The Knoxville-born Beauford Delaney studied with John Sloan and Thomas Hart Benton at the Art Students League in New York and regularly visited Sloan at his studio in the Hotel Judson on Washington Square South. He showed often at the semi-annual Washington Square Outdoor Art Shows, an experience he found exhilarating. Delaney often sketched in the Square, remarking after a visit in the spring of 1938: "Never before have the leaves and grass been more beautiful—also the old houses around Washington Square seem like large out of shape flowers blooming softly through the trees. I so wish it [was] possible for me to get out into words the deep felt things which are so obvious and tangible…and real like great alive forces working [through] the deep unconscious tracts of our inner consciousness" (Delaney is quoted in David Leeming, Amazing Grace: A Life of Beauford Delaney [New York and Oxford: Oxford University Press, 1998], p. 85).

Delaney created paintings of the Square from the late 1930s through the early 1950s, and his Delaney's later efforts are notable for their lyricism, blending of abstraction and representation, silhouetting of shapes, and free and imaginative use of geometric forms.