During the late eighteenth century, Ralph Earl (1751-1801) was one of New England's most successful and prolific artists. His success was largely due to his ability to adapt his style to suit the lifestyles and preferences of his sitters. A Loyalist during the Revolutionary War, Earl lived in England from 1778-1785. There, he associated with other artists such as his compatriots, John Singleton Copley and Benjamin West, and England's reigning painter, Sir Joshua Reynolds. He quickly learned the more painterly, abstract style favored in England. Upon his return to America, Earl soon made his way to New York where, after failing to pay a debt, he was thrown into debtor's prison in City Hall. With the help of the Society for the Relief of Distressed Debtors, Earl was able to earn his way out of prison by painting likenesses of the charity's members as well as their friends and family. For these portraits, Earl employed the fashionable style he had learned in England, which suited the urban sophistication of his New York sitters many of whom had been Loyalists during the War. One of the most successful of these portraits is that of Mrs. Alexander Hamilton now in the collection of the Museum of the City of New York. As they were painted in prison, Earl relied on generalized landscapes or interior settings for backgrounds and stock props for furniture and costumes see Elizabeth Mankin Kornhauser, Ralph Earl: The Face of the Young Republic (New Haven, 1991), pp.33-38, for the portrait of Mrs. Hamilton, see cat. 22).
Dated 1787, this portrait of Jacob Isaacs (d.1831) contains the hallmarks of Earl's New York portraits. Instead of the more linear style that Earl used for provincial New England subjects, Earl depicted Isaacs in the English manner with three-dimensional modeling and freer brushwork. The background is deliberately vague and the green-painted windsor chair probably a stock prop or painted from the artist's memory. The son of a prominent Jewish merchant, Isaacs was the first President of the New York Board of Brokers, which later became the New York Stock Exchange. Isaacs' connection to the Society for the Relief of Distressed Debtors is not known, but Earl had painted his niece and nephew, by marriage, ten years earlier (see Kornhauser, p.296).