If this phrase does happen to come from "Epic Rap Battles of History: Napoleon vs. Napoleon", then it's probably interpreted like this. Horatio Nelson was an officer in the English Navy, most famous for his service during the Napoleonic Wars. A Half Nelson is a Wrestling move. The phrase "half Horatio Nelson" would be a wacky, made-up, insult to Napoleon Bonaparte.
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Horatio Walter Lonsdale died in 1919.
No, Kyle Harmon, Horatio's son doesn't die. We see by the end of the episode, "In The Wind', that he is serving in Iraq. He and Horatio speak briefly over Skype.
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There is no pirate character on The Simpsons.You're probably referring to The Sea Captain aka Captain Horatio McCallister.