Cummings, a native of Bath, England, came to New York as an infant and trained with Henry Inman. He was one of the foudners of the National Academy of Design and produced miniatures of noted individuals of his era.
The subject, the son of one of New York's delegates to the Continental Congress in 1778-1779, erected the Episcopal Church of St. Ann's in the south Bronx, New York. A railroad entrepreneur, he was one of the richest New Yorkers of his time.