James Alexander Headley was born on March 16, 1831 in Fayette County, Kentucky to parents James S. Headley and Malinda Atchison Headley. His was named in honor of his father and his great-grandfather Alexander Atchison. He was the third of four sons in his family. James attended local schools before going to Transylvania to get a law degree. He graduated valedictorian of his class, meaning that he was able to give a speech during the graduation ceremony, which he did, delivering the speech completely in Greek. Rather than going straight into a profession in the law, James got work as a tutor in the Jessamine County home of Edward Carter. There James met Fanny Carter, the eldest child in the family and the only daughter; it is unclear whether or not James was Fanny's tutor, as she had at one point been sent to Lexington to a finishing school where she boarded. She was just a year younger than James, and in 1852, they were married. 

Shortly after their marriage, James and Fanny moved to Atchison, Kansas. The town was named in honor of David Rice Atchison, town founder, Missouri senator, and first cousin to Jame's mother Malinda. Atchison, an ardent Southern sympathizer encouraged settlers, especially those from the South, to come to the town named for him. This included many of his family members like James and Fanny. While in Kansas, James served a lawyer and a judge in the growing town. Things seemed to be going fine until 1861 when tensions between Southern and Northern supporting settlers in Kansas came to a head. Southerners like James and his family became unwelcome in the town, and eventually they fled Atchison entirely, leaving many of their possessions behind. James, Fanny, and their two young sons Edward and Joseph went first to Missouri to stay with family before returning to Lexington in the midst of the Civil War. 

Once in Lexington, the family first stayed with Fanny's mother Elizabeth Stanhope Carter before James S. Headley bought them a farm of their own on Russell Lane. For many years they lived on this farm in a modest house, one that James would later describe as a shack. It wasn't until the late 1870s that the family moved into Lexington. James began his 18 years of service as the Clerk of the Circuit Court, and living in Lexington made more sense. Fanny purchased a lot of land on West 3rd Street, and they built a large home. They began attending First Presbyterian Church, transferring from Mt. Horeb where they had attended while living in the county. James lived until the age of 81, passing away in Lexington in 1912. He is buried in the Lexington Cemetery.

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