On October 14th, 1912 Roosevelt was to make a speech in Milwaukee, Wisconsin before 9,000 people. Unfortunately, one of those people was Schrank. Before the speech could be delivered he fired once, hitting Roosevelt right in the chest.

What Went Wrong:

Compared to everyone else on this list, Schrank was a goddamn marksman. Had he aimed a few inches to the left the bullet would have torn through Roosevelt and maybe even killed him (we emphasize “maybe”—we are talking about Teddy Roosevelt, after all).

Instead the bullet struck his breast pocket where it had to punch through Roosevelt’s one-hundred page speech and his glasses case, before lodging itself in the wall of his lung.

Among the ensuing chaos Roosevelt had two options: go to a hospital and have the wound patched up, or deliver the speech while bleeding all over the place. After opening with the line “I don’t know whether you fully understand that I have just been shot,” he gave his ninety-minute speech before conceding that maybe he should have the bullet wound checked out, you know, just in case.