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Elizabeth Caldwell (born Elizabeth Gordon) married Andrew Caldwell of Dublin (1733-1808) who is believed to have been one of Gilbert Stuart's best friends and confidants. Andrew Caldwell's portrait painted by Stuart, from the Caldwell Family, was sold by Sotheby's in London in 1969.

Andrew Caldwell was admitted to the bar in Dublin in 1760, but not needing to earn a living, devoted himself to literary and artistic pursuits. He wrote Observations on the Public Buildings of Dublin, which he published anonymously in 1770. In 1804 he privately printed and circulated Account of the extraordinary Escape of James Stewart, Esquire (commonly called Athenian Stewart), from being put to death by some Turks in whose company he happened to be travelling.

Gilbert Stuart studied painting with Cosmo Alexander in Newport, Rhode Island before leaving for London in 1775. There he joined Benjamin West's studio from 1777-1782 where his portrait style evolved. He had a successful practice in London from 1782-1787 until he fled to Ireland to escape his creditors, the result of living too extravagantly.

Upon arrival in Dublin he quickly asserted himself as the finest portrait painter outside London. In Ireland Stuart counted among his sitters most of the elite members of society, but he remained always deeply in debt. In 1790 he was briefly incarcerated in debtor's prison. He remained in Ireland until 1792-1793 when debts again forced him to leave for America.

Upon returning home Stuart rose to become the most prominent portraitist in America during the Federal period. Five presidents as well as many other politicians and distinguished figures sat for the artist. Today he is revered as a national treasure. His paintings hang in numerous American and European museums. His portrait of George Washington on the dollar bill is emblematic of America. In a letter dated Dublin, June 12, 2001 Dr. Michael Wynne wrote, Attribution sustained by Michael Wynne having examined a color transparency and a black and white photograph.