Notable Prisoners of the Old Jail
For over six decades, the Old Jail’s imposing walls witnessed the confinement of many different individuals — hardened criminals, vagrants, and those who strayed from the law’s path. Within its cells, infamous figures and local offenders whose stories have been lost to time served their sentences. The Old St. Johns County Jail gained notoriety for its harsh conditions and unforgiving punishments, etching its reputation as one of Florida’s most formidable correctional facilities.
The echoes of these inmates’ experiences still resonate within the jail’s iron-barred cells. Some tales are meticulously documented, while others linger as whispers, blurring the lines between fact and legend. Delve into the Old Jail’s captivating history, where stories of notorious criminals, rumored stays by figures like Al Capone and crimes of passion intertwine to paint a vivid picture of a bygone era.
Henry Flagler
The Visionary Turned Inmate
Henry Flagler is remembered as the man who built modern St. Augustine. As a railroad tycoon and co-founder of Standard Oil, he developed luxury hotels, railways and the city’s infrastructure, turning the once-quiet town into a thriving destination.
Ironically, Flagler was once arrested and held in the very jail he funded. Charged with public intoxication, he spent a brief time behind bars, proving that even one of the most powerful men in Florida wasn’t immune to the law. His stay was short-lived, but it remains a fascinating twist in the Old Jail history.
Sim Jackson
A Crime of Passion
Sim Jackson was a local man whose crime shocked St. Augustine. In a fit of rage, he murdered his wife with a straight razor, a crime so brutal that it stunned even the toughest lawmen.
It took five years before authorities finally arrested him, and when they did, he was brought to the Old St. Johns County Jail. His trial was swift and unforgiving, and he was sentenced to the harshest punishment available at the time.
Charlie Powell
A Jealous Husband’s Revenge
Charlie Powell’s crime was driven by love, rage, and a thirst for revenge. When a local man began spreading false rumors about Powell’s wife, the situation escalated into a deadly confrontation.
Consumed by anger, Powell attacked and beheaded the man, an act that stunned the entire town. He was quickly arrested and sent to the Old Jail, where he spent his final days facing the consequences of his violent retaliation.
His story remains a chilling reminder of how emotions can drive people to commit unthinkable crimes.
Billy the Kid
A Legend or a Lie?
William H. Bonney, better known as Billy the Kid, was one of the most infamous outlaws of the Wild West, known for escaping jails, gunfights and a reputation as a ruthless killer.
Despite his well-documented history, there is no record of him ever being in Florida, let alone locked inside the Old Jail. Still, some say that a man claiming to be Billy the Kid was once held here, fueling speculation that the legend may have stretched beyond the West.
This tale has never been confirmed, but it remains one of the many rumors that make the Old St. Johns County Jail such an intriguing place.
Al Capone
The Gangster’s Rumored Stay
Al Capone was one of the most notorious criminals in American history, ruling Chicago’s criminal empire during Prohibition. His crimes included bootlegging, bribery, racketeering and murder, but he was ultimately brought down by tax evasion charges in 1931.
There are rumors that Capone was briefly held at the Old Jail while being transferred to another prison, but there is no official record of this. What is known is that he served time at Eastern State Penitentiary (1929), Atlanta U.S. Penitentiary (1931) and Alcatraz (1934-1939).
Even without proof, the possibility of Capone’s connection to the jail keeps the story alive, and his name remains tied to its mysterious past.
Female Prisoners at the Old Jail
Though the Old Jail was built for male inmates, women were also sentenced and locked up here. They were kept in separate quarters, but conditions were just as harsh, with little food, cramped spaces and no privacy.
Many were arrested for minor offenses like public drunkenness or vagrancy, while others were convicted of serious crimes. Unlike today, women in the late 1800s and early 1900s often faced jail time for offenses that wouldn’t even warrant an arrest in modern times. Some women found themselves in the Old Jail simply because they ran on hard times and had no family support in the area.
These stories are rarely told, but they are an important part of the Old Jail history, showcasing how justice was carried out differently depending on gender and social status.
