We all love Randy Moss now that he's a Patriot, but for the sake of argument let's pretend that he was never traded by Oakland and played out the rest of his career there doing more-or-less what he had been doing for the Raiders in the years he was there. In that example, how many of us would consider him a HOF candidate?
If it were me I'd say "no way." I would have remembered Moss as a loudmouth who had a couple of good years in a wide-open Vikings offense, but had no meaningful playoff wins, wasn't a leader, and mostly played for crappy teams. Not nearly a HOF candidate in my book. And to top it off he'd probably be retiring around the same time as guys like Marvin Harrison, Chad Johnson, Steve Smith, Rod Smith, Tory Holt, Hines Ward, TO, and no way are all those guys making it in.
I don't think you can underestimate how huge this year playing for the Pats has been for his reputation and therefore his HOF chances. If everything goes as we hope it does, Moss will have suddenly become the leading receiver and a team-first-guy on a SB winner (knock-on-wood). I'm still not sure that GUARANTEES him a place in the HOF but it will put him pretty close.
If he wants to guarantee that spot the best way for him to do it is to re-sign with the Pats for multiple years and put up 3-4 more 1000+ yd and 10+ TD seasons while doing some damage in the playoffs. That would make him a lock. But he could still screw it up I think by taking another Oakland-type deal.
I certainly hope Moss feels that way too, because I'm betting that there is some other desperate team in the NFL willing to give him more money next year than the Pats will. If he stays it will because he feels like he has made enough money already and is thinking about the HOF, maybe a broadcasting career, and his legacy in general.
This gives us a shot, at least, of re-signing him after this season.