By 1999, he had retired having won two Super Bowls in his final two seasons. Now he's the Broncos general manager.
Manning, of course, has won a Super Bowl. But just one. When the assembled talking heads of football wisdom gather Sunday mornings to grant and withdraw immortality to today's players, Manning almost always comes second when talk turns to quarterbacks. Tom Brady has three Super Bowl wins, the argument inevitably goes. Even Manning's kid brother, Eli, now has two.
If Manning could pull an Elway, the entire conversation would change. Manning, of course, probably doesn't care much about "the conversation." He would, however, care deeply about the shiny trophy.
So, in the end, who understands better how to do what John Elway did than John Elway? In Denver, Manning is allying himself with perhaps the only person in pro football management who knows what it is like to be Peyton Manning.
There are other factors, too.
Manning is a lunch-pail football player – a fact often overshadowed by his cerebral take on the game. He is a worker, and likes a workplace filled with workers and lacking in drama. In Broncos head coach John Fox, he has one of pro football's wiser heads, who's been around, seen everything, and knows how to run a tight ship without becoming William Bligh.
Perhaps even more to the point, Fox has shown himself to be adaptable. Last season, the Broncos essentially keelhauled their entire offensive philosophy when Tim Tebow became the starting quarterback – designing a new system from scratch that would fit his skill set.
With Manning, the skill set will change again – and dramatically. Tebow's boiled down run-first system will have to change to a system of countless permutations that Manning can change at will – linemen, receivers, backs, and coaches, all waiting for Manning to marshal the offense moment by moment, conductor-like, from the pit that is his spot behind center.