What Will it Take to Sign Aaron Judge?

By Cary Greene

October 12, 2022

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With the postseason finally underway and Yankees fans presently immersed in the Division series against the Guardians, it won’t be long before our attention shifts to typical offseason subjects. The Rule-5 Draft and in-house free agents are always first and foremost as teams try to build their rosters for the next season.

If the Yankees advance, they’ll live to play at least one, possibly two more series. Unfortunately, the 2022 MLB season is coming to its inevitable close. Rumblings surrounding whether or not the Yankees can re-sign Judge have persisted for some time now, so what might it take and will he sign with the Yankees?

First, let’s look at the “what will it take” piece of the equation. If we throw out the Covid-shortened 2020 season, Aaron Judge has registered five seasons in which he’s played to a contract worth a staggering $57-million in AAV, per FanGraphs "Dollars" calculation.

Granted, he’s missed 177 total games, or more than one full season, due to injuries, but his value has indeed been $57 million despite the many injuries, none of which have been red-flag type injuries by the way.

This season, Judge has been worth $91.3 million in value and considering that he made only $19 million, the Yankees enjoyed a surplus value of $72.3 million. Suffice it to say that this past April, Brian Cashman offered Judge a seven-year, $213.5 million extension, which, combined with the $17-million it offered in arbitration for this season, would have made the entire package total just over $230 million.

Boiled down to now, that would be equivalent to a team offering Judge $213.5 million for six-years. Run that over your tongue for a moment before you swallow. Are you picking up any tasting notes of “sour grapes” or bitterness caused by “cheap wood casks” or any other “low-ball flavors?” I am. Cashman was offering $30.5 million per season for seven measly years – INCLUDING the paltry $19-million Judge and the Yankees settled on for 2022. Judge was staring at a six-year offer from Brian Cashman, for an AAV commensurate to slightly more than Carlos Correa had signed for with the Twins and only half a million less than Mike Trout makes per season, but the catch was, the deal was only for six-more seasons. Cashman very clearly was uncomfortable with Judge’s injury history and he was absolutely trying to avoid signing Judge long-term. Perhaps Cashman just didn’t want to have to deal with the back end of player contract for which he believed the player in question would likely not be very productive.

Prior to what has been a truly “Ruthian” year for Judge this season, he had played four full MLB seasons (not counting 2020) and had played to an AAV of $48.35 million. Yes, yes the injuries factor in, but based on the production he did put up, that’s where the Yankees were at with Judge.

This means that the contract that Cashman offered Judge this April was downright laughable and even insulting. It wasn’t even remotely a fair or good deal. Cashman tried to swindle Aaron Judge!

Rightfully so, Judge politely declined, saying in the aftermath, “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."

Per CBS Sports, after Cashman made the Yankees offer public at a press conference, Judge said, “That's something I felt like was private between my team and the Yankees," he said -- and it then came out that he sought 9-10 years at $36 million per year, according to the New York Post.

10-years at $36-million would have amounted to a $360 million dollar contract and that was before his epic 2022 season, but now what number is the team that signs Judge looking at?

NBC Sports reporter Julia Albaba thinks Judge’s current market value this year was $37.9 million AAV. Fangraphs would say paying him that would have been a steal based on his production.

Cutting to the chase, Aaron Judge is easily going to get at least a 10-year deal worth well over $400-million. I think the conversation for teams interested in signing Judge starts at $425 million for 10-years, with an AAV of $42.5 million and given that Max Scherzer signed a MLB record AAV-deal with the Mets for $43.3 million, I think Judge will easily eclipse that deal. Therefore, I’ll predict Judge signs for $440 million over 10-years, with an AAV of $44-million.

When Brian Cashman says Aaron Judge has a pot of gold waiting for him, that’s about how much gold will be in the pot. Bidding will be fierce but only a few teams have coffers that could fund such a contract and still put a winning team on the field.

Now to close today’s conversation with the second part of the puzzle - which team will Aaron Judge sign with this offseason? He may have reached the point where he wants to live and play on the West Coast, closer to where he’s from. He grew up a Giants fan of course and he grew up in Linden, California, which is in close-enough proximity to Oracle Park, the home of the Giants.

According to a Fox Sports tweet, Judge was spotted recently wearing a sweatshirt bearing the words: New York or Nowhere.

Could that mean Judge wants to remain a Yankee? Or does it mean he might also consider playing for the Mets? At the All-Star game, Judge wasn’t willing at all to say he’d be a Yankee for life. In fact, he seemed to tip his cap when he utterly avoided answering the question. Isn’t it fairly obvious that, for the first time in his career, he’s going to engage the free agent process to its fullest? He’s certainly earned the right to do that.

The MLB CBA has exploited him for long enough, but this offseason, he’s going to make back some of the money he was worth, but never paid. Perhaps he’ll even make out well in the long run. With the amount of money that numerous teams will likely offer, at some point the free agent process for Judge will likely cease to be about the money.

Aaron Judge may instead think about quality of life, proximity to friends and family and ultimately, playing where he’s happiest. Taxes may also come into play, though this isn’t often talked about by bloggers or discussed much in the media, part of Judge’s decision will likely involve him deciding how much he’s willing to pay in state and municipality taxes in addition to the 35-plus percent tax bracket he’ll be in. Local and State taxes can take a serious amount of a star-players income.

If Judge signs with a Texas, Florida or State of Washington (Seattle) team, his state and local tax will be 0%. (yes, you read that right). The Rangers and Astros would both seem to be in on Judge and who knows, maybe the Mariners would consider doing a Robinson Cano-esque 2.0 contract.

Perhaps Judge would consider signing with an Illinois team in order to benefit from being taxed at only 3% (the city of Chicago has a 0% tax rate if he wants to live there). Could the Cubs make a splash?

Arizona has a low 4.54% tax rate and Phoenix has a 0% tax-rate, but the Diamondbacks don’t seem to spend much coin. Colorado is at 4.63% but the Rockies haven’t been known to shell out too many big contracts, Kris Bryant’s recent deal notwithstanding.

Next, Massachusetts (Boston) has a reasonable 5.3% and Georgia (Atlanta) is likewise decent at 6%. Would Judge consider signing with the Red Sox or Braves? Both would seem to covet Judge and the Red Sox have the purse strings to make a very appealing offer.

On-down-the-list we go, now on to the city with the second highest tax rate in the US - San Francisco, which has a whopping State tax of 10.55%, compounded by a brutal 1.5% City Income-Tax – both of which combine for a total levy of 12.05%.

Finally, we land on the one city that star athletes ought to avoid more than any other city in the US - New York City of course! Playing for either the Mets or the Yankees involves paying a New York State Tax of 8.97%, but then the City of New York adds the devastating 3.648% Tax that brings playing for a team in Big Apple up to the highest tax-rate in the US, at 12.618%. Considering that many of the surrounding places where star-athletes tend to want to live have absurdly high local taxes, millionaire athletes lose more gross pay playing in New York than anywhere.

If Aaron Judge does sign with the Yankees for say - $440 million, he’ll lose $55,519,200 in taxes to New York (City and State). Considering he’s going to get plenty of massive endorsement deals from all sorts of independent sponsors, no matter where he winds up signing, he could protect more than half of the taxes NY State/City or San Francisco would collect simply by signing with the Red Sox or the Cubs –or, he could protect the entire amount by signing with a team that plays in city that has no tax whatsoever. The Rangers and Astros make a ton of sense. The food is great in Texas. The weather is beautiful in Texas. The ballparks both teams play in are very nice as well.

In today’s world, $55.5+ million saved in City and State taxes over 10 years from not playing in local, politically greedy places like New York or San Francisco is a pretty substantial amount. Why would someone sign up to allow local politicians to bleed their paycheck year after year on a long term deal? There’d have to be a substantial benefit for the player otherwise, it makes little sense.

I don’t see why Judge would really, truly be interested in signing with the Yankees, unless -

1. The Yankees were willing to offset a huge portion of the taxes he’ll be subjected to or

2. He feels he could earn far more than what he’d lose in taxes through all of the special endorsements the Yankees could offer him from a brand marketing perspective. It does seem like nine out of every 10 kids in the Metro NY area own an Aaron Judge jersey these days. The Judge brand sells. How much can Judge profit from that, versus say playing for the Red Sox or Astros?

That’s a question Judge should truly investigate as he goes through the free-agent process and the answer to the question really ought to factor heavily into his ultimate decision. I think it’s safe to say that Judge could play for any team he wants to play for, he couldn’t have more leverage at this point in time.

Judge is in what I’d classify as a dream scenario, one any free-agent in baseball would love to be in. I hope he weighs his options carefully, as I’m sure he will and I hope he winds up in a good spot, playing where he wants to finish his career. If he winds up with another team besides the Yankees, so be it. Brian Cashman had his exclusive opportunity to sign him and his offer really was rather chintzy, especially considering the way Judge has performed for the Yankees and what he’s meant to the franchise.