10 Comic Book Villains Who Killed Their Greatest Rival
5. Red Skull Kills Captain America - Wolverine (Vol. 3) #72
As a symbol of the depravity and brutality of the Nazi Regime, it seemed unlikely for a whole host of reasons that the Red Skull would ever defeat Captain America.
But unlikely isn't the same as impossible, and thus the seventh part of the first Old Man Logan series saw the villain murder his longtime foe outside the wreckage of what used to be the White House, just for that extra blow to the First Avenger's pride.
After defending his country with every last drop of energy and resilience left, we see the hero laying bloody, beaten, and broken - a prime target for his archenemy to finish off.
This leads to a scene where we see the frankly emotionally scarring image of Red Skull wearing Captain America's costume, creating seemingly just to create a permanent state of horror every time you recall the series.