This series primarily reflects the business activities of George C. Woodruff, though the final subseries includes business papers from Woodruff family members and others. The contents of the first subseries reveal much about Woodruff's law studies and practice, including his law school notebooks and his notes on actual lawsuits. The second subseries concerns Woodruff's investments, primarily in banks and railroads, and includes newspaper clippings and printed circulars which reveal the growth and as well as instability of these companies: a circular from the Kansas Pacific Railway Company, for example, mentions the financial difficulties of the organization and the consequential restructuring of interest payments. The third subseries consists primarily of election party tickets and records of election returns, many with his own name as a candidate. The fourth and fifth series contain miscellaneous business notes by Woodruff and others, and include papers relating to Woodruff's involvement in the Litchfield Mutual Fire Insurance Company; his notarial records; and his son George M. Woodruff's law school notebooks.