Winfield S. Divine was born on November 9, 1852, in Fallsburg, New York, to Bradley Divine and Ann Mason. His father was a farmer who owned $2,000 of real estate by 1850. He grew up and attended school in Fallsburg, and his father "deserted" the family in the late 1850s. By 1860, he was living in his grandmother’s household in Fallsburg. He moved to Illinois in the 1870s, and he married Mary E. Graham around 1877. They had two children: Fred, born around 1878; and Floyd, born around 1883. They lived in Sycamore, Illinois, and he worked as a carpenter. They moved to Chicago, Illinois, in the late 1800s. His wife died in 1932, and he passed away in Chicago on March 19, 1942.