Oliver Wolcott, Jr. (1760-1833), secretary of the treasury and governor of Connecticut, was patron and subject of numerous portraits during his lifetime. The artists who made them, John Trumbull, Gilbert Stuart, Thomas Sully, John Vanderlyn, and Rembrandt Peale, were among the most noted of the early republic. Wolcott's portraits have not been studied as a group. Retained by individual family members or donated after his death to public institutions, they have remained uncatalogued, even misattributed. Examination of portraits of Wolcott, those he commissioned of others, and his comments about them in his papers reveal greater understanding of the geometric rise in the number of portraits commissioned in the late-eighteenth and early-nineteenth centuries in a the United States. Such a study also reveals important examples of political portrait commissions among the Federalists.