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Rose "Libby" Cleveland was “a woman of unusual gifts, of large and varied information, of vigorous views and strong convictions.” Born in New York in 1846, she was the youngest of Richard and Ann Cleveland’s nine children and the sister of future President Grover Cleveland, who was nine years her senior. Miss Cleveland attended school at Houghton Seminary, taught in Pennsylvania and New York, and exhibited a particular passion for literature.

When her unmarried older brother became president in 1885, Miss Cleveland moved to Washington, D.C. to serve as White House hostess. As first lady, she hosted traditional receptions and dinners at the White House while also pursuing her own academic interests. For example, although Miss Cleveland was only first lady for fifteen months, she found time to author two books: George Eliot's Poetry and Other Studies (1885) and The Long Run (1886). Despite Rose Cleveland’s preference for intellectual pursuits over social gatherings, her receptions were well-attended and she was well-liked. On June 2, 1886, President Grover Cleveland married Frances Folsom in the Blue Room, and his new bride took over as first lady.

After leaving the White House, Rose Cleveland spent her years teaching and writing, and remained a frequent visitor at the Executive Mansion. She published a third book, The Soliloquies of St. Augustine in 1910, and during the final years of her life, she had a romantic relationship with Evangeline Marrs Whipple, an activist and philanthropist. A number of their love letters are in the archives of the Minnesota Historical Society. The two women moved to Bagni di Lucca, Italy together in 1912, where they lived until Rose Cleveland passed away from the Spanish Flu on November 22, 1918. They are buried next to each other in the Bagni di Lucca English Cemetery.