Isabella and her husband, John “Jack” Gardner, met the artist Antonio Mancini in Rome in April 1895 through their mutual acquaintance Ralph Curtis. They bought the pastel, "The Little Groom" (found in the Blue Room on the first floor) and arranged for the painter to join them in Venice to paint Jack’s portrait. It was the year of the first Biennial International Exhibition in Venice. Mancini sent two pictures to it, and the portrait proposal enabled him to be at the opening of the Exhibition. The portrait was painted at the Palazzo Barbaro, where Isabella and Jack were staying with their friends, expatriates Daniel and Ariana Curtis. In Venice on April 21, 1895, Jack Gardner recorded in his diary: “[Ettore] Tito and Mancini lunched with us. Afterwards Mancini made a crayon sketch of me and decided how to paint the portrait in oils.”  He worked almost daily on the portrait until the Gardners left Venice in mid-May.  

Mancini’s paintings have only a minimal suggestion of spatial depth, an effect heightened by his heavily impastoed surfaces. In the 1890s, the artist usually divided his canvases into a system of squares, a “graticola” like the traditional system of transferring a design to a larger size. Mancini felt the mathematical process allowed him to capture the passions and sentiments of his subjects.  The remnants of his graticola can be seen in the background of this portrait.