Brady vs. Montana

Montana no contest.

The case for Brady:  more Super Bowl appearances and less talent surrounding him, playing in a more difficult era.

The case for Montana:  More rings.  Higher win percentage.  Better performances in big games.  Playing career much shorter.

A couple of details -- true, Montana had a fantastic supporting cast in 1984, 88, and 89, but in 1981 he did not.  He still won.  Montana played in an era of other very strong teams - 1985 Bears and the Bill Parcell's Giants, so while Brady played in the "parity" era, Montana had some super teams to contend with.  But...the most important details to me:  Montana won those games for the Niners.  Often, in the big time Patriot wins, the victories were a little flukie - how many times did Adam Vinatieri make a freak field goal?  The tuck rule game?  Montana wins were Joe driving down the Niners to score touchdowns with little or no time left on the clock.  The fact that Brady's career has gone longer is a double edged sword (due to better medical care, diet, etc) -- he has more Super Bowl appearances, but has also looked shaky and not played his best football at all times.  Maybe Montana sticks around longer and we see him fade or lose the magic or just get unlucky.  But that didn't happen -- so pound for pound -- era for era, I'd say Montana, no question.  This is GPA, not an accumulation.