"Paradox of Elitism: Vision, Risk, and Diplomacy in the European Career of Colonel John Trumbull (1756-1843)" reconsiders Trumbull's life and works within the context of the eighteenth-century Federalist political ethos, American foreign policy, and nationalist trends of the Neoclassical academic style through the War of 1812. Articulating Trumbull as a Smithian "economic man" through five chapters, this study explores his artistic practice as the foundation and formulation, but also the failure, of a conservative Federalist aesthetic that was usurped when a more radical Democratic-Republicanism became the dominant cultural discourse in the first decades of the nineteenth century. Deeply faithful to Alexander Hamilton, Trumbull saw himself fulfilling the proper role of the public American artist, embracing the so-called 'invisible hand' of the market to facilitate his vision.

Trumbull, like the Federalists, faded into unpopularity in the first decades of the nineteenth century, but given his prominence in the Federalist community, he, much more than the decidedly neutral Gilbert Stuart, ought to be credited as the inventor of Federalist vision---the politically-infused synthetic Neoclassicism that expressed the fair rule of the executive few over the following many. The dissertation's first two chapters reassess Trumbull's early life through his service in the Continental Army, and to his mysterious first trip to Europe, on which he took part in a secret plot with Benjamin Franklin, entered artistic study in London with Benjamin West, was arrested on suspicion of espionage, imprisoned, and eventually granted freedom.

The third and fourth chapters follow Trumbull through the most imaginative and productive phase of his career, between 1784 and 1789, and explore the ways in which Trumbull merged the nationalizing styles of academic Neoclassicism in Great Britain and France, with continually evolving academic theories of art and his own rational, commercial view of the world that reduced the idea of history to variables of risk and profit. The product was Trumbull's own synthetic modes of historical painting and portraiture. The final chapter of this work examines the ways in which Trumbull, in his dual roles as an American diplomat and a picture-dealer in Europe in the 1790s, attempted to integrate risk management, United States foreign policy, and connoisseurship into his Federalist political enterprise.