Lee Winn’s father was Rev. John Henry Winn, Sr., who blazed the trail and later led the 14 Families from Hogeye in Bastrop County, Texas, to what is now known as St. John Colony, Texas. His wife was Jane Allen, who was born in Alabama. Jane is probably the sister of Rev. Calvin Allen, Sr.
Rev. John Winn, Sr., and Jane Allen-Winn married circa 1862. According to the 1910 census, Jane said she had fifteen children, and nine were still living: Martha, Abraham, John, Thomas, Emma, Spurgeon, Anthony, Lee, and George. The names of the other five children are unknown.
It is believed that Lee Winn, Sr. was a slave, but at this time, the slave owner and location of the plantation are not known.
Lee Winn, Sr. was thirteen years old in 1872 and with his father when the 14 Families left Hogeye for St. John Colony. He was born into slavery in 1859 in Travis County, Texas. Circa 1879, Lee married Emily Walker in St. John Colony. They had eleven children: Ludia, Lee Jr, Georgia, Melissa, Adaline, Jennie, Emma, Atress, Beatrice, Johnnie, Sr., and John.
Lee, Sr. died in April 3, 1948 in St. John Colony. Emily Walker-Winn was born in 1862 and she died September 12, 1922 in Lytton Springs, Caldwell, Texas.