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This article sets the American career of Mathew Carey against his political and publishing involvements in Ireland. Arriving as Carey did in America at the age of twenty-four, these involvements were short-lived, but their influence was long lasting. His largely overlooked pamphlet, The Urgent Necessity, published in Ireland in 1781, clearly revealed his despair that “oligarchy” could promote reform and that, paradoxically, it could nurture only resentments and prejudices. For him, the breaking of oligarchy was the only way in which a harmonious and self-confident polity could be cultivated. The attempts of the Irish administration to muzzle his newspapers also encouraged a commitment to champion the freedom of the press in America not only as a just cause but as a way of venting differing opinions and, thus, create a more inclusive polity. Carey was ever the champion of accommodation in his adopted city of Philadelphia, and this article suggests an explanation by reference to his Irish experiences and how they predisposed him to support Jeffersonian Republicanism.