4. Peyton Manning
Truthfully, Peyton Manning comes across as one of the consummate good guys in NFL history. From his teammates’ tales, to Peyton’s places on NFL Network where he visits Hall of Famers from each team, to his comedic commercials and SNL hosting throughout the years, Manning has cultivated a larger-than-life personality that is universally admired. I’ll be honest, as a fan of football in general, he’s one of my favorite football icons of this past generation.
Still, he inflicted a significant amount of pain on the Kansas City Chiefs franchise. In both his time as an Indianapolis Colt and subsequently with the Denver Broncos, Manning consistently dominated the Chiefs or simply stood in the way of playoff berths.
Though he played far more seasons for the Colts, he still easily falls on this list having smashed the Chiefs a number of times in his four seasons with the Broncos. During his tenure, Chiefs Kingdom even had to stomach another Super Bowl victory for their orange and navy blue nemesis.
Arguably the sweetest element of Peyton Manning’s time with the Broncos came in his final season with the team, and his final contest against the Kansas City Chiefs. In that game, on November 15th, 2015, Peyton Manning seemingly fell apart.
In just the first half he threw an impressive four interceptions en route to his benching in favor of Brock Osweiler. While the Broncos still went on to win the Super Bowl that season, this contest in hindsight looks to be the unofficial end of their reign of dominance. The Chiefs have won the AFC West in every season since, and the Broncos have yet to make the playoffs.
Following his retirement, it’s easy to root for a person like Peyton Manning. Even so, he was a particular pain for Chiefs Kingdom during his time with the Broncos and that is enough to place him on the list.