In the 1870s, Chase and Whittredge led rival factions of American artists. From 1874 to 1877, Whittredge was president of the National Academy of Design, a professional organization founded in 1826 to promote American art. Chase and his friends, who were a generation younger than Whittredge, felt that the National Academy stifled the innovative, European-derived styles they favored and started a competing group, the Society of American Artists, in 1877.

When Chase painted this grand and dignified portrait of Whittredge at work, both artist and model were elder statesmen of American art. Chase inscribed the likeness “To my friend Whittredge” at the upper right, and the esteem in which he held the older man may be surmised by the size of the canvas and the price he would have charged a patron for a similarly sized portrait—$3,000, a large sum in 1890.