Robert Charles Winthrop was born in New York City on May 2, 1874 to John Winthrop and Louisa (Cady) Winthrop. He was educated under private tutors at various boarding schools including Groton School, Norwich Academy, and Harvard College. He married Harriet Hatch Winthrop of Boston on November 25, 1901. They had four children: Robert Winthrop Jr
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(1902-1931), Richard Winthrop (1905-1940), William Hatch Winthrop (1908-1980), and Harriet Elizabeth Winthrop (1911-2000). He was a member of the New York State Bar Association from 1908 to 1940.