Benjamin DeCasseres was born 3 April 1873 in Philadelphia to David DeCasseres and the former Charlotte (Lottie) Davis. DeCasseres—spelled many ways, though Benjamin preferred it without the spaces—was an old Spanish-Portuguese Jewish family with deep roots in America and a collateral connection to the philosopher Baruch Spinoza. David, who had been born in Jamaica, was a bookkeeper; Charlotte had been born in Pennsylvania, to parents from Hungary and Bavaria. Benjamin was the oldest of four children, two sisters and a brother, Irma, Edith, and Walter.
The family faced a good deal of upheaval in the early 1880s. Benjamin was attending the local schools. In 1880, aged only 3, Edith DeCasseres, his youngest sister, died. Two years later, the family had another child—that was Walter. In 1886, when he was 13, Benjamin dropped out of school and went to work for the Philadelphia Press, first as an office boy, but working his way up to proofreader. He stayed in the business until 1899. In early 1900, Walter was apparently trying to follow in Benjamin’s footsteps, and had called at a print shop, but presumably had been turned down, which is when tragedy revisited the family: he went missing February 4th. His body was later found floating in the Delaware River; police assumed he had drowned himself after not being able to find work. He was 18. News reports of the discovery appeared in the newspaper on Benjamin’s 27th birthday.