I'll Make This Brief

After Arod opted out of his contract in 2007 he was 32 years old and coming off of a MVP season in which he hit .314/.422/.645 and lead the league in homers (54) and RBI (156).

Derek Jeter is 37 years old coming off the worst season of his career.

These two situations aren't even close to equal and it's completely unfair to say that since the Yankees paid Arod that they "owe" it to Jeter.  

As much as the Yankees overpaid for Arod, at least he was coming off of an amazing season at a (much) younger age.  It's mildly feasible to overpay for a 32 year old who just had one of the best years of his life.  In my mind there is no sensible case that one can make to say that Jeter deserves a similar deal paying him until he's in his 40s.  If you make one mistake, you don't help yourself by making another one.

Jeter is a living legend and it would be great if he could finish his career on the Yankees but if he insists on a 4 or 5 year deal at $20+ Million then the Yankees wouldn't be wrong to let him walk, they'd actually be right.