Hauntings of The Old Monroe County Jail

Posted: 09.03.2024 | Updated: 05.27.2025

In its earliest days, Key West wasn’t the tropical getaway it’s known as today, and many heinous characters attempted to shape its future. A part of Jim Crow’s South, it was beholden to the same prejudices exhibited in far less tropical climates throughout the southern states. The energy circulating the Old Monroe County Jail stems from a horrid Christmas, a product of racism and the spread of white supremacy. 

The floors of the old jail in Key West are stained red by man’s villainy. But after the blood faded, the residuals of the brutality didn’t. Even today, whispers of that ill-fated encounter and other tragedies that unfolded within the walls of the haunted jail lend to its ghostly activity. 

Look beyond the tropical beauty of Key West for a darker side that you can explore when you book your Key West ghost tour today.

Who Haunts the Old Monroe County Jail?

Two prominent spirits, both manifested by tragedy, are bound to the old 19th-century jail. Their souls remain in unrest, tormented by the suffering they endured in life. One is a victim of grief, and the other a casualty of antiquated ideals. 

Neither knows peace as they remain anchored to the very jail that ultimately contributed to the extinguishing of their flame. Their despair echoes in every hollow footstep or phantom noise that rings throughout the historic jail. 

Quick Facts:

• The 1892 Old Monroe County Jail is the fifth design of the Key West jail
• Only a small portion of the old jail remains standing today
• A fire that devastated Key West inspired the jail’s sturdy construction
• The infamous haunted Robert the Doll is only 15 minutes away

Early Law Enforcement in Key West

Completed in 1892, the Old Monroe County Jail, which spectral enthusiasts are drawn to, wasn’t the first of Key West County’s jails. By then, it had been built and rebuilt three other times. The original prison was converted from a ship’s brig near the island’s edge in 1828. 

In its earliest form, the Key West jail was used less to detain and more as an administrative building. Though there was a marshal who oversaw local law, crime was relatively uncommon. With a population of less than 500, the opportunity was rare. 

In fact, within the first 50 years, Key West had only three felony convictions. That started to change as the population grew, and the need for a more functional facility became evident. By 1835, the jail underwent its first reconstruction, making it a suitable space for more prisoners.

The Fifth Iteration of the Monroe Jail

The timeline for the Monroe County Jail gets muddied the more you dig into its past. Some sources confuse the 1828 facility with the 1892 building. Then there are the many versions, with the historical marker at the current Old Monroe County Jail citing rebuilds in 1835, 1845, 1880, and 1907. 

An easy distinction between them is that the 1892 jail was built two years after Key West finished the county courthouse (using red brick ferried in from the mainland). The 1907 version was also less of a rebuild and more of an expansion, with a ten-foot-high wall added around the perimeter. 

Today, the fifth iteration, considered the fourth rebuild in 1892, is notable for its spectral presence. Within its porous brick walls, a pair of tragedies unfolded, forever altering its aura and making it one of the most haunted places in Key West. 

Key West’s Bloodiest Christmas

The holiday season is meant to be one of joy and happiness. Though meant to bring families and loved ones together, it’s forever a time of heartbreak for some. Going into Christmas 1921, Angela never could have guessed that her season would end in bloodshed and losing a loved one. 

Formed in the mid-to-late 18th century, the Ku Klux Klan had spread its influence throughout the United States. Klansmen had a heavy presence in the Keys, their venomous tendrils undeniably snaking through the local community. 

In December 1921, just before Christmas, Klansmen in Key West took note of a Spanish saloon owner (and World War I veteran) and his mulatto lover. 

The moment Manuel Isleño Cabeza appeared on the Klan’s radar, his fate was unfortunately sealed. Two days before Christmas, Klansmen kidnapped the tavern owner and beat him near to death. Reports state Cabeza was left with a ruptured kidney and had hot tar poured onto his skin.

Though in rough shape, Cabeza didn’t stay down for long. 

An Act of Revenge

Knowing that his life and, more importantly, that of Angela’s, was still in danger, Cabeza couldn’t let the incident go without retribution. Still recovering from his vicious beating, the islander exacted revenge against one of his assailants: William Decker. Cabeza tracked down the cigar factory manager and shot him, offering no chance for redemption for his vile act. 

Cabeza was picked up quickly by local law enforcement. Intending for the islander to face the justice system, the local government assigned Marines to guard the cell. Then, on Christmas Day, Sheriff Roland Curry relieved the Marines from their duty, leaving Cabeza largely unprotected.

Seeing their opportunity, the Klan struck again. While families celebrated the holiday, Cabeza’s body trailed behind a Klansman’s car. He was eventually lynched at East Martello Tower and ruthlessly peppered with gunfire. 

A Curse Upon Key West’s Klan]

The Klansmen made one mistake in their assault on Manuel Cabeza: They left Angela alive. A descendant with Afro-Cuban roots, it’s believed Angela practiced voodoo. Legend has it that the forlorn lover cursed the Klansmen responsible for Cabeza’s death. Afterwards, each died under suspicious and sometimes violent circumstances.

Cabeza may have finally gotten his revenge, but his soul had already been lost. It’s said that one of the specters patrolling the cells of the Old Monroe County Jail is Cabeza, trapped in the building meant to keep him safe until his trial.  

The Heartbreaking End of Osilio Perez

The Old Monroe County Jail is riddled with grief. That sorrowful energy has manifested apparitions of its former inmates, including an innocent man who had committed no crime. 

Whatever tormented Osilio Perez was never really known. However, it was enough to warrant him taking two attempts on his life. Both times, the 25-year-old Cuban immigrant was found in the woods, his wrists cut and blood draining from his body. 

To keep him safe, Perez was moved to Monroe County Jail. He was only meant to stay until he could be forced into an institution. Sadly, he hung himself using his belt when watchful eyes went to get him dinner.

Perez’s sadness remains unresolved to this day,

Apparitions of the Old Monroe County Jail

Preservation efforts became the focus of the Old Monroe County Jail in 2020. Though only a portion survived through the 20th century, restoration focused on making the jail accessible to the public, meaning that its chemistry was ultimately unchanged.

Whereas some historic buildings are torn down to make way for contemporary life, the Old Monroe County Jail freezes time. 

Within this bubble of history, ghosts of the past linger to remind us of their tragic ends. Manuel Cabeza and Osilio Perez remain fixtures of the old building. Disembodied footsteps or whispers cut through the silence. 

Haunted Key West

Key West is oozing with spectral history, from the unsettling doll who requires permission before taking a photo to the specters that lurk within the remnants of the Old Monroe County Jail. Secure your opportunity to explore the darker side of the tropics by booking your Key West ghost tour today.  

Brush up on your Key West haunted history by reading our blog. Care to know what specters lie in wait in Key West and beyond? Then be sure to follow us on Facebook, Instagram, or TikTok.

Sources:

• https://www.cityofkeywest-fl.gov/967/History
• https://www.hmdb.org/m.asp?m=243929
• https://archive.org/details/whiterobesburnin0000newt/page/64/mode/1up?q=key+west&view=theater
• https://www.unsettlingthings.com/key-wests-bloody-christmas-story/
• https://alisonfay.com/the-most-haunted-places-in-key-west-florida-that-you-cannot-miss/