Red Skull - Captain America Vol. 5 #25 (Death of Captain America Vol. 1)
Captain America Vol. 5 #25 is a comic book that is dear to my heart for one simple reason: the villain wins. Much like Darkseid in JLA: Rock of Ages, Death of Captain America (Vol. 1) sees the Red Skull triumphant over his heroic adversary. The Red Skull's years struggling with Captain America and the forces of good pay off in this book with the assassination of Steve Rogers.
This comic event takes place immediately following the events of Civil War. Steve Rogers, always driven to do "the right thing", turns himself over to S.H.I.E.L.D. agents to be put on trial for his actions. Told by reporters, Captain America's transport into New York, as well as his trial, are made public in the interest of "full transparency". A smart citizen throws a tomato at Cap while the villain Crossbones, hired by Red Skull, aims his sniper rifle. The shot hits Captain America in the back of the neck, exits through the throat, and kills him.
There are two more volumes that provide follow up for this story. They surround the Red Skull's plans to manipulate the political system and get one of his henchmen elected president. From my understanding the goal, then, is to create panic and convince citizens of the need for a privately owned military state- which will benefit the Red Skulls interests and insight fear into the hearts of the American people. The second, more disturbing, part of the plan is to rehabilitate a brainwashed Nomad and convince him that HE is Captain America. With the president and the new Captain America in his pocket, the Red Skull would be unstoppable.