Very few letters written by James Fenimore Cooper survive from the period prior to the start of his literary career in 1820. The present article provides the annotated texts of six newly discovered letters dating from between 1817 and 1820, all of which concern the financial crisis that then was confronting the estate of Cooper's father. Five of the letters were addressed by James Cooper to a young lawyer, Thomas Bridgen, who created that crisis by his efforts to recover debts the Coopers owed his own family. Because Bridgen and young Cooper apparently had been acquainted as schoolboys early in the 1800s, their later dealings over financial matters were strongly colored by personal feelings. Bridgen's eventual betrayal of Cooper gave the story a peculiarly poignant tone that is audible, I argue, in several loosely autobiographical novels that Cooper published in the 1840s.