James Gillespie, founder of Gillespie’s Hospital, and his brother John rose from modest beginnings near Edinburgh to considerable prosperity through industry and the tobacco trade during the American War. Unmarried and frugal yet generous, James lived simply at Spylaw, treating his servants with kindness, showing indulgence to tenants, and maintaining lifelong habits of work and benevolence. At his death in 1797, he left his estate and a substantial fortune to establish a charitable hospital and school in Edinburgh for the support of the elderly poor, particularly former servants and those bearing his name. Opened in 1802, the institution reflected his humane values and enduring concern for social welfare, and remains a lasting monument to his character and philanthropy.