Gregory is the publisher of the contemporary art magazine Quiet Lunch. He has discovered and written about many artists, from those just emerging to those who have passed on. Gregory studied art at Harvard University, the Museum School of Fine Arts in Boston, and the Universidad Sacrado Corazon in Puerto Rico. As a painter, his consummate skills link him with the Classical Realism revival but his imagery is rooted in surrealism and ancient mythologies. His works are often large, such as the murals he painted for a number of bars, including the Roger Room in Los Angeles. His mythologies are also realized in the surfboards he carves — powerful totemic icons that appear as if they belong to non-literate cultures. He is also the creator of video installations. His works are exhibited in galleries internationally, including the Amstel Gallery in Amsterdam. He continues to curate cultural events and exhibitions through his Bodega de la Haba in New York.