That player is Aaron Judge — but talent isn’t the only thing that Judge possesses. On top of being an all-around player, he is a polarizing superstar. He sells jerseys, brings people to the stands, and is a perfect fit for the Yankees (or any team). It would be wise for the Yankees to extend him before he approaches free agency. He is the most important player on the team and losing him would result in public strife. With that in mind, how much might it cost to retain him?

For today’s standards, Judge is a bit of a late bloomer. When we think of players who entered free agency or signed an extension in their final season of control who were bound for at least $250 million, players such as Bryce Harper, Manny Machado, Francisco Lindor, Mookie Betts, and Carlos Correa (not signed yet) come to mind. None of those players were above the age of 27 at the time when they would have been a free agent. Based on age alone, Judge may be disqualified from the mega deals we have seen in recent seasons.

There is an argument to be had that Judge belongs in that class of players when it comes to pure production, making the contract situation a bit of a head scratcher. If they aren’t the appropriate financial comparisons, then who is? In the most recent future, George Springer’s contract most accurately fits the build from what we should expect from Judge. Springer entered free agency with just over 25 fWAR. Barring any significant time missed, Judge is likely to do the same.

But at the same time, do we really think the Yankees can get away with a six-year, $150 million deal for Aaron Judge? Well yes, I personally do. While he’s had a few solid seasons since, Judge has not reproduced his 8.4 fWAR season from 2017. If he did, then there would be a different argument to be had here. In reality, he and George Springer have similar outlooks. But in case you need more than just one player as a comparison, we can jump back a few more years to when another elite outfielder entered free agency after their age 31 season.

Josh Hamilton had a similar situation to Judge, in the sense that his peak was so astronomically high and the other seasons were all a tier below the peak. Obviously Hamilton was, and always will be, managing his addiction and unfortunately that decreased his number of suitors. However, his five-year, $125 million deal was not that far off from Springer’s deal, indicating that this range is a valid expectation for Judge.

If you’re still not convinced, then I will propose a final comparison in Christian Yelich’s seven-year, $188.5 million extension which kicked in this season. That’s an average annual value of just under $27 million. It’s not the craziest contract for an age 28 player who won an MVP and back-to-back Henry Aaron awards. Even that contract doesn’t look great at this moment in time due to Yelich’s extended struggles, and that was signed before the age of 30. This length and total value is probably the ceiling for Aaron Judge even if he does produce another eight win season.

It’s a tough situation. I want Aaron Judge to get as much money as possible. His free agency will set a standard for elite 30-year-old players entering free agency after the next CBA is signed. Previous markets and contracts indicate he might not be the $200 million player we all perceive him to be.

Considering the off the field intangibles certainly elevates him, but without knowing those finances we won’t be able to validate that theory. Judge and his team probably will use it as a point of power in negotiations, but it will be extremely difficult to justify him going past the mark set by Yelich. Both sides will need to reach an agreement — neither can afford to lose the other. Let’s hope that this agreement comes before this time next year.