NY settled with everyone except Judge, they filed for $17M and he wants $21M. I don't know if NY fully grasps that this is the rare case where they need the player more than the player needs them, give him his $21M for 2022 and offer him the 8/240 through 2030 (eek) that I arrived at above.
If you factor in that is a season before he hits the market so protection against injury/poor performance, so essentially a 9/261 deal (although probably not structured that way to keep the 2022 number down a bit), that seems quite fair at the least. Judge has played four full-length seasons plus the shortened 2020 (25-29 age) and has played 140+ games twice, he is a perennial MVP candidate when he is healthy but we all know he is not always healthy. He played 80 percent of the games in his peak athletic years, what percentage would NY get from 30-38, 70 percent? Less? It doesn't matter, Cashman has to do this and he has to do it before the season if at all possible, IMO. 8/240 plus 21 this year might be my limit though.