Henry Michael O’Connor was born in Brookline, Massachusetts in 1891. He studied at the Massachusetts Normal Art School, the Boston Museum of Fine Arts with Joseph DeCamp, Edmund Tarbell, and Abbott Thayer, and, later, in Paris at the Académie Julian. He was also a pupil of Joseph Pennell. O’Conner worked in various mediums and became proficient as an etcher, illustrator, and painter. In 1920, he became an apprentice to Abbott Thayer at his home in Dublin, New Hampshire. He has been described as one of Thayer’s copyists, alongside David Reasoner and Frederick Sisson. Notably, he served as the president of the Salmagundi Club and was a boxer and artist for the Navy. His work is currently in the permanent collections of the Massachusetts State Capital, Harvard University, and the Newark Museum. Much of his work depicts city life in Boston and New York and scenes from his travels throughout Europe. O’Connor is known for his superior draftsmanship.