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Correspondence, legal papers, and letter books of Shepard. The correspondence, which comprises the largest part of the collection, is rich in information about New York politics and social activities at the turn of the century. The letter books cover the years 1890-1911. The collection also contains legal papers, drafts of speeches, clippings, and memorabilia. Correspondents with Shepard include Felix Adler, Thomas Willing Balch, Frederic Bancroft, Bernard Baruch, Richard Rogers Bowker, William Jennings Bryan, Alfred Clark Chapin, Grover Cleveland, Hamlin Garland, Richard Watson Gilder, Edward Everett Hale, Fletcher Harper, Abram S. Hewitt, Charles Evans Hughes, John La Farge, Henry Cabot Lodge, Josephine Shaw Lowell, Hamilton Mabie, Walter H. Page, Alton B. Parker, George Foster Peabody, Bliss Perry, Joseph Pulitzer, John D. Rockefeller, Jr., Franklin D. Roosevelt, Theodore Roosevelt, Elihu Root, Carl Schurz, Kate Nichols Trask, Oswald Garrison Villard, and Booker T. Washington.

Papers of the Jay family and of those families related to the Jay family, including Bruen, Butterworth, Chapman, Clarkson, Dawson, Du Bois, Field, Iselin, McVickar, Mortimer, O'Kill, Pellew, Pierrepont, Prime, Robinson, Schieffelin, Von Schweinitz, Sedgwick, and Wurts. In addition to family and personal matters, the correspondence deals with anti-slavery, New York State civil service, repeal of the Missouri Compromise, the Civil War, the Blair Bill, international affairs, and New York City and State politics and government. There are letters from numerous prominent persons including George Bancroft, F.A.P. Barnard, Bismarck, William Cullen Bryant, Aaron Burr, James Fenimore Cooper, Ralph Waldo Emerson, Hamilton Fish, Albert Gallatin, Horace Greeley, Nathaniel Hawthorne, Oliver Wendell Holmes, Washington Irving, Frances Anne Kemble, Jenny Lind, Henry W. Longfellow, Seth Low, James Russell Lowell, John Stuart Mill, Alice Duer Miller, Clement Clarke Moore, J.P. Morgan, Thomas Nast, Commodore Matthew Perry, Franklin D. Roosevelt, Theodore Roosevelt, Elihu Root, Carl Schurz, William H. Seward, William T. Sherman, Charles Sumner, and John Greenleaf Whittier.