John W. Headley was born February 13, 1841, at Providence in Hopkins County, Kentucky. He worked in his father’s store in Madisonville at the age of twelve. By the age of seventeen he had become an expert accountant. He joined the Confederate army at the age of twenty. He served as a spy for General Braxton Bragg and rode with General John Hunt Morgan. Later in the war, he served with the Confederate Secret Service under Colonel Robert Martin in Canada. In 1906 Headley wrote a book dealing with his wartime service for the Confederacy entitled "Confederate Operations in Canada and New York".
He married in Tennessee after the war and then engaged in the tobacco business in Evansville, Indiana. From Indiana he moved to Louisville as a member of the tobacco house of Givens, Headley & Company. In his book he recalls that after the war he spent two years in Hopkins County, sixteen years in Evansville, Indiana, and twenty years in Louisville.
Headley was a lifelong Democrat who served as Secretary of State from 1891 to 1895 in the administration of John Young Brown. He is listed in the federal census of 1900 and 1910 as living in Louisville with his wife Mary J. and children.
Sometime after 1910, he moved to Beverly Hills, California, where he died on November 6, 1930. He is buried in the Inglewood Park Cemetery in Inglewood, California. He was survived by four sons (Percy, John Jr., James, and Wallace) and two daughters (Ann and Mary). Percy and John were living in Los Angeles, California, in 1930.
"Political Graveyard Website";
Samuel Elliott Carpenter, ed.,"Illustrated Centennial Record of the State of Kentucky, 1792-1892," (1892), pgs. 30-31;
"Interment Records," Inglewood Park Cemetery;
John W. Headley, "Confederate Operations in Canada and New York," (1906), pg 461;
Federal Census of 1900 and 1910;
Obituary, "Louisville Courier-Journal," November 13, 1930.