In the late nineteenth century, as Jackson rebuilt and expanded in the years after the Civil War, one of the city’s most successful real estate developers was an Irish immigrant widow who had already endured extraordinary loss. Matilda O’Leary’s life story is one of resilience, entrepreneurship, and civic contribution. By the time of her death in 1911, she had become one of Jackson’s most prominent property owners, and her obituary described her as “a woman of exceptional business sagacity.”