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1821: The Great Hurricane
This devastating storm was the first recorded tropical cyclone to hit New York City. Storm surges created waves that reached heights of thirteen feet. All of lower Manhattan up to Canal Street was completely flooded. The storm could have been even worse if it had not struck at low tide. As it was, this hurricane was notable for being one of the only times an eye of the storm passed directly over New York Harbor, which has traditionally been protected from direct hits due to many geographical features and sheer awesomeness. Probably just the first reason, actually, because nothing stops Mother Nature once she's really out to get you. She's relentless.