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The papers consist of correspondence, research files (including notes, transcripts, and photocopies of historical documents), writings, photograph albums, and memorabilia relating to the personal life and professional career of American historian Charles McLean Andrews; his wife, Evangeline Walker Andrews; and other family members. More than half the correspondence is between family members. Charles Andrews's education and early career are detailed in correspondence with his parents, wife, and sisters. Evangeline Andrews's correspondence with her parents; her sister, Ethel Walker Smith; her husband; and her children concerns her Bryn Mawr activities, travels, historical and theatrical interests and writing, and the activities of family members. The correspondence also chronicles the development of the Ethel Walker School. Charles McLean Andrews's professional correspondents include former students, co-authors, fellow historians, librarians, and archivists. The professional correspondence is overwhelmingly incoming and reflects more of the correspondents' careers and activities than those of Andrews. Research and writings files detail Andrews's historical interests.

The papers document three generations of the Woolsey family. The most prominent figures in the collection are William Walton Woolsey (1766-1839), land owner and merchant in New York City; his son, Theodore Dwight Woolsey (1801-1889), Greek scholar, political theorist and president of Yale College; and Theodore Salisbury Woolsey (1852-1929), professor of international law at Yale Law School, son of Theodore Dwight Woolsey. The papers of William Walton Woolsey contain extensive business correspondence, ledgers, legal papers, documents relating to land sales in New York and Ohio, as well as family and personal letters. Since he was engaged in the importation of sugar, cotton and hardware, some of his business correspondence is political with discussions of the Jay Treaty of 1794, the problems of piracy, American neutrality in the 1790s and the general politics of the period. Important correspondents are Chauncey Goodrich, Archibald Gracie, Eli Whitney, Noah Webster, Elihu and Nathaniel Chauncey, Oliver Wolcott, Benjamin Tallmadge, Jedidiah Morse, James Roosevelt, John A. Schuyler, Comfort Sands, John Broome, and Nicholas Bayard. The papers of Theodore Dwight Woolsey contain his writings on Greek language and literature, the Bible, international law and the texts of his sermons.