Aaron Judge contract: Predicting what kind of deal Yankees star will get in free

It would be difficult to have a better contract year than Aaron Judge. The New York Yankees star and AL MVP frontrunner is putting the finishing touches on a historic season, one that has him chasing a Triple Crown as well as Roger Maris’ American League single-season home run record, and he’s doing it right before free agency. Judge has set himself up for a massive, massive payday.

“Very few people get this opportunity to talk extension. Me getting this opportunity is something special and I appreciate the Yankees wanting to do that,” Judge said after rejecting a seven-year, $213.5 million extension in spring training. “But I don’t mind going into free agency … At the end of this year, I’ll talk to 30 teams. The Yankees will be one of those teams.”

We know the Yankees offered seven years and $213.5 million because GM Brian Cashman took the unusual step of announcing the offer terms during a press conference. Judge didn’t seem to appreciate that — “That’s something I felt like was private between my team and the Yankees,” he said — and he sought 9-10 years at $36 million per year, according to the New York Post.

The Yankees made a reasonable offer in spring training and now, nearly six months later, Judge has done what once seemed impossible: he’s earned himself more money. Teams pay for future performance, not past performance, though Judge has raised his perceived ceiling this year. No longer is he capable of “just” MVP-caliber seasons. He’s capable of historic greatness.

“We think Aaron Judge is an all-time Yankee. We think he’s a great player, beyond a great player. We think he’s a great person. That’s why we offered him the highest position player contract in the history of the Yankees,” Yankees president Randy Levine said earlier this month. “I admire him that he went out and took this upon his shoulders and we’ll sit down with him and hopefully figure it out. I think there’s no question we want him back and no question we value him.”

What has Judge’s season done for his earning potential? Well, a lot. We know that much. Let’s try to figure out what Judge’s next contract could look like after the season he’s having.

The extension offer, in context

The Yankees did not pull seven years and $213.5 million out of thin air. The extension would have begun in 2023 and the $30.5 million average annual value would have been the second richest ever for an outfielder, just above Mookie Betts and well below Mike Trout. Here are the richest outfield contracts in history:

The Yankees and Judge nearly went to an arbitration hearing this year (the two sides settled on a $19 million salary, the midpoint of their $21 million and $17 million filing figures) and, according to the New York Post, the Yankees were willing to give Judge the $21 million salary he sought in 2022 as part of the extension. The total package was eight years and $234.5 million.

All told, the Yankees offered to make Judge the second-highest-paid outfielder ever in terms of annual salary, and also give him the fifth-largest guarantee ever given to an outfielder. That said, neither the annual value nor the total guarantee would have been the richest in franchise history. Those belong to Gerrit Cole ($36 million annually and $324 million total). Also, Judge would have beaten Alex Rodriguez’s 2008-17 contract in annual salary ($27.5 million) but not total guarantee ($275 million).

So, the Yankees did offer to make Judge one of the highest-paid outfielders in baseball, but they stopped short of making him the highest-paid Yankee, either on an annual basis or in terms of total dollars. He would have still been looking up at Cole despite being a homegrown superstar. 

Contract length

Two things hold back Judge’s earning potential: his age and his injury history. Judge will turn 31 shortly after Opening Day 2023, so, in all likelihood, his next contract will buy decline years in bulk. That’s usually how it goes with long-term deals. Teams accept the bad years at the end for the elite years up front, and Judge is the best hitter in the sport right now.

As for the durability concerns, a variety of injuries limited Judge to 242 of 384 possible regular season games from 2018-20, or 63 percent. But aside from a 10-day COVID list stint last August, Judge has been perfectly healthy…