James Bowdoin III greatly admired Thomas Jefferson’s republican principles and felt a kinship with his interest in art and culture. After Jefferson appointed him Minister Plenipotentiary to the Court of Spain, Bowdoin offered his services to acquire paintings and sculpture for the President while abroad. Indeed, shortly before his departure for Europe in 1805, Bowdoin presented to Jefferson a marble copy of an antique sculpture in the Vatican’s collection that he believed to represent the Egyptian queen Cleopatra (later identified as Ariadne). The gift remains at Jefferson’s home, Monticello. In 1805, Bowdoin commissioned Gilbert Stuart to paint official likenesses of the President and Secretary of State James Madison for display in his new residence in Madrid. Setting aside the outward trappings of monarchy, Stuart created a pair of portraits that emphasize individual dignity and thoughtful intensity as the chief qualifications for leadership.