Pensacola’s Old Jail

By Mike Simmons

Joseph Purcell was a Irish cartographer, also known as a mapmaker. In the late 1700s, he was part of the British government and worked out of Pensacola, making maps throughout the southeast.

There is an old map of Pensacola drawn by Purcell in 1778. It was titled, “A plan of Pensacola and its environs in its present state, from an actual survey in 1778.”

The map shows that, at the time, Pensacola consisted of a fort on the bayfront that extended from present-day Government Street to Main Street, which ran along the edge of Pensacola Bay in those days. It also extended from present-day Palafox Street to Alcaniz Street. Outside the fort were houses scattered two to four blocks north, east and west.

On the map is a block labeled “C” located at the southwest corner of today’s Alcaniz and Intendencia Streets. The “References” list “C” as being the “Gaol,” which is the Spanish word for “Jail.”

It is not known when the jail was built, but it is safe to say a jail has been in Pensacola for many years.

A jail was there, but what kind of jail was it? Was it big? Probably not. Was it unkempt? Probably. Was it safe? Doubtful. Was it secure? I doubt it.

Was it maintained? Well, if it wasn’t, it was in poor condition 49 years later when it made the news.

In 1827, the Old Spanish Trail had been around for a long time – at least since the Spanish were in West Florida in 1559…and probably before that! It was the only road from Pensacola to St. Augustine. Everyone who made the trip took that route – traders, settlers, politicians, and messengers.  General Andrew Jackson took it. Later, as US Highway 90, it was lengthened west to New Orleans, and then later to California.

Thomas Jones was an official mail carrier for West Florida in 1828. He regularly made the trip from Alaqua (Walton County) to Pensacola and back again with bags full of mail.

At the time, the trail was not the nice highway corridor it is today. The well-worn trail was fraught with many dangers and obstacles, including deadly harassment from Native Americans, and wild animal attacks. Imagine having to cross the Escambia, Blackwater, Yellow, Shoal, and Choctawhatchee Rivers, besides the streams and swamps. Needless to say, the two-day trip was precarious, even for a veteran traveler such as Jones.

Mail carriers were lifelines of the frontier. They carried government dispatches, legal papers, newspapers, money, and personal correspondence. They were unarmed or lightly armed, predictable in schedule, and traveled alone. That made them targets.

In 1827, Jones was riding eastward along the Old Spanish Trail when he encountered two men – one armed with a gun and the other with a knife. The intent was not only to rob Jones, but to kill him. When the pistol was leveled at him and fired, Jones must have felt some relief, because the lead missed his head by inches. The knife-wielding bandit stabbed at Jones and sliced up his clothes, but he was not severely injured. He escaped to the nearest settlement, probably Milton, Holt, Crestview, or a nearby community.

“Oh, that’s Martin Hutto!” came the reply from the townspeople. “He’s just plain mean. He has done that before.”

But he hadn’t tried to rob and kill a Federal Mail Carrier. That was different. Even in the frontier towns along the untamed west Florida territory, this was uncalled for. Posses formed and lawmen were summoned. Before long, Martin was located and taken into custody.

But…where to take him? The small frontier communities had no jail. Most were only a collection of houses, and maybe a store. The only place that had a lockup facility was Pensacola, the largest town in West Florida. So the lawmen and Hutto headed there.

The old jail wasn’t much.  In fact, it was badly in need of repair. After Purcell’s mapping of Pensacola and the jail in 1778, Vincent Pintado, a local mapmaker, created another Pensacola map in 1813 which showed a “Public Prison.” So, in 1827, the jail, still there, was old, and probably decrepit. The same year that Hutto was locked up there, the old jail was described in the Pensacola newspaper as being “in deplorable condition.”

“How hard would it be to break out of here?” Hutto must have asked himself. “I don’t know, but I might try it.”

Therefore, it was no surprise when it was discovered that Hutto had escaped. On September 5, 1827, a reward of $80 ($2900 in 2026) was offered for his apprehension. He was suspected of having fled to Butler County, Alabama, 120 miles away.

In November, Hutto voluntarily turned himself in, anticipating an acquittal when the circuit judge rode into town later that month and held court. Unfortunately, Judge Brackenridge did not come for his usual November hearings, so Hutto had to wait until May,1828. Fearing that Hutto would escape again, he was held in the military jail at the US Army camp known as Cantonment Clinch, located on the banks of Bayou Chico – west of town.

But it happened anyway. Hutto escaped from the Army jail on Jan. 23, 1828. A reward of $30 ($1000 in 2026) was offered this time. Hutto was quickly recaptured and stood trial on May 7, 1828. He was convicted by the jury and held in the Pensacola jail while awaiting sentence. On May 15, Hutto again escaped and headed to Mobile, Alabama. A fifty-dollar reward was offered this time. Hutto was recaptured and returned to Pensacola in October 1828 where Judge Brackenridge sentenced him to two years in prison.

Local history passed down (no documentation) says that on March 27, 1829, Hutto escaped for the fourth and last time – this time also from the Pensacola jail. Records never show that he was seen again. The city fathers finally realized that they needed to address the problem of the old jail.

References: Pensacola Gazette –

1827: 09/14, 10/03, 10/18, 10/19, 10/26, 11/02, 11/09

1828: 01/25, 05/23, 05/30, 06/10, 06/17, 06/24, 07/01

Pensacola News Journal – April 7, 1974

Interesting…