D.J. Caulfield became staff photographer and later photography editor (and eventually editor-in-chief) of a twice-weekly newspaper published on the East End of Long Island by the Forbes family of Westhampton Beach, NY. In this same time frame, he served as founding member and president of the Southampton, NY-based Free Lance East End Professional Photographers Association (FLEEPPA). D.J went on to own a multi-media regional news service (ELI News Bureau) supplying editorial and photographic content to several outlets, including the Associated Press and Newsday. He also produced magazine cover art as editor of business magazine in Atlanta.