The question of diplomatic gifts has become increasingly center stage in studies of Renaissance art. Their importance has not, however, been considered before in relation to the career of Sebastiano del Piombo at Rome. From the very beginning of his time in the city, however, Sebastiano began to paint works of art that were intended as diplomatic gifts. The two major works examined in this light will be the Visitation commissioned, most likely, by the Venetian government for Queen Claude of France and the Pietà commissioned by Ferrante Gonzaga for Francesco de Los Cobos. The argument will show both how central such commissions became to Sebastiano's career and how they may have affected the development of that career.