Pensacola’s Escape Artist
In 1827, the Old Spanish Trail had been around for a long time…since the Spanish were in West Florida in 1559! It was the only road from Pensacola to St. Augustine. Everyone who made the trip took that route – traders, settlers, politicians, and messengers. Colonel Andrew Jackson even took it. It was later lengthened west to New Orleans, and then much later, when automobiles came on the scene, to California.
Thomas Jones was an official mail carrier for West Florida. He regularly made the trip from Alaqua (Walton County) to Pensacola and back again with bags full of mail. The well-worn trail was fraught with many dangers and obstacles, including deadly harassment from Native Americans, rivers & streams that had to be crossed, and wild animal attacks. Needless to say, the two-day trip was precarious, even for a veteran traveler such as Jones.
On July 14, 1827, while Jones was on the trail, he was approached by two men, one of whom had a gun and the other a knife. The man with the gun shot at Jones, missing his head by less than an inch, and the other stabbed at him, but only ripped his clothes. Jones managed to escape, flee to the nearest town, and report the incident.
A manhunt ensued. Identifying one of the attackers was an easy task for the officials, especially since Martin Hutto had committed such crimes many times in the past. He was apprehended, arrested and transported to the only jail in West Florida – the one in Pensacola.
The old jail wasn’t much. In fact, it was badly in need of repair. Vincent Pintado, a local mapmaker, had created a Pensacola map in 1813 which showed a “Public Prison.”
“How hard would it be to break out of here?” Hutto must have asked himself. “I don’t know, but I might try it.”
This jail, located at Alcaniz and Intendencia Streets, was recorded in a local newspaper in 1827 as being in deplorable condition. Therefore, it was no surprise when it was discovered that Hutto had escaped. On September 5, 1827, a reward of $80 was offered for his apprehension. He was suspected of fleeing to Butler County, Alabama.
In November, Hutto voluntarily turned himself in, anticipating an acquittal when the judge came 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 of 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 shore of Bayou Chico.
Hutto escaped from the Army jail on Jan. 23, 1828. A reward of $30 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. A fifty-dollar reward was offered this time. Hutto was recaptured and returned to Pensacola in October 1828 where Judge Brackenridge sentenced Hutto to two years in prison.
On March 27, 1829, Hutto escaped for the fourth and last time – this time also from the Pensacola jail, never to be heard from again. The city fathers finally realized that they needed to address the problem of the old jail.

Interesting. Like your stories.