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Herman lost one of his arms during the mid-1950s when, while hitch-hiking, Chief Wiggum, then a dog-catcher, knocks off his arm with his dog-catching van. He told Bart that the arm was lost by sticking it out of the window of a moving bus, which was also implied when on a bus Mrs. Krabappel said not to do it because a kid once lost an arm that way. He opened a military antiques shop.
He is a brilliant military tactician, though his sanity is somewhat questionable (Bart considered him "a little crazy", while Abraham Simpson actually said he was "out of his mind"). Herman was instrumental in Bart's victory in water balloon combat against Nelson, and the negotiation of the peace treaty between the two combatants. Herman believes piercing screams for mercy can work as his secret weapon.
He is friends with Abraham Simpson, to whom he sold a fez hat, claiming it was previously owned by Napoleon. He also claimed that he owned "the hat McKinley was shot in" (which was just Abe's hat). He also has a mysterious friend called Zed, who presumably is the same Zed as in the movie Pulp Fiction; a bisexual rapist. Herman was a member of The Stonecutters, and possibly the "No Homers" club. He was also a poker buddy of Homer Simpson.
 Criminal activities
He once sold counterfeit jeans out of the Simpsons' garage, and held Homer hostage when he stumbled upon his job. He was foiled by Marge Simpson, though he was not put in jail because the evidence was stolen by the Springfield PD.
 Secret Hobbies
He collects authentic Nazi underwear, and takes bubble baths with yellow rubber duckies.
 Behind the Laughter
Harry Shearer does an impression of George H. W. Bush for Herman's voice. Herman's facial design is modeled after the show's most prolific writer John Swartzwelder, who created the character. The writers had originally planned for Herman to give a new explanation for how he lost his arm every time he appeared. However, the second joke, involving Herman having stuck his arm in a ball return at a bowling alley, got cut, and the writers never pursued the idea thereafter.