Billy Bailey was born in January 1947 in Smyrna, Delaware, as the 19th of 23 children. His early life was marked by poverty and abuse. His mother died when he was less than a year old, and his father remarried shortly thereafter. Bailey and his siblings suffered chronic physical abuse from their stepmother. At the age of 10, following his father's death, Bailey and his sister were abandoned by their stepmother at the cemetery. They were later taken in by an older half-brother, who also subjected them to abuse. Social workers noted that Bailey exhibited severe behavioral issues and required professional help. As a young adult, he became known to law enforcement for theft and violent behavior.​

On May 21, 1979, Bailey, facing a potential life sentence under Delaware's habitual offender statute for a check forgery conviction, escaped from the Plummer House, a work-release facility in Wilmington. He sought refuge at his foster sister's home in Cheswold, Delaware. Later that day, he robbed a liquor store at gunpoint. After the robbery, he requested to be dropped off near Lambertson's Corner. There, he entered the farmhouse of Gilbert and Clara Lambertson, aged 80 and 73 respectively. Bailey shot Gilbert twice in the chest with a pistol and once in the head with the Lambertsons' shotgun. He then shot Clara once in the shoulder with the pistol and twice with the shotgun, resulting in their deaths. Bailey arranged their bodies in chairs before fleeing the scene. He was spotted by a Delaware State Police helicopter and attempted to shoot at it before being apprehended.​

In 1980, Bailey was convicted of two counts of first-degree murder, among other charges. The jury recommended the death penalty, citing the heinous nature of the crimes. Although Delaware had adopted lethal injection as its primary method of execution in 1986, Bailey, sentenced prior to this change, had the option to choose his method. He opted for hanging, stating, "I'm not going to let them put me to sleep." On January 25, 1996, Bailey was executed by hanging at the Delaware Correctional Center, becoming the last person in the United States to be executed by this method. The gallows used for his execution were dismantled in 2003.