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Most of the collection deals with Willard's ownership of the famous Willard Hotel. Extensive correspondence documents the comings and goings of clients at the hotel, as well as repair and financial matters there. Legal and financial papers are concerned with the hotel, as well as with Willard's other interests as founder of the National Safe Deposit, Savings and Trust, Co., as a member of the D.C. Board of Public Works, and as chairman of the Board of Trustees for the District of Columbia Reform School in the 1870s and 1880s. Willard received appointments signed by the President every three years. Thus, the signatures of Grant, Hayes and Cleveland appear here. A few personal items are included, such as an icy exchange between Henry and his brother Joseph C. Willard. Of interest is a long document to the Supreme Court of the District of Columbia which details the feud between the two brothers.

Contains document files.