What kind of money could Aaron Judge get now? What kind of money should Judge get now? Should he even get it now or should he have to wait?
This is where my mind headed after the big ticket free agents — Bryce Harper and Manny Machado — finally signed, and one potential free agent for next season — Nolan Arenado signed his own massive extension to stay in Colorado.
So, I began asking around, talking to several agents and executives. Before I get to what the total years and dollars could look like, let's take a look at all the factors involved.
The first thing to remember is that Judge is in a completely different situation than any of those guys above because he cannot become a free agent until after the 2022 season when he completes his age 30 season.
Judge will be arbitration eligible for the first time after this season. What does that mean for him? It means he's about to get paid (Judge has yet to make even $1 million in any of the last three seasons). Even by conservative estimates — based on Judge playing full seasons at relatively expected levels of production — my rough estimate has him earning around $50 million in his three arbitration years. And that might be a bit low.
Mookie Betts has already made $30 million ($10 million in 2018 and $20 million for this year) with one more year left in the process. Mike Trout's extension with the Angels bought up all three of his arbitration years for the amazing bargain total of $42 million. Arenado has earned four years of arbitration as a Super Two player and will total $60 million over that time.
So, let's assume for argument's sake that Judge is healthy enough to play in at least 120 games this year, continues as the same type of player he's been and hits somewhere between 30-45 home runs, which seems pretty reasonable with the rate at which he's hit so far in his career.
Now, the Yankees and Judge start to dance the dance. It's the perfect time to get into serious long-term discussions so neither side has to go through the nasty hearing process that arbitration brings.
But because Judge's service time will take him to the arbitration level, any deal would have to pay him with respect to that process. For example, if he produces the way I described above he could easily be looking at a $10 million dollar figure for the first year of arb, so even if they sign a deal that avoids arb this is going to be the rough starting point for the first year of any multi-year agreement.
And then if reasonably expected production continues, raises to $15 million then $25 million are not far-fetched. Even one down year along the way wouldn't destroy his earning power here, because his career numbers with respect to his service time would still put him in elite territory.
Something else to consider as the sides would work towards a long-term deal is how much of a consideration is the new CBA that will have to be in place after the 2021 season? How much higher will the luxury tax threshold be pushed, meaning how much more non-penalized buying power will the Yankees have? If they work towards an agreement before a new CBA is agreed upon, then both sides will be guessing how much they can push each other here.
Judge as the clear face of the franchise has some leverage, but the Yankees will also know that there is longterm value for Judge to remain a Yankee — value both now and in his post-playing days. As one agent put it, "Does he want to become a historic Yankee, maximize his off the field revenue now and after baseball, and forfeit his opportunity to be free as a relatively young player? That is HIS call."
The biggest problem becomes how far out in his free agency years are the Yankees willing to go and will that be far enough for Judge. He is only six months older than Harper, but will be four years older than Harper at the time he hits free agency. That means you can kiss 13 total years goodbye and probably 10 years too at that point. Judge's body type is a factor. While he is extraordinarily athletic, there is still not a long list of baseball players that size to bank on his ability to stay healthy into his late 30's.
Of the agents and executives I spoke with, no one suggested a deal longer than 6 years for the free agent portion of the extension (following the three years of arbitration eligibility). One agent gave did give a range of 5-7 free agent years, but that's all.
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Six years of free agency (nine years total) could be seen as a target since that would take Judge through age 36, which is exactly where the extension Aaron Hicks received takes him. Regardless of how team friendly the dollar value is on Hicks's deal, it's still predicated on the idea that the team believes he can be healthy and productive through age 36.
As another agent put it, "Many stars are paid through their age 36 season. And it is a historical fact that values of star players increase annually even in down markets."
So, let's say now it's the end of the 2019 season and the Yankees and Judge begin serious talks. Of the responses I got, I chose two proposals that I think are a pretty good indication of what a deal might look like. One comes from an agent, the other from a former GM — both came on their own with the same premise, that the best time to negotiate will be after this season to avoid the arbitration system playing out.
The agent's proposal looks like this:
2020: $10M; 2021: $15M; 2022: $25M (total $50M through arbitration years).
2023-2028: $25M AAV x 6 years (total $150M for free agent years through age 36).
Total value = 9 years, $200 million.
This agent admitted his proposal could be a tad conservative and suggested Judge's free agent years could actually price out between $32-35M quite easily. So, the total value of a deal like this could end up as high as 260 million dollars.
The former GM's proposal looks like this:
2020: $10m; 2021: $20M; 2022: $30M (total $60M through arbitration years).
2023-2027: $33M AA x 5 years (total $165M for free agent years through age 35).
Total value = 8 years, $225 million.
Another former GM offered a nearly identical proposal but with a slightly lower AAV for free agency ($30M x 5 years, for a total of 8 years, $210 million).
I find it interesting that the agent went through age 36 and was a little more conservative in dollar value compared to both former GMs, who went one less year. The extra year actually protects the club in some cases, since it spreads the money out over a longer period of time and potentially reduces the AAV (the Hicks deal for example).
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On the other hand, a third former GM — likely burned by one too many bad contracts — told me he would pay year by year through arb and then trade the player before he hit free agency. I could never be convinced that's a direction the Yankees would ever go with a player as popular as Judge.
But another agent reminded me that the Yankees didn't sign Derek Jeter long term until after he went through arbitration twice. While Jeter was only entering his age 27 season at the time he would have hit free agency, he was then signed through—you guessed it, his age 36 season.
And while the Harper, Machado, and Arenado dollars are all going to be higher because they were younger when free agent eligible, the AAV and the opportunity to market himself as a Yankee should make up the difference.
Another factor that could favor the Yankees is that by locking in Judge now, the present value of the contract could be significantly less than the total value due to inflation. If Judge were to continue on a Jeterian ride, then "it will prove to be a financial windfall to the Yankees" according to one of the agents.
So, what's the bottom line?
The Yankees and Aaron Judge know they are good for each other and a long term deal should make sense. The best time to approach it will be after this season ends and before the arbitration process unfolds.
"The longer they wait, the more pressure there is on the Yankees," one of the agents told me.
"With each passing day his leverage increases," another of the agents said. "A premium needs to paid to retain the face of the franchise and the Yankees need to embrace their incredible fortune of having a player that is an All-Star on and off the field and appears capable of gracefully following Jeter's path."
I would be surprised if either side gets far enough along in negotiations at this stage, but after this season it will be prime time to hammer out the deal that both sides want and need to get done. Call it 8 or 9 years, and somewhere in the $220-260 million range.
Make Aaron Judge the true face of the Yankees. And then pray that he doesn't get hurt.
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