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.