These papers center on the business dealings of Thomas Winn and his son, John, of Fluvanna County, Virginia, who held land and business obligations in Kentucky. Most of the correspondence dates from the 1820s and concerns efforts by agents hired by the Winns to conduct their business in Kentucky. These agents were Major Archibald Bilbo, John Kimbrough, and George and John Thompson. Bilbo and the others described their lengthy (and sometimes unsuccessful) endeavors to collect debts owed the Winns. Much information on the financial instability in the state, the lack of faith in Kentucky banks and bank notes, and the passage of laws to relieve debtors is included. A particular case involving Willis Wills, a connection of the Winns by marriage, is a frequent subject. Wills refused to pay his obligation and Bilbo reported that the newly passed debt relief laws of the 1820s would probably protect him. Bilbo also stated that Wills was a candidate for the General Assembly and that he believed Wills would sponsor further legislation on behalf of debtors if elected. Some later materials from the 1860s and 1870s are also present. They concern Dr. Philip J. Winn of Winnsville, Virginia and his subscriptions to various medical journals. Dr. Winn apparently was a descendant of Thomas and John Winn.
