The idea is that the Super Bowl is an attempt to match the two best teams (or at least two of the best) in the league in the championship game. That doesn't always work out of course, but over the long haul, yeah, it's pretty reasonable. Maybe not always THE two best, but usually two OF the best.
When Montana was playing, the NFC was so dominant that the two best teams (usually like the best four teams) were all in the NFC. SF, Was, NYG, Chi - those were the powerhouses in the NFL at the time. So we can say that Brady has been to more Super Bowls than Montana, and that's true, but that's because Montana had a harder road to go to get there, and an EASIER time ONCE they got there. So if you factor in conference championships AND Super Bowls, here are their records:
Montana
- Conf Championships: 4-3
- Super Bowls: 4-0
- TOTAL: 8-3 (.727)
Brady
- Conf Championships: 8-4
- Super Bowls: 5-3
- TOTAL: 13-7 (.650)
So Montana's record is better, but Brady's totals are more impressive.
Another way to look at it is this: Montana went to the playoffs 11 seasons (9 with SF, 2 with KC). Of those 11 seasons, he won 4 Super Bowls. That means he won the Super Bowl 36% of the times he went to the playoffs. And he went to at least the Conference Championship 7 out of 11 seasons (64% of the time).
Brady has gone to the playoffs 15 seasons. Of those 15, he's won 5 Super Bowls, meaning he's won the Super Bowl 33% of the times he's gone to the playoffs. And he has gone to at least the Conference Championship 12 out of 15 seasons (80% of the time).
Look, the two greatest QBs of all time have a terrific postseason record combined:
- Brady: 27-10
- Montana: 16-7
- TOT: 43-17 (.717)
That's astounding. But even the two greatest QBs in history - with legendary coaches and franchises around them - have won just 9 Super Bowls in a combined 30 years (not counting the years they were hurt, or like when Brady was a rookie and never played).
It's supposed to be HARD to win a championship. That's why it's sooooooo sweet when you do. If the NFL was a best 2 out of 3, I think the Brady Patriots would be 7-1 in Super Bowls - losing to St. Louis, but winning the rest. But it's not. It's one-and-done, and as we've seen countless times, in a one-game scenario, quite often the lesser team and lesser QB wins. It's just a reality. And when you have two terrific teams going at it on a neutral field, it should be around 50-50, or close enough so that yeah, Brady being 5-3 is just about right.