Remembered as both a politician and a successful businessman, this conservative "Bourbon" Democrat served as President Grover Cleveland's first Secretary of the Navy and made his fortune in the legal, railway, steel, coal, financial, and horse racing industries.
After graduating from Yale University in the early 1860s, he pursued a law degree at Harvard College.
Over the course of his life, he bred nearly thirty American race-winning horses.
A member of the wealthy and socially prominent Whitney family, he grew up with a brother, Henry Melville Whitney, who headed major steamship and railway companies, and with sisters, Lily and Susan, who married into other prominent families. His marriage to Flora Payne produced children named Harry, Pauline, Payne, Oliver, and Dorothy; his second wife (whom he married after Flora Payne's death) was Edith May.
His oldest son, Harry Whitney, carried on the Whitney family's horse breeding legacy, producing a dozen Kentucky Derby horses.