Floyd Allen was born on July 5, 1856, in Carroll County, Virginia, and lived most of his life in Cana, a rural settlement below Fancy Gap Mountain. He was the head of the Allen family, one of the wealthiest and most politically influential clans in the area. With extensive landholdings, a thriving general store, and political connections tied to Southern Democratic power structures, the Allen family exerted enormous local influence. Floyd himself was known as both a generous benefactor and a man of pride and temper, often prone to violence and quick to assert his dominance over adversaries.

While Floyd Allen's public persona was one of a prosperous and upstanding patriarch, his private conduct was far more violent. Throughout his life, he accumulated a long history of physical altercations, feuds, and criminal charges. These included the killing of a Black man in North Carolina for allegedly trespassing while hunting, beating a police officer, and shooting his own cousin during a family dispute. His body bore at least thirteen bullet wounds, five of them received during shootouts with relatives.

Allen’s criminal record dated back to the 1880s, when he was charged with assault, though charges were often dismissed due to local loyalty or fear. He was once fined for shooting a neighbor during a land deal conflict and had a notorious 1904 case where he shot his brother Jack, a local constable, during an argument over their father's estate. Although Allen was convicted and sentenced to an hour in jail, he refused to serve even a minute, declaring, “I will never go to jail as long as the blood flows in my veins.”

Despite—or perhaps because of—his violence, Allen held various law enforcement titles. In 1908, he and a relative were convicted of assaulting prisoners while serving as deputies, yet they received clemency from the Governor just one month later, which restored their rights to hold public office. His brother Sidna Allen also had run-ins with the law, including a federal counterfeiting trial and perjury conviction in North Carolina. These criminal histories did little to shake the Allens’ control over regional politics until the early 20th century reforms weakened local judicial autonomy.

The eventual transition from county courts to circuit courts in Virginia eroded the family’s power base, as judges became less susceptible to local influence. This judicial shift, combined with rising political tensions and personal grudges, set the stage for the violent climax that would seal Floyd Allen’s fate.

In December 1910, a fight broke out in Hillsville between Wesley Edwards and Will Thomas over a girl. Wesley's brother Sidna joined him, and both were charged with several offenses. To avoid arrest, they fled to North Carolina, but were eventually apprehended by law enforcement and transported back to Carroll County. While being taken to court, Floyd Allen intervened. He attempted to help his nephews escape and ended up fighting with Deputy Sheriff Thomas Samuels. During the struggle, Floyd injured Samuels, and the Edwards brothers were released.

Floyd was later indicted for assault and other charges. He testified before a grand jury, acknowledging that he had roughed up Samuels but denied any intention to free the brothers completely. Amid political tensions following an election, the prosecution sought to hold Floyd accountable. As tensions rose around the trial, rumors circulated that Floyd had threatened a deputy, prompting many officials to arm themselves in fear of retaliation from the Allen family.

On March 13, 1912, Floyd stood trial. During the proceedings, the jury was unable to reach an immediate verdict, and they were held overnight for deliberation. When the jury returned a guilty verdict, Floyd threatened Judge Thornton Massie. In response, the judge sentenced him to one year in prison. Following the sentencing, chaos erupted in the courtroom. Accounts vary regarding who fired first, but a shootout ensued between the Allens and court officials, resulting in multiple fatalities and injuries.

Judge Massie, Commonwealth's Attorney William Foster, Sheriff Webb, and two jurors were killed in the crossfire. Additionally, several others were injured, including Floyd himself, who was shot and unable to flee the scene. After the shooting, Floyd was found hiding in a hotel. He attempted to take his own life but was stopped by the sheriff's deputies.

The aftermath of the courtroom shooting led to a massive manhunt for Floyd and other members of his family. Many were captured, but others fled. The state of Virginia called in detectives to help find those involved in the violence.

Eventually, Floyd Allen was tried for the murders of the officials killed in the courthouse shooting. The trial proceedings revealed evidence of potential conspiracy and weapons purchases leading up to the courtroom chaos. Floyd and his close relatives were found guilty, receiving different sentences, with Floyd and his son Claude receiving death sentences by electrocution.

Floyd Allen was executed on March 28, 1913. His family members also faced convictions for their roles in the incident, resulting in a range of prison sentences. The events of that day left a lasting impact on Carroll County, leading to changes in law enforcement and the judicial system in the region.