Born in 1907 in New London, Connecticut, Thomas Silvestri Macaione's mother was of Italian and his father of Greek descent. When he was seven years old, the family went overseas to visit family in Sicily and got stranded in the turmoil of World War I. After he returned to the U.S., Tommy began training as a barber in 1925, and supported himself in the trade until World War II. While working as a barber, he developed a serious interest in painting, starting out with portraits and then landscape paintings in oil.
Macaione, medically discharged from the army, studied at the Rhode Island School of Design for two and a half years and then continued on the GI bill at the Art Students League in New York. After his studies, he decided to "go west" and worked for a while in Tucson and then Palm Springs, followed by a stay in San Francisco where he continued to work odd jobs but also drawing charcoal portraits at Fisherman's Wharf.
In 1951, fascinated by an article about Santa Fe, New Mexico, he made his way to the city where he was to become known as "El Diferente" and to stay for the rest of his life. He was well received by the Santa Fe art colony of the day; including Alfred Morang, Randall Davey, Fremont Ellis, Gustave Baumann, and Will Shuster. He later cited Morang and the Fauvist as his major influences.
Employing a thick impasto technique, he quickly became known for his colorful garden scenes and landscapes. A colorful personality, he often traded paintings for animal veterinary care, ran for public office, and most of all became a popular fixture in the streets of Santa Fe, setting up his easel outdoors in all kinds of weather and painting and translating into images the sights and sounds around him.
In 1987, for his 80th birthday, he was given a show and birthday party at the Museum of Fine Arts in Santa Fe, with twenty-five of his canvases on display. As his brother Morris stated in an interview, they went to a restaurant afterward, and Tommy paid for everyone's meal with a painting.
Tommy (Thomas Silvestri) Macaione died in 1992 and is commemorated in Santa Fe by Macaione Park and "El Differente," a life-size bronze dedicated in 1994 at the northeast corner of Marcy and Paseo de Peralta.