How likely is Aaron Judge to get a better deal than what the Yankees just offered?

Before a pitch was thrown at Yankee Stadium on Friday, the stakes of the New York Yankees’ season rose dramatically. The team failed to reach an extension agreement with franchise face Aaron Judge, and GM Brian Cashman called a news conference to make the front office’s position plain.

He told reporters the Yankees offered Judge, who will turn 30 later this month, a seven-year, $213.5 million extension that would kick in for 2023. The public airing of the negotiations made for a particularly dramatic cliffhanger as the Yankees shifted from an underwhelming offseason into a suddenly anxious regular season.

Cashman and the Yankees front office have faced the relatively unfamiliar glare of skeptics after swinging a trade that enabled the Minnesota Twins to sign star shortstop Carlos Correa. (New York’s prize in that trade, Josh Donaldson, did hand the Yankees an opening day walk-off win.) The GM recently vented about the Astros’ sign-stealing scandal that may have cost the Yankees a shot at a championship, and the Judge negotiations once again betrayed some pressure building on a club unaccustomed to coming up short quite so often.

The famously tall right fielder will now, in all likelihood, play out 2022 with free agency looming. While the prospect of Judge in another uniform is growing more real, it’s far from a sure thing. For now, the cards Cashman laid on the table provide a chance to reassess where the two sides stand, and what it says about their paths forward.

Aaron Judge turned down an extension offer from the New York Yankees ahead of their opening day matchup. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
Aaron Judge turned down an extension offer from the New York Yankees ahead of their opening day matchup. (Photo by Billie Weiss/Boston Red Sox/Getty Images)

Was the Yankees’ offer to Aaron Judge reasonable?

If we include the proposed 2022 salary — $17 million, as the team has pitched in the ongoing arbitration process — the offer amounted to an eight-year deal for $230.5 million. The total average annual value would be a smidge over $28.8 million, and the free agency years given up would carry an average annual value of $30.5 million.

Superstar extensions are always tricky and usually deadline-motivated. Both the team and the player need a push to give up their leverage. For the teams, the passage of time is the biggest weapon, while a player can emphasize the prospect of the open free-agent market and the career year they could rip off to drive up their price.

Teams toss out plenty of insulting offers to excellent players as they rack up hefty arbitration salaries and get within shouting distance of free agency. Some of them even get signed. But this was not one of them. The Yankees were offering a deal that would fit in reasonably with recently accepted extensions for players of Judge’s class.

If anything, they may have exhibited a bit of deference to a star whose exit would roil a restless fan base. Judge would be 31 for the 2023 season, when an extension would really kick in. As you’ll see, that’s an uncommonly old age for a big-ticket deal these days.

Consider some recent extensions that approximate Judge’s place in the baseball landscape, listed from the low end to the top tier.

  • Matt Olson got eight years, $168 million from the Atlanta Braves this offseason, starting the deal at age 28 with two years until free agency. It amounts to a $21 million average annual value in total, $22 million during the forfeited free agent years. Judge is similarly power-focused, but has absolutely outproduced Olson over their careers thus far, and plays a slightly more demanding defensive position.

  • How about Christian Yelich? The Milwaukee Brewers outfielder signed a nine-year, $215 million deal starting at age 28 that built on a previous extension and included seven years and $182 million of new money. He signed that coming off two of the strongest seasons imaginable — leading the NL in OPS both years and winning MVP once. He had a bit less leverage than Judge does currently, as he was two seasons from hitting the open market, but he had a better track record of health at the time. All of that came out to a $26 million average annual value for seven free agent years that wouldn’t seem out of range for Judge.

  • Before his relationship with the Colorado Rockies went south, Nolan Arenado signed on for eight years and $260 million one year ahead of free agency. The deal began — you’ll never guess — in his age-28 season, and he would have hit the market ahead of his age-29 season. The free agency years carry an average annual value just over $33.4 million. This would also be a reasonable range for a Judge contract — but there are good reasons Arenado inspired more confidence. He hasn’t missed more than 12 games in a season since 2014, and he is one of the best defensive third basemen of all time, giving him a fallback skill that Judge can’t match.

What Judge’s agents sought, according to Brendan Kuty of, was a contract of at least nine years and an average salary higher than the Yankees’ $30.5 million proposal.

That level of extension would be pushing into Miguel Cabrera territory and take Judge to the doorstop of 40. The Yankees, of course, can afford virtually anything and could stand to eat a few less-than-stellar seasons at the end. There has been less “spend-whatever-it-takes” energy under Hal Steinbrenner, but Judge’s potential departure represents a far more seismic juncture than the various roads not taken.

Still, it’s true that this double whammy of high salaries and 30s-spanning length simply isn’t happening in the current baseball landscape — certainly not for players without the all-around game and seemingly age-resistant greatness of a Mike Trout or Mookie Betts. And while there’s still time for Judge’s camp to find wiggle room in the Yankees’ offer, the pages on the calendar are not flipping in Judge’s favor.

Can Aaron Judge beat Yankees offer in free agency?

Players of Aaron Judge’s caliber rarely reach free agency. Since 2017, his first full season, he ranks as the fourth-most valuable player in baseball by FanGraphs’ WAR metric. If Judge does exhaust his team control and reach free agency on time, he’d be just the second of the top 12 hitters on that list to do so.

The only member of that club right now is Anthony Rendon, who left the Washington Nationals after their 2019 World Series triumph. He secured seven years and $245 million from the Los Angeles Angels, a $35 million average annual value. It’s more than the offer Judge has on the table, but it’s a bit deceptive.

Rendon was a year younger, and there is inherent risk in waiting. Judge has managed only two full seasons in his career thus far (he even missed half of the shortened 2020 slate), and a significant injury could dent his earning potential. He’s coming off of one of those full seasons, and the offer on the table would lock in $230.5 million before another year of aging and injury opportunity. Not to beat a dead horse here, but Rendon also plays a more challenging defensive position.

And while the universal DH certainly can’t hurt, finding players with Judge’s positional profile who secured lucrative long-term investments in recent years is tough. One deal this offseason might provide a lower bound, though. The Colorado Rockies — perplexing as they are — shelled out seven years and $182 million for Kris Bryant entering his age-30 season.

The former NL MVP has not been on Judge’s level offensively in recent seasons, yet he accentuated his value by playing multiple positions. Rockies being the Rockies, though, they promptly announced he won’t be doing that anymore. If he’s actually a full-time left fielder, as they claim, then that would certainly seem like a bar Judge can clear on the market, if healthy.

So, drumroll, please ... Bryant’s average annual value comes out to $26 million, where Rendon’s was $35 million. Crunch those numbers and … yep, it averages out to $30.5 million, over seven years in each case. Which is the precise deal the Yankees offered without the stress of making it through 2022 healthy or testing the whims of the market.

It is, of course, Judge's prerogative to bet on his immense talent and set his sights on hitting the winter jackpot. It's just not at all clear that time will bring a sweeter deal than the one passed up this week.