Jay became involved in exhibiting his paintings after friends entered his work in the Monterey Jazz Festival art competition (without telling him) which he won.Other art exhibits followed both locally and in San Francisco sometimes showing in the same galleries with his neighbor Joan Savo. Artists had fewer venues to exhibit and sell their work as the number of art galleries at that time were few compared with the present day art industry. In 1952 Jay and Joan created a gallery named "Threadbare Square" at 485 Ocean View Avenue in Pacific Grove California across the street from the current Lovers Point Grill.The gallery was in a victorian home they rented in which they exhibited their work.It also included a sand box where visitors could draw in the sand with sticks.
Jay Chaffin judging art competition at Monterey Peninsula Fairgrounds- 1954. John La Piere (to his right) later became the art instructor at Monterey Peninsula College
Being a prolific figurative draftsman Jay produced a large body of drawings in sumi ink, charcoal and graphite pencil . These drawings became studies for his evolution into figurative painting in the San Francisco Bay Area Figurative Movement style which was prevalent in Northern California during the 1940's and 50's. Jay's work evoked a strong visual sense of expressive brush work and mid to dark color tones which gave his work an energy and sense of purpose.