Oliver was born in Boston, Massachusetts, on September 13, 1847. He was a son of Daniel Augustus Oliver and Elizabeth Willard (née Shaw) Oliver (1823–1850), who died three years after his birth.
His maternal grandparents were Robert Gould Shaw and Eliza Willard (née Parkman) Shaw. Through his abolitionist uncle Francis George Shaw and, his wife, Sarah Blake Sturgis Shaw, he was a first cousin of Josephine Shaw Lowell (wife of Charles Russell Lowell) and Robert Gould Shaw (who was killed at the Second Battle of Fort Wagner during the Civil War). Through his uncle Quincy Adams Shaw and, his wife, Pauline Agassiz Shaw, he was also a first cousin of wealthy landowner Robert Gould Shaw II (who was the first husband of Nancy Langhorne, who later became Viscountess Astor).
He graduated from a military academy in Ossining, New York.

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