A Curious Account from the Penitentiary
Jack Kennedy and the Legions of Purgatory and Hell
Dr. Walter Hamilton published a controversial and now hard to find book entitled “The Legions of Purgatory and Hell: Being the True Story of Missouri’s Penitentiary” in the Fall of 1911. A practicing dentist at the time of publication, Hamilton had previously served 18 months in the Missouri State Penitentiary for the crime of larceny(theft of personal property). The third chapter of this rare book opens with a staggering 20 pages dedicated to his jailhouse friend, John F. “Jack” Kennedy.
I first stumbled upon mention of this book when browsing the State Historical Society of Missouri’s digitized newspaper collections. The September 7th, 1911 issue of The Republican published in Clinton, MO breifly describes Dr. Hamilton (here written as Dr. W. H. Shull for unknown reasons) and names the chapters of his upcoming book. It is a stroke of luck that they named the sub-chapters within chapter three titled “Some Remarkable Prisoners” as “Jack Kennedy, Train Robber” is the first mentioned prisoner. I tracked down a copy of the text held by the Missouri Valley Special Collections at the Kansas City Public Library Central Location.
At the time of publication, Jack was serving his final year in prison after being convicted of train robbery in 1899 and sentenced to 17 years in the State Pen in 1900. He was released via the 3/4th law in 1912. I will touch on the circumstances surround Jack’s one and only conviction at a later date, trust me it will take a few separate blogs to do it justice! My reason for writing about Hamilton’s book now, rather than when I cover Jack’s prison time, is because of the curious account of Jack’s early life featured within it.
Hamilton states that Jack was in charge of the heating, electric, and steam plant that powered the prison hospital. No doubt this is due to his experience with steam engines and mechanical systems as a train engineer. Jack and Dr. Hamilton became friends after sitting at the same table for meals all 18 months of Hamilton’s sentence. I want to preface everything else Hamilton details about Jack with two things: 1) Jack was a charismatic individual his entire life and his ability to exaggerate or flat out fabricate facts is well documented and 2) Hamilton has written perhaps the most gracious, endearing, and respectable account of Jack Kennedy that I have ever seen or heard and it has thrown me a bit.
Jack is described in these 20 pages as an honorable, god-fearing, selfless man that befriended all he met in the prison from guards to fellow inmates. The first example given of the Quail Hunters honor is that of his efforts to help his sickly former cellmate reach a pardon. Jack’s former cellmate had been in the prison hospital for some time and got word that his sister was close to getting him parole. As these things often went (and often still go) the act of getting a parole requires some monetary grease for the government wheels to turn. Jack gave the ill inmate every penny he had, then went and borrowed more money beyond what he had. No favor was asked in return nor was the money ever exptected to be repaid so far as we know. Jack’s cellmate and friend soon got his parole and left the prison in the company of his sister.
After highlighting this act of chivalry, Hamilton goes on to detail a saga of Jack’s early life that I’ve never seen mentioned anywhere else. The story goes that in 1885 at 17 years old Jack left the Kennedy farm in Crackerneck to work for a wealthy cattle rancher in Wyoming. In 1886 Jack and his employer were bringing some cattle back to the ranch when a group of sheep ranchers confronted them. A gun fight broke out and all were struck dead, except for Jack himself. The account goes into some detail of Jack’s reputation for being a sharpshooter and even states that his employer considered Jack a “moving arsenal or gatling gun when once put into action, with his unerring aim that always meant the center of his mark and death the coyote or wolf that happend to be within his range.” Jack’s skills as a gunmen are mentioned in a few other texts and, despite generally not shooting during his criminal career, isn’t something I cast doubt upon.
After this fire-fight, Jack was supposedly arrested and charged with two counts of murder to which he plead “not guilty” and was placed under a $50,000 bond. Now, that is a SUBSTANTIAL bond for the times especially given how frequently sheep and cattle rancher feuded and killed each other in that era. That would be roughly $1,661,340.43 today with inflation over 138 years. Hamilton states that the widow of the wealthy rancher that employed Jack tried to pay the bond but was denied due to some meddling by the sheep men. Bond having been denied, Jack was taken to jail. It is in jail where Jack meets a cattle thief from Mexico (the original text uses some unsavory language to describe this individual, which I will not repeat here). The cattle thief convinces Jack that his only chance of seeing freedom again is to coordinate a jail break with the help of his late employer’s daughter. Jack agreed and when the daughter and widow next visited him he instructed them to retrieve saws from Cheyenne and prepare horses nearby for their escape. They succeeded in their escape effort and fled on horseback into Mexico.
It is here where Jack’s story begins to look more familiar. Hamilton writes that Jack began working for a Mexican railroad as a fireman while waiting for the charges to drop against him in Wyoming. Once the charges were dropped as the state cracked down on the Range Wars of Wyoming, Jack moved up into Texas and took a job with the Souther Pacific Railroad. After this harrowing and likely fictionalized tale the chapter goes on to detail Jack’s move back to Kansas City and his being accused of robbing the Chicago and Alton trains in 1896 and the Frisco train in 1899 which landed him behind bars. Hamilton assures the reader that Jack was innocent of all charges and was wrongfully accused due to his proximity to the other outlaws of Crackerneck like the James and Dalton families. While I don’t agree that Jack took no part in any of these robberies, Hamilton presents a solid case when he highlights the number of robberies Jack was accused of during his time in prison. I myself have found a handful of newspaper articles stating that authorities from Chicago, New York, and other cities around the country were seeking Jack on charges of train robbery while he was safely locked in the Penitentiary. This apparently provided some entertainment for Jack as the guards would bring him telegraphs requesting his whereabouts so that he may be brought to trial.
Walter Hamilton’s intention in writing his book and in mentioning Jack’s story is clear. The Missouri State Penitentiary was a horrid facility filled with torture, violence against prisoners, wrongfully accused citizens, and conditons not fit for even the lowest of criminals. In telling Jack’s story, Hamilton is offering an example of a man treated unjustly by the system. He rightly points out that had Jack been a free man when the charges of train robbery were made he would very likely have been arrested and jailed. Does this mean Jack was innocent of all charges? Certainly not. Does it call into question how many of the alleged crimes Jack actually had a hand in? I think it must. Considering nearly all of Jack’s train robbery charges come down to his alibi and little other evidence, I can certainly see how it would be easy to wrongfully accuse him based solely on his reputation and a bad alibi. It always strikes me as odd that Bill “Whiskeyhead” Ryan (aka Bill Jennings) readily admitted his own guilt in the 1899 Frisco case but insisted for his entire sentence that Jack was innocent.
Hamilton ends his section on Jack Kennedy by once again advocating that Jack is an honorable, devout, loyal friend who has been mistreated and will make for a good and useful citizen upon his release. Who is to say if Hamilton is a reliable narrator or if he is prone to falling for the charms of a cunning outlaw? I am actively working with historians and archives in Wyoming to try and verify any of the claims in this book regarding Jack’s early life, but no luck so far. The account names no individuals beyond Jack himself and the only town mentioned is Cheyenne but it is never said if they are in Cheyenne or simply nearby. Surely a triple homicide involving a wealthy cattleman, a teenager from out of town, and a jail brake would have made the pages of at least one newspaper. We shall see!
I am gearing down my active research and collection of texts lately as I am preparing to actually begin writing Jack’s story in earnest. So while I can promise at least one monthly articles from this substack, beyond that will be hit or miss.
As always thank you for subscribing and please share this with anyone who may find it interesting! I write these blogs largely to collect my own thoughts on the research but also to introduce others to Jack’s little known tale.