AJ Schenkman: Ulster County Jail Breaks

The court house in Kingston is one of the many historic buildings in an area commonly referred to as the Stockade District or Uptown Kingston. This court house has stood at the present location in some form for centuries. It is not only linked to the founding of New York State in 1777, but also to Sojourner Truth. It was in this court house that she successfully sued for the return of her son Peter.

It also contained the jail, until it was replaced by another building. These two jails were where some of Ulster’s more notorious criminals were housed awaiting trial or serving out sentences. Equally interesting for the individuals the jail once housed are some of the more interesting ways in which those housed in the jail tried to escape.

A rich source for those that escaped the Ulster County Jail is the newspapers of the time. It is important to point out that prisoners did not escape often, but when they did it made headlines. More times than not, those who absconded were apprehended by the “sleuths” of the same period such as Ulster County Sheriffs Zadoc P. Boice, “Fearless” Phil Schantz, and Deputy Sheriff William Cohen to name a few in the long history of the Ulster County Sheriff’s Department. One inmate, in 1903, had the distinction of “being the first attempt at a break out since the new jail was erected and the old jail repaired.” She did not quite make it out of the jail but came close.

Jennie Green was being housed in the women’s part of the jail. How she was able to obtain a “clasp knife” is not known. She did realize at some point, while awaiting trial, that all the walls which surrounded her were not reinforced with steel. With plenty of time to think and observe Green realized that the one outside wall was made of plaster and lath. A sharp blow from her tool confirmed it- she went to work.  Once she cleared the plaster and lath away, without at first being noticed, all that separated her from freedom was a ‘seven to eight inch thick wall.” It was made up of small stones. Once again with tool in hand Green worked the stone.

Jailer Carman, according to a local newspaper, became aware of an abundance of “falling mortar.” He went up to investigate. As he neared Green’s cell he continued to hear a digging sound, and when he looked into the cell there was plaster and mortar all over the floor. He watched for a period of time as the inmate was so consumed with digging out that she neglected to realize that she was in fact being watched by the jailer. He entered the cell and placed her in a more secure cell until her arraignment the following day.

The week of August 22, 1897 was a warm one. When it became hot the jail also heated up to a point that it became very uncomfortable for the prisoners being housed. Jailers, in order to show some compassion, allowed inmates to sleep outside their cells in the jails corridors. Once the jail settled down for the night, and they were sure the jailer was asleep, four prisoners implemented their escape plan.

Joseph Decker, William Lasher, John Boylan and Charles Sullivan somehow secured a saw to help them escape. When the jailer was asleep they went to work on the iron bars inside and then the second set of bars on the outside wall at the rear of the jail. How they did not awake anyone with the sawing is hard to believe. Jailer Smith was surprised when he was awakened by a prisoner who informed him that four prisoners had escaped last night.  Jailer Smith went to investigate and found that four bars on each side of the wall had been cut revealing a “fourteen inch square through which the prisoners escaped. All four men lowered themselves from the second floor using a blanket.

There are other interesting jail breaks such as the one lead by an individual named Thomas Cosgrove. He managed to pick the lock on his cell with a broken broom handle because the safety had not been set on the lock. All three escapees were quickly apprehended. One of the three convicts was apprehended in Albany while doing his laundry on the banks of the Hudson River.

In at least one incident a man named Charles Johnston made a name for himself at the new jail completed in 1903. He was so inebriated that he actually tried to break into the new jail. He got as far as climbing the fence that encircled it when he was caught by a guard. The Kingston Daily Freeman reported that the following morning he did not have to worry about breaking into jail again because he was safe and secure having been given a sixty day sentence.

Photo Provided by Lisa Spada-Bruck 

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