Kevin Faulk, riiiiiiiings...
Rings? So no one who played before 66 is even considered? If you count championship rings, and not just Superbowl rings, then Jim Taylor has 4 (Possibly would have had 5 except for expansion leading to him playing for the Saints). He has rings from 50% of the Superbowls that were played during his era (1 of 2).
As far as money goes, that isn't an argument based on opinion, someone can base that on fact. I'd have to think one of the o-lineman, either Faneca or Mawae with their long and elite careers have probably made the most over their time in the NFL
Money is so skewed by position, that can't really be a consideration. An O lineman like Faneca has an uphill battle to catch some of the offensive skill position players, even in a short career. JR had a 60 mil contract with 32 mil guaranteed. If Flynn just shows up for his next 2 years he'll have 15 mil over 3 seasons. If he does any good at all, that number probably at least double over the next 3.
That being said, while I think YAT and Taylor are probably the top 2 guys (the guys are legendary with pretty spectacular NFL firsts associated with them), Faneca and Faulk are also in the mix for the top 5 with Faneca possibly being the best Tiger at his position ever in the NFL IMO.