Reuben Simmons was born in May 1887 in St. John, New Brunswick to Moses Simmons and Jennie Percy. His father died in Canada when he was two. In 1892, Mr. Simmons immigrated to the United States when he was around five. By 1900, he was a prisoner at the House of Reformation in Boston, Massachusetts.
Mr. Simmons was later committed to the Massachusetts State Prison in Charlestown. He died by suicide in his prison cell on April 2, 1907, at 19.