The items below document Jefferson’s response to the insolvency of his friend and close family connection, Wilson Cary Nicholas. In May 1818 Jefferson had endorsed two notes totaling $20,000 for money that Nicholas owed to the Second Bank of the United States, thus making Jefferson personally liable for that amount if Nicholas could not pay. Large as it was, this sum was dwarfed by Nicholas’s other debts, many of which were supported by prior liens on his property. Although he initially believed mistaken assurances by Nicholas that his estate would be able to satisfy this obligation without calling on him, Jefferson acted quickly to place his own affairs in order. To end the need to request frequent renewals of short-term notes and avoid the possibility of an immediate demand by the bank that he pay Nicholas’s debt, which would have obliged him to sell a great deal of his own property, Jefferson decided to execute a bond committing Nicholas as principal and himself as security for the debt. Since the bank required a second guarantor, Thomas Jefferson Randolph, Jefferson’s grandson and Nicholas’s son-in-law, agreed to act in that capacity. Anxious to protect Randolph and aware that the bank would want some sort of solid asset to back up the bond, Jefferson decided to place 956 acres in Bedford County, including part of his Poplar Forest estate, in trust for payment of the debt if Nicholas defaulted. Jefferson initially deeded this property in trust to Randolph, but Julius B. Dandridge, cashier of the Richmond branch of the Second Bank of the United States, soon informed him that the directors wanted “a person less concerned” than Randolph to act as trustee. The directors accepted Jefferson’s substitution of Bernard Peyton but added Andrew Stevenson as a second trustee. At the request of the directors, the bond was also revised slightly. New versions of both the bond and the deed were duly executed in November 1819, each backdated to 15 Sept. 1819, a date chosen to coincide with the end of the previous promissory notes by Nicholas and Jefferson for the debt. After Nicholas died in October 1820, the burden of this obligation fell directly on Jefferson, and he made almost no headway in paying it off prior to his own death on 4 July 1826. Ultimately the final security, Thomas Jefferson Randolph, succeeded in settling the debt in his own right and as estate administrator for both Jefferson and Nicholas (TJ to Nicholas, 1 May 1818, 24 Aug. 1819; Nicholas to TJ, 5 Aug. 1819; Joseph Marx to TJ, 27 Sept. 1819; Dandridge to TJ, 4 Oct., 10, 27 Nov. 1819; TJ to Dandridge, 3, 19 Nov. 1819).