He was born on December 14, 1872 in Vallejo, California to E.M. Benjamin, who was also an attorney. Benjamin was admitted to the California Bar Association in 1893. He started off his career in law by working for a local law firm in Vallejo.
In 1902, he married Mildred Frances, the daughter of G.M. Francis, the owner and publisher of the newspaper the Napa Register.
Benjamin served as Napa County's district attorney from 1901 until 1907, when he was promoted to the chief deputy to the attorney general of California, Ulysses S. Webb. He resigned in 1919, to return to private practice. He participated in the U.S. Supreme Court trial Pullman Co. v. Richardson, 261 U.S. 330 (1923). Benjamin served significant positions in the Republican National Committee.
- "Raymond Benjamin". The San Francisco Bay Region. 1924. "He is a native son, born at Vallejo, California, December 14, 1872, son of E. M. and Ruth S. (Mahon) Benjamin. His father is of English and his mother of Scotch-Irish descent. His mother was born in Pennsylvania. E. M. Benjamin, a native of New Jersey, came to California in 1851 by way of Cape Horn. ..."
- "Benjamin, 79, Lawyer, Dies In Westport. Former GOP Chairman Of California; Was Elks Exalted Ruler". Associated Press in The Hartford Courant. June 19, 1952. Retrieved 2011-12-24. "Raymond Benjamin, 79, retired lawyer and former Republican chairman of California, died at his home here today. ..."