Stone Walls Do Not A Prison Make

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The year 1776 brought the first crude mass attempt to burn a way to freedom. During the days of the mining operations a long drainage channel large enough for a man to crawl through had been blasted from the lowest floor level to the outer hill slope. The overseers had closed it with a massive oak door studded with iron. Attempts to break down the door or to chip away at it had proved fruitless, so the inmates decided to try burning it. Over a period of weeks quantities of kindling were smuggled below, a little at a time, until at last there was enough for a sizable bonfire. It was piled against the door, and a blaze was started with a flint. For a time the fire burned merrily as the flames licked at the wooden barricade. The prisoners were confident that the door would be demolished in an hour or two. But there was no one among them with a sufficiently scientific turn of mind to foresee the combined effect of the noxious fumes and the limited supply of oxygen. The smoke billowed along the ceilings of the cave. Gasping, hysterical men scrambled for air in lower chambers and found it thin. They clawed their way to the air shafts and were gagged there by the poisonous fumes. One by one they were overcome.

Above, the guards smelled smoke but were wise enough to know what a fire in the caverns would do to the occupants. They waited, and after the conflagration had died down of its own accord and the air had cleared, they carried out the dead and the unconscious.

After that unsuccessful attempt, all prisoners were jammed into the Jug while the drain was being plugged with stone and mortar, except for an air vent the size of an eaves trough. It was an unwise move, for in their anger over the congestion they set fire to the timbered ceiling, and all might have perished in the flames. But in the ensuing confusion the guards lost their heads—and lost most of their charges as well.

The number of Tories and culprits ready to take the place of any escapees seemed inexhaustible. The blockhouse was quickly rebuilt, stronger than ever, with a whipping stall, separate dungeons in the basement, and double hatchways at the main shaft entrance. Some thirty desperadoes were ushered through it into the caverns, and this was the group that staged Simsbury’s most famous break.

At the time, the confinement of the prisoners was so essential to the welfare of the country that the guard was increased to twenty-four privates under a corporal, a sergeant, and a lieutenant. The privates were required at all times to carry loaded muskets with bayonets fixed; the officers, cutlasses and pistols. There were almost as many guards as prisoners; they were cocky about their strength, and as undisciplined as they were confident. For once the custodians were almost humane, treating their charges with social deference and even permitting them visitors occasionally.

Abagail, wife of prisoner Jonathan Young, presented herself to the lieutenant late on the night of May 18, 1781. She begged permission to spend an hour with her husband, submitted to a careful search of her person, overlooked the ribald asides from the non-coms, and was cheerfully led by two of them to the hatch at the top of the shaft.

But Abagail’s call was not unexpected, either by Jonathan or his associates. It was part of a carefully plotted escape plan. On the ladder leading down the shaft were mounted most of the prisoners, armed with stones or any piece of metal they had been able to sneak into their quarters. No sooner was the hatch unlocked than strong arms from below heaved it upward, and the desperadoes poured forth. The officers were quickly overpowered, and their arms taken. Privates on night duty surrendered easily, and those asleep were given little chance to resist. Several prisoners were severely gashed by their own comrades during the scuffle in the dark, but by midnight every convict able to travel was over the hill. Behind them they left one dying officer, six privates stabbed or shot, and the entire company of jailers—regardless of their condition—locked in the dungeon. It was morning before the dash to freedom was known to the outside world, and by then it was too late to recover more than a handful of the escapees.

That break from what was often regarded as the strongest prison on the American side of the Atlantic was a painful embarrassment to Connecticut. The legislature was in session at Hartford at the time, and not a day was lost in starting an investigation. The most excoriating censure was expended upon members of the guard. “A young man more fit to carry fish to market than to keep guard at Newgate!” they flung at Jacob Southwell, who had had sense enough to remain out of the fray. “A small lad just fit to drive a plow with a very gentle team,” was the sarcastic charge cast at Nathan Phelps.

But that wasn’t the end of Newgate. With the same unyielding resolution demonstrated after other Revolutionary defeats, colonial officials once more patched up the prison and repopulated it; rough, tough, brutal guards were substituted for the lenient ones.