In 1881, Dr. Caleb Headley died of a lingering Civil War wound, leaving his young widow, Sarah, in a tough predicament. As the 32-year-old mother of six children — ranging in age from fifteen to two — she assumed charge of the family estate (a $100 house and 455 total acres), all of which was situated on a creek where she had no in-laws or immediate family to assist her. She chose not to remarry but did commence some sort of an affair with a Porter, which resulted in the birth of a son named Moses C. Headley on December 20, 1884.

The initial task of keeping the family afloat financially fell on Caleb’s oldest son, Johnny Headley. “After Caleb died, Uncle Johnny had to keep Grandma Sarah, and his brothers and sisters,” said Ward Adkins, an 81-year-old step-great-grandson to Doctor Headley, in a 2003 interview. “He ran rafts and made whisky and he farmed to make money. Everybody made whisky. It wasn’t a big thing.” In the mid-1880s, Johnny Headley married Emaline Susan Sias, a daughter of Henry C. and Sarah (Plumley) Sias, and settled on nearby Steer Fork.

Sarah, meanwhile, deeded off large parts of her property to provide for her remaining children. In 1884, she sold 174 acres of the family property to William A. “Billy” Sias, a neighbor and son of the local postmaster. Two years later, she sold 160 acres adjoining the homeplace to John Neace.

Around that time, her oldest daughter, Ida Cosby Headley, married John Henan Fry, a son of Christian T. and Elizabeth (Hunter) Fry of Green Shoal. They settled near Sarah on Sulphur. “Old man John Henan Fry was a quiet, docile kind of fellow and easy-going,” said Adkins. “Aunt Cos was awful good to kids, but now some of her boys were pretty rough and kind of sneaky. They’d pilfer a few things along the way from neighbors. They said they had a big cave up in that hollow and it was plumb full of chicken feathers and bones and geese feathers where they’d steal them chickens and things and take them up there and eat them. They just done as they pleased.” John Henan and Cosby Fry remained nearby until 1923, when they moved to Daisy in Logan County. (In 1925, Everett and Annie Sias bought their property.)

In the late 1880s, based on tax records, Sarah Headley’s financial woes continued. The valuation of her home, estimated at $100 from 1882 until 1887, dropped to $50 by 1890, before finally leaving the record books altogether by 1891. In that same time frame, the Headley home was destroyed by fire.

“Will said when he was eleven or twelve years old, the house burned and the family almost starved to death,” said Adkins. “He said the corn crib was close enough to the house when it burned that the fire parched all the corn. Well, they ground that corn up in an old coffee grounder, I guess. Then they’d ‘thrash’ birds at night using pine knots for light. One would kick the brush pile and scare the birds out and the other one would take the brush and knock them down. And Will said they’d clean them birds and cook them in with that parched corn they ground up and make a gruel. They ate that all winter. They had it tough. Grandma Sarah dug may apples and sold them for three cents per hundred pound.”

In this time of extreme hardness, Will Headley, Sarah’s third oldest son, went to live with her brother, Burl Farley, a wealthy timber man on Big Harts Creek in Logan County.

“When Will was about twelve year old, he went up on Harts Creek somewhere to stay with his uncle Burl Farley,” said Adkins. “Uncle Burl was pretty well to do. He worked for Cole and Crane Timber Company up on Pigeon Creek — the Brown’s Fork of Pigeon, I believe Will said. Will worked up there with him. Uncle Burl ran the timber part of it and Granddad took care of the stables and ran errands.”

“Will used to pushboat for a company on the Guyan River,” Adkins continued. “They took stuff out like ginseng. He told me it was so cold one winter — you might have heard them talk about that cold Friday or cold Saturday — his ears froze and busted. He said they bought chickens where they tied up for the night and they would dip them down in the water and pull them back out and all them feathers would just pull right out. He called it ‘scalding them’ but it wasn’t. It was just so cold it shrunk their skin up and the feathers come out easy.”