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This collection contains correspondence concerning Chamberlain's work on several Washington and Lee University committees from 1904-1908, including committee work on a chapter house for Phi Kappa Psi and on the new Carnegie library. It also includes his two notebooks from law courses (1875-1876) taught by John Randolph Tucker. Lastly, there is an 1874 photograph of Chamberlain and two fraternity brothers, G. M. Effinger, Class of 1874, and Floyd Farrar, Class of 1875.

This ledger contains an alphabetical list of names of Washington Academy law students who were to receive scholarships between 1908 and 1910. This list also notes the amount due and the due date. There is also a list of the class of 1909.

This collection consists of a former Washington and Lee Unversity law student's class notes. The identity of the student is unknown.

Family papers include Winborne Jr.'s school papers and notebooks from his years at Washington and Lee University, as well as information about his fraternity, Delta Tau Delta. Three folders contain printed matter about his father, Roger M. Winborne, a Class of 1911 graduate of Washington and Lee University Law School.