Stuart was invited to Dublin in 1787 for a commission and seized the opportunity to escape the competition of London and his mounting debts there. Painting in the English manner of his London portraits, he quickly established himself as the most successful portraitist in Dublin; however, he took on so many commissions that he failed to finish a number of them, even after taking partial payments at the first sitting. After purchasing a farm outside the city, Stuart went into debt and landed in jail briefly in 1789. Despite this setback, his successes were numerous and included the ambitious portrait of John FitzGibbon, the newly appointed lord chancellor. Splendidly clothed in the robes of his new office, the chancellor peers out beneath a long, full wig, his haughty countenance a perfect expression of his imperious attitude. Painting this type of regal full-length portrait, meant for public display, would serve Stuart well when he returned to the United States to paint its new president.
George Washington’s defeat of the British army in the American Revolution and his inauguration as America’s first president in 1789 had made him a legendary figure in America and abroad. Stuart hatched a plan to return to America to paint Washington’s portrait and "make a fortune by Washington alone . . . if I should be fortunate I will repay my Irish and English creditors." He set sail in March 1793, leaving numerous unfinished canvases behind, remarking, "The artists of Dublin will get employed in finishing them."