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  • Writer's pictureLogan

The Lost Art of Jail Breaking

Updated: Apr 27, 2023

This month’s blog focuses on a phenomenon I had assumed only really existed in movies and books, or maybe in the old wild west: jail breaks. I just kept running into attempted and even a few successful ones as I was researching my original idea for a blog this month, and finally decided the other idea could wait. I had to get to the bottom of this. Why and how were people trying to escape, and how successful were they at evading the law? –Logan Janicki

The Lost Art of Jail Breaking

Nowadays, escaping from jail seems like a near-mythical feat. On the few occasions it does happen, it makes national headlines, and I would guess among most people today, the dangerous and daring prison escape is something assumed to have died out with the Wild West, save one famous exception from Alcatraz. Yet, by 1911, Illinois was certainly no longer the frontier, and as I began doing the research for my originally planned blog for this month, I was struck by just how many attempted jail breaks were reported in The Clinton Register in just one year. Clinton, and central Illinois generally, aren’t the most populous places, yet I found six reported attempted or successful jail breaks in just 1911, and I assume the same was the case in other years around the turn of the 20th century.

So why were so many prisoners willing to run the risk? This is an important question since most of the cases I found were not escapes from prison, but jails, meaning the (attempted) escapees had not yet even been sentenced, and could have walked away free men, with a little luck during their trial. The answer would seem to come in a report submitted early in 1911 by the Illinois State Charities Commission, which had conducted a survey of the state’s jails, following up on a similar report submitted forty years earlier in 1870, to see what improvements, if any, had been made to jails since then. “If any,” indeed: The report found no improvements in Illinois’ jails since the last report, and took particular issue with the treatment of prisoners, likening the jails to dungeons out of the dark ages. Disease was apparently rampant in the state’s jails, with the report condemning them as “disseminator[s] of foul diseases and tuberculosis,” which put the prisoners, staff, and visitors at serious risk of infection and death. The vast majority of people in these jails, if they were guilty, were liable to only be handed a fine or sentenced to a short prison term, yet simply waiting for their day in court risked them effectively suffering the death penalty. The jails were also called “schools of crime” by the report, and given the conditions, it’s no surprise they became a school for one crime in particular- jail breaks.

Still, other reporting in the Register paints a different story. A visit to the state penitentiary in Chester (near East St. Louis) by a Register reporter resulted in an excellent review of the institution. Most prisoners were well-behaved- they were aiming for parole, which earned them the newer, blue (for best-behaved prisoners) or grey (for second-best-behaved prisoners) uniforms, instead of the older, more demeaning striped black-and-whites. Escape attempts, the reporter also noted, were infrequent. Also, despite the poor state of Illinois jails generally, the DeWitt county jail was evidently a nice enough place for a wedding, as William Armstrong, son of the county sheriff, and Lois Sherburn held one there, which the Register called “impressive.”

There were also some compelling reasons to want to break into jail, rather than out, regardless how bad the conditions were. After all, for someone experiencing homelessness in 1911, with few or no institutions set up to provide assistance, jail could be the only option left to find somewhere to sleep. In one case in January 1911, Gordon Manning, desperate for somewhere to survive the sub-zero nights, intentionally got caught breaking into train cars in Decatur in order to stay in the comparatively safe city jail. Evidently thinking themselves wise to Gordon’s game, the Decatur police released Gordon the next morning, with the thermometer reading 0℉. However, wily Gordon easily checked this move, declaring as he left, “it is simply so cold I can’t stand it. I’ll have to do something to get in.” By the end of the day, Gordon had been arrested again on the same offense as the day before, safe from the cold another night.

Most escape attempts were just that-attempts, and were found out before anyone actually made it to the outside. The unfortunate thing is for any attempted escapee, breaking through a jail cell usually creates quite a bit of noise, no matter what method you might try. However, if enough people try sawing through the jail bars at the same time, as was happening in the Decatur jail in March 1911, there is some security in being part of a crowd. Even after conducting searches and finding 5 saws in the cell of Fred Patterson, deputies continued to hear prisoners hard at work each night, sawing away at cell bars and towards freedom. Likewise, some enterprising prisoners in the DeWitt county jail used the exercise time allowed in the hall of the jail to hide themselves and the noise of their work to break a hole in the jailhouse wall. They were only found out in September 1911 when some painters at work in the jail moved some screens and found the progress they had made.

Then as now, the 4th of July was one of the busiest days for the county jail in 1911, and so also, one of the busiest times for escape attempts. In the Macon county jail, “strenuous” attempts to escape the jail were made between July 7 and July 14, 1911 resulting in at least $100 in damages (almost $2800 in today’s dollars). The July 4 festivities seemed to be the perfect cover for a successful escape in Lincoln as well, as 15 prisoners made their way out of the city jail that night, though only one escaped recapture that night. According to the recaptured prisoners, all of whom were locked up for drunkenness or fighting that night, a stranger from out of town did the work of the escape, breaking an iron bar out of the chimney then using that to smash through the wall connecting the jail to the dog pound, then simply walking out of the pound into an alley through which he slipped away into the night, after which the rest followed.

Evading recapture is the final hurdle faced by would-be jail breakers, and by far the most difficult. After all, a jail break is only successful if the escapee is never recaptured. For example, when Fred Hurd arrived in Clinton in August 1911, police chief Heskett sensed something amiss about him, and consulting some wanted posters at the police office, realized “Fred” was actually Joe Watkins, one of the escapees from Decatur city jail “last March” (it’s unclear as to whether this meant March 1910 or 1911, and a quick search of the Registers for those months turned up nothing in either). With the Clinton police now aware of who he was, “Fred” was quickly found, arrested, and sent back to Decatur, now facing much more serious charges than when he was first arrested, due to his escape and long time on the run.

The lesson Joe may have learned then, and seemingly learned by most everyone in the 110 years since is that crime might pay, but jail breaks certainly do not. The most important factor in a successful jail break is luck, and it takes a particularly brave or foolish person to believe their luck will allow them to escape jail and live out the rest of their days, never to be caught and returned to a cell. Or, perhaps, no bravery or foolishness is needed to motivate escape attempts, simply jails so miserable, a state commission could mistake them for medieval dungeons.

Suggestions for Further Reading:

While it’s not reading, if you are interested in more local true crime, make sure to listen to the Vespasian Warner Public Library Podcast episode “The Courthouse Murder,” covering the dramatic trial of Isaac Wyant after he shot Anson Rusk dead in the county courthouse in 1855. Links to the podcast episodes on your platform of choice can be found here:

The Devil in the White City by Erik Larson covers perhaps the most famous criminal around the turn of the 20th century, H.H. Holmes, who is considered the first modern serial killer. It frames his crimes around the 1893 World Columbian Exposition in Chicago, and while a non-fiction book, presents the events it recounts in an engaging, novelistic style. It can be found in the library’s true crime section under True Crime->Murder->Serial Killers.

Piracy: The Complete History by Angus Konstam recounts the history of another mostly lost criminal art- pirating. The book covers the high-seas criminal profession from its earliest recorded days in the Bronze Age Mediterranean to the modern day and across the globe, from the Caribbean to the coast of China. The book can be found under True Crime->Piracy in the library.

The Bootlegger, by John E. Hallwas, covers the new age of organized crime that emerged in the era of prohibition, and how it profoundly affected even a small and remote western Illinois town. It provides an interesting contrast to this history blog, focusing on a period not 20 years later, and yet one in which American life was already significantly changed. It can be found under True Crime->Trafficking->HAL.

Finally, The Left Hand of Darkness, by Ursula K. Le Guin is an excellent and non-traditional piece of science fiction, focusing on the difficult work of communication and alliance between foreign cultures, and the novel culminates in a harrowing escape from prison. While not available at the library, it can be requested through inter-library loan, so simply call the library or ask at the desk for it to be put on hold, and we’ll get it shipped here for you to pick up.


“Broke Into Jail.” Clinton Register (Clinton, IL), Jan. 6, 1911.

“Fifteen Break Jail.” Clinton Register (Clinton, IL), Jul. 7, 1911.

“Illinois State News.” Clinton Register (Clinton, IL), Feb. 17, 1911.

“Jail Breaker Arrested.” Clinton Register (Clinton, IL), Aug. 18, 1911.

“Married in Jail Parlors.” Clinton Register (Clinton, IL), Feb. 24, 1911.

“Painters Deserve Reward.” Clinton Register (Clinton, IL), Sep. 22, 1911.

“They Had Saws.” Clinton Register (Clinton, IL), Mar. 17, 1911.

“They Want Out.” Clinton Register (Clinton, IL), Jul. 14, 1911.

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1 Comment

Tyler Petersen
Tyler Petersen
Nov 23, 2021

Great write-up! Loved looking at the sources -- whose wife would really approve being married in a prison? 😆

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