The Hamilton Leroy Shields Letter is a handwritten missive from a homesick cadet at the United States Military Academy (also known as West Point) in 1842, to former cadet Philip James Winn, Esquire. The letter discusses Shields's studies, his professional plans, and his desire for a wealthy wife (with at least $50,000). Shields also discusses the day‐to‐day life of cadets—specifically mentioning the frequency of illness, lack of women, student resignations, and the tri‐weekly cotillion parties. Mentioned geographical locations include Lexington and Richmond, Virginia.