The very first escape attempt

The wounding of Larned Upshaw, who possessed black devilish eyes, gave the state penitentiary a bad start and caused a deficit in its operation. Upshaw was the first prisoner shot at the new penitentiary. In 1836 there was an overseer who supervised making of brick, his assistant, and one guard, plus the warden. Warden Bolton said from the start that the staff should make at least six hundred dollars a year and the guard two hundred dollars a year.

When Upshaw made a desperate attempt to breach over part of the wall and refused to be retaken he was shot. The penitentiary then went into debt. The first year the prison had a deficit of $250.00 because a man had to be hired from the outside to take the place of the seriously wounded Upshaw.

Warden Bolton stated, "Servant hire has somewhat increased our expenditures. About the time we get into successful operation, in making brick, one of the convicts (Upshaw) scaled the walls of the penitentiary and attempted to effect his escape. He refused to be retaken until he was shot. The wound so disabled him as to render him unfit for services afterwards. We lost his labor and had to hire a hand in his place. Making brick will be the most profitable employment for the convicts during the next two years."

Earliest documented homicides and escapes, June 1841 One of the earliest documented homicides and escapes from the penitentiary took place in June of 1841. A group of convicts plotted to kill their overseer, Mr. William Bullard, while lessees Burch and Gordon and a number of the guards would be away from the prison. Shortly after the noon meal, three convicts who worked in the saddle shop summoned Bullard under the pretense of inquiring about their work. As soon as he entered the room, one asked him a question to divert his attention while another struck him a mighty blow with a mallet. After several more blows proved fatal, the group grabbed his keys and two pistols.

The gravestone of William Bullard, the first prison employee to lose his life in the line of duty.

They headed toward the gate and along the way picked up a few more prisoners eager to make a getaway. Nine succeeded in slipping free of the walls. The alarm was immediately sounded, and citizens managed to capture one of the men who was sick and unable to keep up with his comrades. The other escapees hid in the deep ravines near the river until nightfall when they managed to sneak away to freedom. Eventually, a prisoner was caught and charged with the murder of Bullard. Although he defended his innocence to the end, he was hanged outside the wall. William Bullard, the first officer killed in the line of duty, is buried in an obscure location in the Old City Cemetery in Jefferson City.

Escapees Terrorize Town

By 1868, the population of convicts had grown to 735. Many of them worked outside the walls, and once again, escapes were a common occurrence. One convict escaped and stole a citizen's horse to make his getaway. Others terrorized the citizenry. Townspeople armed themselves to the teeth in order to protect their families. In 1869 a spectacular and terrifying story made the headlines; an underground passage was discovered reaching nearly under the wall. It had been detected just in time. The townspeople shuddered at the lurid prospect of 700 loose convicts robbing and ravishing at will. Public outcry demanded that something be done about the prison.

Convicts escape by Train 1870: Some convicts successfully gained their freedom by jumping on board freight trains. The prison guards complained that the trainmen of the Pacific Railroad were intentionally encouraging the inmates to escape. Guard J.P. Raithel testified: I have seen the managers of the train throw apples to the convicts and motion at them. When I arrived at the train, the managers seemed to be angry. I think I would regard the motions made by the trainmen as being friendly to the escape of the prisoners.

Notices were placed in local newspapers when convicts escaped from the penitentiary.

A popular escape trick is attempted

While news of an escape from the penitentiary or from a convict work detail always made headlines, some prisoners never even made it as far as Jefferson City. Others had better luck before they even reached the penitentiary with the "water closet dodge." Two Vernon County prisoners were en route to the penitentiary by train. After they had traveled some distance toward Jefferson City, they complained that their leg irons were hurting them. An officer removed them and fastened them over the convicts' coats, instead of over their wrists. Later, the two asked permission to go to the water closet of the car and were allowed to do so. The officer remained outside and waited. Prosecuting Attorney C. L. Davis, who was accompanying the men, warned this officer:

"That is an old trick to escape. Better look in on them."

The officer did, and sure enough, the two prisoners had easily wriggled out of the wrist restraints, opened a window and leapt out. As the train was only traveling at half speed at the time, the pair escaped unhurt. By the time the train was stopped and men sent back to look, the convicts had disappeared into the thick forest.

Four convicts make an attempt at freedom During April of 1904, four convicts made a desperate attempt at freedom. Somehow, they had managed to obtain three revolvers and a quantity of dynamite, with which to blow the hinges off doors that stood in their way.

Harry Vaughan, Edward Raymond, and George Ryan.

Someone had warned the officers that an escape was planned, and at the appointed time, the four men were noticed out of their cells and moving furtively toward the door. Guards immediately surrounded them. Convinced their effort was now futile, the four gave up at once. The existence of the guns and dynamite worried the guards, who wondered how such items could have ended up inside the walls. The inmates themselves told differing stories: one claimed it had been dropped down inside the walls to them; another that they had received it through the mail. Prison officials feared that the real culprit was someone who worked at the prison, who had carried the guns and explosives in to them.

Deputy Warden R.E. See.

The very next year a similar escape attempt was made, this one nearly successful. At 3 o'clock in the afternoon of November 24, 1905, four prisoners met at the stockade gate. George Ryan handed out Colt .44 revolvers and a large supply of ammunition to fellow convicts Harry Vaughan, Edward Raymond and Hiram Blake. The four then entered the office of Deputy Warden R. E. See, and he was ordered to put his hands in the air. Instead, he went for his gun and one of the men shot him in the shoulder. After See slumped to the floor, he and another person in the office were grabbed and used as shields for the men as they raced across the yard toward a large iron gate that led outside the prison. Guard John Clay was gatekeeper the day the four desperadoes hollered at him to hold up his hands. While in this vulnerable posture, one of the four shot him in the head, killing him. Another guard, Ephriam Allison, noticed the commotion through a grated door and yelled, "What's going on there?" He was shot twice and also fell dead.

The escapees then placed a charge of nitroglycerin on their last remaining hurdle to freedom, a large gate at the end of the driveway. It blew the lock completely off the gate and made a jagged hole large enough for the men to dive through. The four ran down along the railroad tracks toward the depot, shooting back at the pursuing guards. One of the fleeing prisoners, Hiram Blake, was shot and killed by police officer John Bruner.

The remaining three jumped in a wagon belonging to Houck McHenry and held a gun to the driver, Arthur Lane. Using him as a shield, they grabbed the reins and whipped the horses to a full gallop. They raced down Madison Street south to Dunklin; then turned west on Dunklin. In front of the Capital City Brewery, Ryan fainted from sheer fright and fell off the wagon. Vaughan and Raymond kept going, until a young boy, Emery Green, bravely ran into the street and grabbed the bridle of one of the horses, stopping the wagon. Vaughan leapt from the wagon and tried to shoot the boy, but his gun wouldn't fire. Policeman George Staihr, gun drawn, apprehended the escapees.

The murderous trio being prepared for execution.

The three convicts were returned to the penitentiary and placed in solitary confinement. George Ryan confessed to the escape plot and told prison officials that the guns, ammunition and explosives had been brought to them by an ex-convict, H. E. Spencer.

Newspaper account of the escape, murder, trial and execution.

After a series of trials and appeals, the Missouri Supreme Court on May 16, 1907, finally found the three guilty of murder in the first degree and sentenced them to hang. Ryan was upset by the verdict, as he felt he should have been treated more leniently for confessing the details of the escape plot. Dressed in suits, the men were hanged, side-by-side, on June 27, 1907. The hanging took place in the Cole County jail yard on Monroe Street in front of a huge crowd. The Cole Count Democrat (June 27, 1907) ran this headline: "Jerked To Eternity." The article claimed that thousands of spectators stood on hilltops and roofs around the jail and noted, with some consternation, that women, as well as men and children, had gathered to watch the execution. "It certainly seems a gala day for the morbid ..." it reported, then described in macabre detail the death struggles of the three men.

A close-up view of prison officials preparing Harry Vaughan for hanging.

Left to right: Edward Raymond, Harry Vaughan, and George Ryan, hooded, awaiting death. Father Henry A. Geisert, MSP's Catholic chaplain appears in line after Ryan.

After the drop, it reported,"Vaughan's neck was broken by the fall, and he did not quiver. Ryan gave evidence of suffocation while Raymond strangled to death. Although Raymond struggled the most he was the first to be pronounced dead." As for the men murdered in the trio's escape attempt, Governor Joseph Folk spoke at Officer Clay's funeral as he was buried in the Woodland Cemetery on McCarty Street in Jefferson City. Officer Allison, not from Jefferson City, was buried in his hometown. The legislature approved paying $2,500 each to the widows of the slain guards.

Guards man towers to prevent escape over the wall There are thirteen watch towers. These guard stations are numbered, and each guard has a peculiar signal, by a special toned whistle, by which he talks to the central office. Some of these towers are very picturesque, and at a distance must resemble the old feudal castle towers of the old world. Each guard is heavily armed to prevent escape via the wall route. These guards are always on the lookout, both day and night, and are the real thing. They are divided into two watches of twelve hours each.

One of the many castle-like towers atop the wall at MSP. This one is located above the "wagon gate", an entrance situated at the end of Lafayette Street.

An early version of the guard towers that dotted the wall at MSP.

One industrious convict escaped in 1916 using a method that had never been tried before. Convict George Smith, a lifer serving a murder sentence, hid from officers one morning as they escorted the breakfast line to eat. Smith took a sixteen-foot scantling and dragged it to the east wall. In a feat of extraordinary strength, he climbed hand over hand to the top of the wall, scrambled over, and dropped to the ground below. It was a steep drop, but he escaped injury. He then raced for the railroad track and was long gone before discovered missing from his prison factory job.

Amazed prison officials could only shake their heads. The Jefferson City Democrat Tribune dubbed Smith the "Human Fly," and called his penitentiary getaway a "remarkable feat."

Well Planned Escape Costs Captain's Life In February 1918, as reported in The Daily Capitol News (March 1, 1918), Captain Eli Jenkins was in charge of B-Hall and was responsible for waking up the prison cooks at 4:30 in the morning so they could begin making breakfast.

B-Hall, the sight of the murder of Captain Eli Jenkins.

On this morning, he rapped on the door of a cell shared by David Bartlett, Kenneth Brewer and Jacob Goss. Pretending that Goss was ill, the other two asked Captain Jenkins to have a look at him. Jenkins stepped into the cell and immediately the two overpowered him, stabbing him in the heart with a large butcher knife. They grabbed his keys and threw his body into a corner of the cell. Goss was left bound and gagged on his bunk. The desperadoes rushed toward the east stockade wall, which they breached and escaped to freedom. Another prisoner, Joe Kenney, escaped with them.

A photo of J.M. Buck Williams.

The three were soon apprehended in Sedalia and Officers Buck Williams and Jim Hoover were dispatched to bring them back to the penitentiary. While awaiting trial for murder and escape, they were placed in special receiving cells away from the regular population for fear that angry mobs of convicts might do them harm. Captain Jenkins had been well-liked. He was described as kind and considerate. A former teacher, he volunteered to teach in the prison school and his death was mourned by many of the convicts. The other prisoners were deeply ashamed of the actions of their "brothers" and threatened to string up the three if they ever caught sight of them at large in the prison proper. In his confession to the members of the prison board, Dave Bartlett admitted that he had killed Jenkins, but said he only meant to stun him:

I had a piece of lead pipe about two feet long, and with this, I calculated that I could beat Captain Jenkins into insensibility and then we could make our getaway. (When Jenkins entered the cell) I struck him with the lead pipe. He made a noise and commenced drawing his pistol. I struck him again, but was not able to knock him senseless and believing that he would shoot me, I drew a knife and stabbed him. I was badly excited, but I believe I only stabbed him twice. I did not know how badly he was hurt.

I told Brewer to take his keys and let Kenney out of his cell to go with us. We then left the building, and used boards in getting over the first wall from the outside. We went down the ladder from the guard house and straight across the playgrounds to the outer wall. We used boards in getting on top of this wall and from there we jumped to the ground.

We climbed on the fast mail train at the station about two minutes before it started and occupied the space between the fender and the blind baggage until we got to Sedalia. When the train slacked up there, we jumped off and hid in a vacant building until about ten P.M. Then we made our way to the station and were looking for a freight going west when the police pounced on us and the game was up.

Escape in the Missouri River

On a bitterly cold January afternoon in 1926, one of the most desperate attempts ever to escape the penitentiary made headlines. Two convicts, Carl Pittman and Fred Hildebrand, were working at the machine shop. While the guard had his back turned, the two grabbed a ladder and, quick as a flash, were up and over the wall. Guards on towers 11 and 12 saw the two leap to the ground and opened fire on them as they raced toward the river. They alerted other guards who pursued the escapees with shotguns. Hildebrand reached the river first and began gingerly walking across the ice cakes. Pittman jumped into the icy water and swam toward a cake, clinging to it for dear life. The guards on shore fired their weapons, yelling and cursing. When the two convicts had made it halfway across the river, the current suddenly caught the ice cakes they were riding and swept them back to the prison side of the river. The guards raced alongside them, finally catching up where Prison Farm No. 1 bordered the river. By now, the freezing, exhausted convicts gladly reached for the sticks held out to them by the guards. One of the men was near collapse and was slipping from his ice cake as he was rescued. Both men were bundled in blankets and rushed to the prison hospital in serious condition, with frostbitten hands and feet.

Later, the two said they had hoped to reach the opposite side and hide in the willows until nightfall. Except for the tricky current, they might have been successful.

Escape attempt thwarted

Another escape attempt was thwarted in June 1926. Three convicts leisurely walked out of Factory No. 6, and approached the wall. They had walked out with a rope that had heavy pieces of metal attached to one end. They hurriedly threw the rope over the wall and the metal pieces acted as grappling hooks, catching between the bars of a tower. They climbed to the top and jumped down, landing on Lafayette Street.

A car owned by Lafe Copas was parked along the street, and the three inmates got in. A city councilman, Louis Juttemeyer, was about to climb into his car when he noticed the three suspicious men dressed in inmate garb. He waved his arms and hollered to get the attention of the tower guards. The desperate escapees tried to start the car as the key had been left in it, but it wouldn't start. One of the convicts, Joe Endalee, tried to make a run for it. Two tower guards, C. E. Kustard and Alex Hornbuckle, shot Endalee twice and pinned the other two down until they could be apprehended.

Walter Holub escapes through sewer pipe

One man, whose idea to leave town in 1924 was a little premature, earned a place in escape history. While most escape attempts had been made by convicts out on work detail, or were carefully planned strategies to scale the wall or storm the gates, Walter Holub had a different idea. Holub had been sent to clean out a sewer pipe that lay within the prison. Not caring much for doing the assigned job, he stuck his head into the sixteen-inch pipe and wriggled his way to the outside where he emerged, coated with sewage. He managed to make his way out of Jefferson City and, in fact, entirely out of the state. He was apprehended in Denver, Colorado, six months later after robbing a drugstore.

James Hart, guard is killed during escape

Three other inmates plotted an early morning escape on February 4, 1924, with more tragic results. After sawing through the iron bars of their cell, Frank Delcore, Jack McFall, and Miles Thomas attacked a guard, James Hart, clubbing him on the head and then tying him up and gagging him. Hart never regained consciousness, apparently dying by strangulation. The escapees took Hart's gun and used a ladder left at a construction site on the grounds to climb the wall on Lafayette Street. After exchanging fire with the guards, they darted through yards across Capitol Avenue to freedom. Bloodhounds were brought immediately from Sedalia but could not track because of the rain, sleet and snow. After an identification and arrest in Hermann, Missouri, was determined to be false, two truckloads of guards were dispatched to investigate a reported sighting from a farmer two-and-a-half miles from the prison on Wardsville Road. The officers searched the barn and outbuildings and then began walking the property. Dusk arrived with blizzard conditions.

According to one newspaper account, footprints in the snow led the guard posse to a straw-stack in a cornfield behind the farmhouse. One of the officers picked up a gunnysack that was lying on the straw and a burrow was revealed into which the officer shone the beam of his flashlight. Delcore, apparently the trio's leader, fired the remaining bullets in Hart's gun, failing to hit any of the officers. After a momentary lull, the guard captain gave a signal and the officers opened fire on the stack of straw. At the end of the cold, exhausting day, the dead inmates were hauled to Heinrichs' Undertaking Parlor where an estimated one thousand people streamed through the next day to get a look at the bullet-riddled bodies. Officer James Hart was laid out in the same parlor as the escapees.

The three officers on the south wall the morning of the escape were suspended from duty while their actions, or lack of them, were investigated. The paper reported that any action would wait until Warden Crawford returned to work from his home in Carrollton where he had been confined by illness.

Convict assaults guard in escape attempt

December 30, 1929, Jefferson City Post Tribune headlines would deliver a more sobering report that struck fear in the hearts of the prison's neighbors. According to the article, on that day, John T. Bradley, a seven-year veteran prison guard from New London, Missouri, was stabbed and clubbed as he fought on top of the perimeter wall with two convicts bent on escape. Another guard shot one of the men but Clarence Hansen escaped with Bradley's revolver. Guards pursued him on foot but he eluded them. It proved a good idea when Curtis Quimby, an attorney living nearby, got a gun and flashlight before investigating a noise he heard in his basement. Quimby found Hansen hiding in a fruit closet and was beseeched by the escapee for a break. Prison officers were summoned by Quimby's wife. Officer Bradley had been rushed to St. Mary's Hospital where doctors determined that his injuries were not life threatening, according to the newspaper account.

3 inmates hatch daring plan to escape In February of 1949, three penitentiary inmates hatched a daring plan. They would saw through the bars of their cells, scale the mighty stone walls using a homemade ladder, and swim across the Missouri River. Emerging at the municipal airport directly across the river from the prison, they would steal a small plane and fly to freedom. Unfortunately for them, a sharp-eyed guard spotted their makeshift ladder constructed from scraps of lumber, hidden in an untrafficked area of one of the prison shops. The plot was completely foiled when Yardmaster Bernard Poiry intercepted a note written by one of the three. In it, the escape plan was outlined.

A prisoner's back-up card with photo, name, crime, and escapes. This convict escaped October 3, 1946.

Death row inmates attempt escape June 24, 1962 Subject: Attempted escape—Death Row To: Mr. W. P. Steinhauser, AW-C I went on duty at Death Row at approximately 5:30 P.M. Nothing seemed to be out of order. At about 6:00 P.M. a couple of the Death Row inmates asked me to sharpen some pencils for them. I took them into the Receiving Unit office and sharpened them, and returned them to the inmates. Then, at about 6:15 P.M., an inmate on the far side called to me. I went around to see what he wanted, and Thompson and Williams, who were out of their cells, seized and overpowered me. They put me in Thompson's cell; removed my clothes, tied my feet, and also my hands behind me. After about 30 or 40 minutes, they carried me to Anderson's cell and put me in there. By this time all six Death Row inmates were out of their cells.

Lloyd Leo Anderson participated in the escape attempt from death row. He was executed February 26, 1965.

Sometime later, around 8:00 P.M. the telephone rang. They untied my feet and took me to the phone to answer. It was the Control Center asking for inmate Kurtz, I.D. clerk. I told them he was not there.

A little later I heard one of them say 'There they are, we might as well give up.' Then Sr. Guard Charlie Bosch started rapping on the door.

Charles H. Odom wore Guard Earl Snyder's uniform during the escape attempt.

They untied me, I put on my clothes. Let [sic] Sr. Guard Bosch in, and they all returned to their cells. Inmate Odum [sic] had put on my uniform shirt and cap and impersonated me so that the tower guards, looking through the windows would see nothing wrong. As I was tied and in a cell most of the time, I could not see their activities, and did not hear them make much noise, although they did break through several locks. The TV was turned up loudly during this time. Sr. Guard Earl Snyder 3-11 Shift.

James Earl Ray Escapes James Earl Ray began a record of scrapes, big and small, with the law serving terms in Joliet and Pontiac prisons in Illinois, and Leavenworth Federal Penitentiary in Kansas. On October 10, 1959, Ray and James Owens, an ex-convict, held up a Kroger store in St. Louis. Ray was given a 20-year sentence at MSP.

James Earl Ray, MSP escapee. Later assassinated Dr. Martin Luther King, Jr.

Charles H. Odom wore Guard Earl Snyder's uniform during the escape attempt.

A few months into his sentence, Ray made an unsuccessful escape attempt by climbing over the wall on a homemade ladder that collapsed. Five years later, he made it to a roof before being spotted. He became well-known as for his ability to disappear for days on end inside the prison. On Sunday morning, April 23, 1967, Ray's escape plan worked. Reporting to work early in the prison bakery, he was helped into one of the large boxes used to ship loaves of bread. A truck from Renz Farm drove in to pick up bread and Ray rode out of MSP in the bread box, escaping from the truck somewhere between MSP and Renz Farm.

Inmates Get Guns To Escape

On Saturday, July 25, 1981, two inmates tried to escape from MSP using a cutting torch to cut bars on a door. Surprised by two officers, the inmates pulled guns and took the officers hostage. A third officer summoned to the scene was taken hostage as well. During a tense five hours, the inmates threatened to kill the officers if their demands were not met.

One of the inmates was serving two life sentences for murder; the other was serving ten years for burglary and stealing. They demanded that they be taken to another Correctional facility. When Corrections officials agreed, they released their hostages and surrendered peacefully. The two were temporarily relocated to the federal medical center prison in Springfield, Missouri.

Later investigation revealed that an MSP employee had smuggled the two handguns and cutting torch into the prison.

The entrance to the tunnel under the chemical plant; the the two tunnelers in custody. Warden Bill Armontrout yelled into the hole, "We're gonna start fillin' the hole with concrete if you don't come out!"

Two Inmates Dig A Tunnel Over the years, many convicts attempted to escape. Some had good plans but came up short. These two dug a tunnel from the chemical plant in the lower industrial area out toward the wall. The tunnel was discovered with them in it, and they were recaptured before they made it to freedom.