Dorothy Sherwood was born in St. Louis, Missouri, as the third child of Thomas Caskey, a foundry worker. Her early life was marked by hardship; her mother died when Dorothy was nine, leading to her placement in an orphanage. In 1925, she joined the Salvation Army, traveling through southern cities and singing gospel hymns. Later, she transitioned to burlesque dancing, performing in the chorus line in Chicago. She married James Sherwood, a stagehand, during a performance as a publicity stunt. The couple moved to Newburgh, New York, where they faced financial difficulties. James suffered from tuberculosis and died in a sanitarium, leaving Dorothy to care for their two children. After losing her job and facing eviction, Dorothy's circumstances became increasingly dire.

On August 20, 1935, in a state of despair, Dorothy Sherwood drowned her two-year-old son, Jimmy, in Moodna Creek, Newburgh, New York. She then carried his body to the police station, expressing that it was too difficult to provide for them both. Her case was notable as the only first-degree murder case involving a woman in Orange County at the time. In January 1936, she was convicted of first-degree murder and sentenced to death. However, public outcry and petitions led to a review by the New York Court of Appeals, which overturned the conviction. In September 1936, Dorothy pleaded guilty to first-degree manslaughter and received a six-to-fifteen-year sentence. She was paroled on December 27, 1939, after serving three years and three months. Post-release, she worked in clerical roles for the Salvation Army and was permitted to visit her daughter.