Born in Rome, NY, James Milton ("Jim") Sessions spent much of his life in and around Chicago, IL. He trained at the Art Institute of Chicago from 1903-1906, and initially supported himself as a wheelsman aboard Great Lakes ships from 1906-1914, and later as a commercial illustrator. From 1933, he began to focus exclusively on watercolors and traveled widely as a reporter in WW II, and on numerous trips to Rockport, MA, Nova Scotia, the Southwest and the Caribbean. Although very prolific in the style of John Whorf and Ogden Pleissner, he destroyed much of his work. The current offering, executed around 1958 in Jamaica, represents a colorful surviving example of his Caribbean work.
Detail and signature LR: