Re: How will posterity remember Peyton?
Peyton is a great regular season quarterback. He'll win you games and win division titles, but he won't win you playoff games. 8 one-and-dones in the playoffs is bad. If his name wasn't Peyton Manning, we'd look at that stat and say 'average quarterback'. Sure, he's been to 20 playoff games - that's great. Winning 9 of them isn't.
One of the arguments that was just erased in this postseason was 'If Peyton had a defense like the Steelers, he'd have 5 rings!'. I'd argue against that point until I was blue in the face and often times, my friends who are Peyton and/or Indy fans would be flustered too. It would get heated by the end of it, but these playoffs just erased that point. The Broncos had a top 5 defense and a top 5 offense. His defense was playing stout football and were arguably the best defense left in the playoffs at that point. What happened, though? Peyton did as Peyton does and came up un-clutch in the playoffs. The simple fact of the matter is, Peyton Manning isn't that great when it matters most.
One of the biggest boosts that Brady has is, who did he win a Super Bowl with? Can you name a receiver that Brady won with? He was able to put up ridiculous numbers and play at such a high level without any true supporting cast. He made those receivers who they were and took a bunch of no-names to the Super Bowl and won. Three times. Peyton had Reggie. Montana had Rice. Brady had ... Givens? Branch?
Brady has always been and will always be the better Quarterback. Peyton should be remembered as the guy who couldn't get it done when games actually mattered, but he won't be.