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Letters written to Gay from political and literary contemporaries such as Horace Greeley, Charles Sumner, and William Bryant; reports in letter form from his reporters at the front during the Civil War; and personal correspondence including many letters from his wife, Elizabeth Neall Gay. Letters written to Mrs. Gay from family friends and business associates including many from her husband. Correspondence of other members of the Gay family including Walter Gay, Sarah Gay, and Allan Gay. Diaries, notebooks, and journals of Sydney Howard Gay.

Letters to and copies of letters, letter books, and miscellaneous papers of (George) Frederick William Holls. There is also an amount of clippings and other miscellanea. The correspondence is with many persons important in the areas of politics and education. The subject content of the letters is international in scope, including such matters as the Suez Canal, the Webster-Ashburton Treaty, the Dreyfus affair, the Hague Peace Conference, Rhodes Scholarships, unification of education in New York State, the St. Louis Exposition, and tenement reform. Among the principal correspondents represented by groups of letters are John Barrett, Nicholas Murray Butler, Henry W. Diederick, Theodor Lange, Hugo Munsterburg, F.J. Odendahl, Theodore Roosevelt, and Carl Schurz.

Correspondence, manuscripts of poems, and manuscripts of lectures by Benjamin. The correspondence consists of original letters of Benjamin, typescript and photostatic copies of Benjamin letters in other libraries, and letters to Benjamin from some of his literary contemporaries including Paul Hamilton Hayne, Willis Gaylord Clark, John Lothrop Motley, and Fitz-Greene Halleck. Many of the letters relate to Park Benjamin's lecture tours. There are other family letters and many documents relating to the Benjamin family,and two letterbooks of John Lothrop Motley. Also, a large amount of genealogical material of the Benjamin family, and its related families from the 16th century to the present day. There are also financial records, monographs, clippings, and photographs.