I will read John Winthrop‘s Model of Christian Charity against and through Edgar Allan Poe‘s poem ‘The City in the Sea’. Winthrop and Poe both localize a ‘city’ to represent an extreme form of society. The koine Greek of Matthew 5 uses the word polis to describe a ‘city on a hill’. Christ says this city must not be hidden, but rather should shine so that the world may see it. The New Testament‘s merging of ‘politics’ and ‘city’ in the word polis makes it unsurprising that many Anglophone writers invoke ‘city’ in a title or phrase when making political innuendoes. Winthrop was a devotee of scripture, and Poe knew Greek, so their allusions to a representative human city are fraught with cultural meaning. To contextualize and compare their particular evocations of the city metaphor, I incorporate the theories of Edward Said and present cross-references to Eugène Delacroix, the prophecies of Ezekiel, and Shelley‘s poem ‘Ozymandias’. The Holy Land is at once fixed in the exotic Middle East yet necessary for America‘s quotidian social mores. Winthrop and Poe romanticize, appropriate, and exploit Middle Eastern symbolism. The interesting twist, however, is that Poe Orientalizes Winthrop‘s city on a hill, and in so doing, he Orientalizes Winthrop, and perhaps America‘s own religious fanaticism.