Nathan Hale, Class of 1773 (1755–1776). Hale was one of the first Americans captured and executed for spying. He had graduated at 18 with first honors and participated in a commencement debate on “Whether the Education of Daughters be not, without any just reason, more neglected than that of Sons." In 1775, the Connecticut schoolteacher enlisted and quickly rose from lieutenant to captain. In September 1776, Hale was chosen to command a company in Knowlton’s Rangers and volunteered to spy behind enemy lines. Within weeks he was captured by the British and hanged, on September 22, 1776. Captain William Hull, a British officer who attended Hale on the morning of his execution, recalled that the young American “bore himself with gentle dignity." From the scaffold Hale reportedly uttered his famous last words: “I only regret that I have but one life to lose for my country.”

The 1925 stamp bearing his image was the United States' first half-cent stamp. The stamp’s designer based his portrait on the 1914 statue of Hale on the Old Campus (by Bela Lyon Pratt ’99BFA).