Livingston “Castro” Roberts (1942−2004) was one of the early Highwaymen, who even as a child had dreamed of becoming an artist. He received his unusual nickname because his friends thought his beard gave a resemblance to Cuba’s Fidel Castro. After moving from Elkton, Florida, to Fort Pierce in 1963, Roberts became close friends with Harold Newton and Alfred Hair. Roberts painted with them, and he generously taught many future Highwaymen how to paint. Along with the other painters, Roberts painted long into the night out of a sense of loyalty to Hair.

Roberts was upset by Hair’s death and, in 1970, moved to Castile, New York, with no plans of returning to Florida. While there, he painted northern scenes that included all of the seasons. Roberts eventually returned to Florida around 1975, and his house soon became a gathering place for painters. He was an amiable and natural teacher, and people gravitated toward him. As many as twenty-five to thirty people gathered in his yard to watch him paint and learn from him. Roberts’s work is noted for its luminous quality. He used layers of paint, blending colors together to capture the radiance of a scene.