Today’s sordid history from Leavenworth Federal Penitentiary is the tale of Adolph Fein, the one-time vice-president of the Hebrew chapter of St. Louis’ Jefferson Club, a local organization of young Democrats that wielded considerable power throughout the state of Missouri at the turn of the century.

Fein was a well-known politician in St. Louis but as we will see, not very well-liked. His steady rise through the ranks of the state party was abruptly halted when he was indicted with Jacob Weissman in late 1903, for helping immigrants fraudulently obtain U.S. citizenship, i.e., naturalization fraud.

For a man accused of a felony, Fein did not appear overly anxious. He had been on trial twice before and emerged with no serious consequences for his behavior.

In a news article from January 1904 titled Fein Says He Will Peach, the Omaha Bee quoted a blustery Fein:

“I’ll tell the Grand Jury who the fellows were behind those frauds, and they were big fellows, too. When I was indicted, my friends said they would come to the front for me, and I made up my mind to keep my mouth shut, but they deserted me. I waited until December 27. Then I made up my mind that if they wouldn’t come to the front for me, the government would. So I wrote to Col. Dyer, the U.S. District Attorney, and told him I would give up everything I knew.”

Adolph Fein’s friends certainly came forward as promised, but they weren’t there to help their old friend out of a jam. Instead, his former colleagues, also vice-presidents of the Jefferson Club, testified against him. Ferdinand Schwartz told the court that Adolph had instigated all the wrongdoing. Frank Hertz said that Fein had repeatedly cajoled he and others to get involved in his racket. And William Novak said Fein gave him instructions to help create fraudulent papers.

It took three trials, but the law finally caught up to Adolph Fein. Late in the afternoon on November 5, 1904, a jury in the United States District Court convicted him of aiding and abetting naturalization fraud. He was sentenced to five years in prison, plus a $1,000 fine.

In 1905, St. Louis Post-Dispatch reported that Fein had been sent up to Leavenworth Federal Penitentiary, and the trouble started at once.

“Fein Feigned”: the newspaper’s editor has some fun with headlines

Upon arrival at Leavenworth, Fein convinced another prisoner that he was ill, blind, and suffering serious heart trouble. The other convict escorted Fein to the room where Deputy McClaughry was waiting to take his fingerprints. Despite the convict’s “strenuous” objections, McClaughry recorded his measurements on a Bertillion card, which was used with mugshots to identify prisoners. I’ll do a separate post on Bertillion cards soon.

Unfortunately for Adolph Fein, a Leavenworth doctor was on hand to examine him. He looked the new prisoner over, then he assured the deputy that Fein had excellent eyesight and was enjoying the best of health. McClaughry was not amused, and when Fein continued to insist he was really blind, the deputy sent him to solitary confinement for several days.

Adolph’s behavior grew increasingly strange. He continued to protest that he was blind and vague reports were heard back in St. Louis that he was a troublemaker. His hometown newspaper reported that Adolph was “most unruly”, and added with perceptible glee that his job while at Leavenworth was to “run a wheelbarrow”.

The guards told strange stories about Fein wandering around in a disoriented way, claiming he did not know who he was. Adolph continued to talk about his eyesight yet he had no trouble navigating the prison and the yard. They suspected he was trying to get out of work, and resorted to harsher treatment. The guards punished him by taking away his glasses and frequently locking him in solitary confinement.


Things began to change in 1906, when a different physician told the warden that Fein did have poor eyesight and could not work because he would injure himself.

In late March, Mrs. Adolph Fein received a letter from Leavenworth prison, informing her that her husband had been examined and pronounced insane. Three weeks later, a small blurb appeared in the Topeka State Journal that claimed Fein had been showing signs of insanity for the past six weeks, and had recently become violent. The article noted that Fein was transferred to an insane asylum in Washington, D.C., having spent about 5-and-a-half months at Leavenworth.

There were a few asylums in Washington D.C. at that time, but I haven’t been able to find out any more about Adolph Fein. It’s hard to say whether he was really insane, but I would guess he was — that prison just broke him, and his mind snapped. He had a very comfortable life in St. Louis and because he had more money and power than most, people indulged him, even if they didn’t like him. And he couldn’t tolerate his new reality – with the guards bullying him and being alone so much – so he retreated into a new world he invented for himself.

Leavenworth Penitentiary, the first federal penitentiary, was built in the late 1890s in Fort Leavenworth, Kansas.

The first 400 inmates were processed in 1903, and is still operating as a medium-security prison today. The prison and its surrounding wall – which extends 35 feet above and below the ground – was officially completed in 1926. Inmates sometimes call the prison “the Big Top”, a nod to its huge dome.

The prison’s early motto was Reformation, not Humiliation


The prison’s history has been punctuated with violence since before it officially opened. The prisoners from a nearby temporary jail were responsible for much of the initial construction, and several daring escapes took place in those early days.


A prison is, by nature, a wretched place filled with miserable people. Leavenworth has been home to several famous inmates including George “Machine Gun” Kelly, Carl Pazram, Bugs Moran, and Robert Stroud, the Birdman of Alcatraz.

The celebrity these famous men enjoyed may have alleviated some of the misery of the place. For the many anonymous prisoners, no such cold comfort existed. Take, for instance, the case of Inmate 2190, aka Bob Clark.

At age 24, he was convicted of breaking and entering a post office in Oklahoma, and sentenced to five years of hard labor, plus a fine of $500 (equivalent to about $12,900, in today’s currency). Clark, who was originally from the Texas town of Tyler, entered Leavenworth Penitentiary on June 3, 1900. By fall of the same year, he’d had enough of the prison life. Clark joined forces with 23 other inmates to plan an escape. He was a ringleader when the gang broke out of Leavenworth on November 7, 1900.

Seventeen inmates were recaptured a week later, but Bob Clark remained on the loose until December 6, when he and another prisoner were recaptured. The punishment was only a slap on the wrist: another 34 days was tacked on to his sentence.

Bob Clark was not long in making the news again. This time he was part of a group of five men, plotting to kill the warden and a guard, taking over an armory, and intercepting a train load of prisoners. The group was caught when a fellow inmate exposed the plot, but not before a guard was killed — though no one knew who fired the fatal shot.

Arrested in 1900; this mugshot was taken in 1909
Bob Clark mugshot, 1909

Now a confirmed and violent troublemaker, Clark wasn’t eligible for a light punishment this time. He was sentenced to life in prison for the guard’s murder. He was made a third class prisoner, which meant he was required to wear a striped prisoner’s uniform and shave his head.

His new sentence did not dampen Bob Clark’s longing to be back on the outside. By April of 1910, he was working in the prison’s carpentry shop. He and four other prisoners managed to hijack a train, when it entered the prison grounds with supplies. The inmates forced the engineer to ram through the prison gate, and fled across the prairie. Clark and another inmate peeled off of the group and ran into the woods, where they were recaptured.

On July 21, 1913, relief finally came in the unlikely form of President Woodrow Wilson. The president who had assummed office earlier in the year, intervened and commuted the sentences of Clark and three other prisoners who were serving life without parole.

This is as far as I’ve been able to trace Bob Clark. I wonder what became of him after he left prison. He was only 37 when he was released. I’d like to know if he was able to adjust to being on the outside or if he got in trouble again. For now, it’s a mystery.

Mugshots were still new at the turn of the century. The people pictured here were criminals but their names, deeds, and victims are forgotten. Their photos appear quaint, and could never be mistaken for those of modern inmates.

One interesting practice of this era was to allow prisoners to be officially photographed wearing hats. The hats tell us a lot about these prisoners: their occupation, their status, how much they cared about their appearance. Perhaps it was a wise trend. An escapee could cut or color his hair, for instance, but if he was a farmer chances are, he could be recaptured on a farm.

The following mugshots were taken at Leavenworth Federal Penitentiary:

Ben Porter

John L. McMonigle

Mary Grayson, 19 years old in the year 1900 Convicted of larceny

Francisco Salinas, age 39. Smuggler

B.M. Burris


Caesar Franklin, undated, Leavenworth

Leslie Isis, 1912 Leavenworth


This fellow’s name was Julius Ceasar:

Julius Caesar, 1905, Leavenworth


Prisoner at Leavenworth Federal Penitentiary

Sharper Grayson