Peyton Manning
Yes, Peyton Manning finished his eventual Hall of Fame career with two Super Bowl wins. But those two wins shouldn’t overshadow the years upon years of postseason shortcomings endured by Manning. Despite setting an uncountable number of passing records during his 17-year NFL career, Manning was first tormented by the New England Patriots during the early 2000’s, getting sent home early virtually every year by them.
However, there was a time when Manning could have overtaken Tom Brady in the conversation for greatest quarterback of all time. But, his “pick-6” interception that led to the New Orleans Saints win in Super Bowl XLIV, and the egregious no-show XLVIII (after Manning shattered passing records as the quarterback of the Denver Broncos) are two major blemishes that limit him from ever earning such a mantle.