From NKAA, Notable Kentucky African Americans Database (main entry)
Bailey, John S.(born: 1830 - died: 1892) John S. Bailey, the husband of Julia Frances Bailey, was one of the wealthiest African Americans in Racine, WI. He was born in Kentucky, and moved to Indiana where he married Julia in 1851. By 1857, the couple lived in Racine, where John owned a barber shop. They were two among the 92 African Americans living in Racine, Wisconsin in 1860, and there were several from Kentucky. John's barbering business was a success and he was able to hire others to work for him, including white barbers. Bailey's barber shop was located in the basement of the American Bank in Racine.
John S. Bailey had a home built for his family at 1124 Wisconsin Avenue. His daughter Florence (b.1860) is thought to have been the first Colored student and graduate of Racine High School. Bailey's two sons, George S. (b.1865) and William H. (b.1869), were in the barbering business with their father. His wife's parents were from Kentucky, they had migrated to Indiana where Julia was born in 1833.
A few years after John Bailey's death in 1892, his entire family moved to Fulton, Washington and are listed in the 1900 U.S. Federal Census: Julia was a dressmaker, no occupation was listed for Florence, and George and William were barbers. By 1910, Julia and her sons lived in Seattle, WA. George and William owned a barbershop. Julia Bailey is sometimes listed as Mulatto or white in the census records. By 1920, she is no longer listed, and George and William are still single, they live together, and still own their barbershop. It is not known if their father, John Bailey, was ever a slave in Kentucky.
For more see "History: the John S. Bailey family," Milwaukee Star, 11/28/1970, p.6.