The Mammoth Book of Prison Breaks

by Paul Simpson

  In the version Whitehill passed on down through his family, Billy used the freedom he had been granted to reach a chimney. An accomplice on the outside had lowered a rope down inside the building, and the Kid was able to use this to get out. However, when he was interviewed by the Silver City Enterprise in 1902, Whitehill claimed that he arranged for Billy to be freed from his cell, but mistakenly, the future outlaw was left unsupervised. When Whitehill realized that there was no sign of the Kid, he raced outside the jail in search of him. A Mexican loitering nearby told him that a young man had come out of the chimney. Whitehill ran back inside the jail, and looked up the big old-fashioned chimney. Clearly visible were handmarks where the fugitive had clawed into the thick layer of soot which lined the chimney. Even though the chimney was only as wide as a man’s arm, the Kid had been able to squeeze his way through.

  As Whitehill said to the Silver City Enterprise reporter, it was shortly after this that Billy the Kid “commenced his career of lawlessness in earnest”. He moved to Arizona, and after an argument got out of hand, he killed Frank “Windy” Cahill in what was described as a criminal and unjustifiable shooting in 1877. He then became part of a feud between cattlemen and merchants in the New Mexico area of Lincoln County. The Kid worked for English cattle rancher John H. Tunstall, who, together with Scottish lawyer Alexander McSween, were arguing with Lincoln merchants James Dolan and Lawrence Murphy. Tunstall was murdered in January 1878 by men working for Dolan and Murphy; the Kid and others in Tunstall’s employ swore revenge. Calling themselves “Regulators” they engaged in a vicious battle with Dolan and Murphy’s workers. After they killed two of their enemies in March 1878, they were declared outlaws.

  Sheriff William Brady and Deputy George Hindman were both killed when they tried to ambush McSween, and a bounty hunter also fell to the Regulators. In July, matters came to a head with the Regulators trapped inside McSween’s house for four days. Even the army was unable to dislodge them, but when the house was set on fire, the Regulators ran for their lives. The Kid managed to survive; most of the others were shot as they fled. He and the few other remaining Regulators were outlawed for good.

  Pat Garrett was elected as Sheriff of Lincoln County in November 1880 after promising to restore law and order to the area in the aftermath of the bitter feud. On 23 December, he captured Billy the Kid at Stinking Springs, four days after he and his posse ambushed the remnants of the Regulators at Fort Sumner. They were taken to Las Vegas, and then to Santa Fe, where they were held in the prison for the first couple of months of 1881. The Kid had no intention of remaining a prisoner, and started digging a tunnel, which was betrayed to the prison authorities on 28 February. As a result, he was placed in solitary confinement, and shackled to the floor of his cell by the local sheriff.

  After an attempt to try him in the federal court for the murder of the bounty hunter, Buckshot Roberts, which failed when Billy’s lawyer pointed out to the court that the location of Robert’s death wasn’t federal land, the Kid was handed back to the territorial authorities (New Mexico didn’t become a state of the union until 1912). He was charged with the murder of Sheriff Brady, and after a one-day trial, was found guilty. On 13 April 1881, Billy the Kid was sentenced to be hanged exactly one month later, on Friday 13 May, in the town of Lincoln.

  It took five days for Billy to be transported from Santa Fe to Lincoln, and his guards expected him either to attempt to get away, or his friends to try to rescue him. It was made abundantly clear to him that the first bullets fired would be at him, not his rescuers. In the event, the journey was uneventful, although the Kid was regularly taunted by one of the guards, Bob Olinger.

  On 21 April, the Kid was escorted into his new home in the new Lincoln County courthouse, which had previously been the store run by his enemies, Murphy and Dolan. His guards were Olinger and Deputy James W. Bell, who were warned by Sheriff Garrett to watch their prisoner at all times, even though he was often chained to the floor of what had been Murphy’s bedroom.

  A week later, Garrett was away from Lincoln collecting taxes (or possibly collecting timber to use for the Kid’s gallows). He had reinforced the instructions to Olinger and Bell, knowing that Billy would now be desperate to find a way to escape his fate. Olinger continued to taunt the Kid: the two loathed each other, because they had been responsible for the death of one of the other’s friends. Some reports even suggest that Olinger had drawn a line across the room, and warned Billy that if he crossed it, he would be summarily executed. Certainly, a contemporary witness described Olinger as “a big burly fellow, and every one that I ever heard speak of him said he was mean and overbearing, and I know that he tantalized Billy while guarding him, for he invited me to the hanging just a few days before he was killed. Even after he was killed I never heard any one say a single nice thing about him.”

  The Kid didn’t seem to have a problem with Deputy Bell, or even Sheriff Garrett; the latter wrote an account of his dealings with Billy in which he noted that the Kid acknowledged that the sheriff had acted “without malice, and had treated him with marked leniency and kindness”. Those qualities were in short supply soon after 5 p.m. on the afternoon of 28 April.

  There were five other criminals being held at the Lincoln County courthouse that day, and it was Olinger’s duty to take them for something to eat. Billy was therefore left on his own in the jail with Deputy Bell. He asked if he could use the privy, which was in an outhouse behind the prison. Bell agreed, and unshackled him from the floor. Still bound at ankles and wrists, Billy was escorted down the stairs, and out back to the toilet, where he was left to carry out his business unsupervised. Bell then followed Billy back into the courthouse, and up the stairs.

  At the top of the stairs, Billy the Kid turned round and fired a gun point-blank at Bell. The deputy crashed down the stairs, and out of the back door, where he fell into the arms of cook Godfrey Gauss, who lived behind the courthouse. Although Billy almost certainly picked up the weapon in the outhouse, it has never been satisfactorily explained who left it for him. One theory suggests that Tunstall’s clerk, Sam Corbet, had visited Billy every day while he was in the courthouse, and on one occasion was able to slip him a note or otherwise let him know the one key word, “Privy”. That was enough to alert Billy to the presence of something that would help him, smuggled in there by another friend, José Aguayo.

  Sheriff Garrett believed that Billy had somehow got ahead of the deputy, been able to reach the armoury, and used one of the weapons from there to kill Bell. One witness claimed that Billy had told him that he had attacked Bell and used the deputy’s own gun against him. Of course, had ballistics evidence been available, most of these theories would have been discounted immediately.

  In the confusion that followed, Billy was able to slip his wrist-irons off – getting out of such handcuffs had been his party trick for some years, since he had very dainty wrists – and shuffled his way into the armoury, where he was able to collect Olinger’s pride and joy, a brand new 10-gauge Whitney shotgun. He moved to the window.

  Olinger had heard the shots, and probably initially thought that Bell had been forced to shoot their prisoner. As he entered the yard, he heard a shout from Gauss telling him that Bell was dead. A moment later, Billy yelled, “Hello Bob . . . Look up, old boy, and see what you get,” from the window. Olinger did as the outlaw suggested, to see his own shotgun pointed directly at him. The Kid remorselessly let him have both barrels. Olinger collapsed to the ground, killed instantly. Billy then destroyed the gun, and threw it down at Olinger’s body.

  As a crowd began to gather, Billy returned to the armoury, and grabbed a Winchester rifle, two pistols and a belt of ammunition. He returned to the window, and told the crowd that he hadn’t wanted to kill Bell: all he wanted was to get away. Gauss, who had been a friend of Billy’s previously, threw him up a pick that he could use to get rid of his leg shackles, then went to find him a horse.

  No one dared take action against Billy as he worked at th
e shackles, finally freeing one leg after an hour’s endeavour. He then mounted the horse (on the second attempt – the first time the horse had bolted, spooked by the dangling iron remaining on Billy’s leg), and rode away.

  The story of Billy’s escape cemented his legend. The Daily New Mexican said that he had shown “a coolness and steadiness of nerve in executing his plan of escape” and that it was “as bold a deed as those versed in the annals of crime can recall. It surpasses anything of which the Kid has been guilty so far that his past offenses lose much of heinousness in comparison with it, and it effectually settles the question whether the Kid is a cowardly cutthroat or a thoroughly reckless and fearless man.”

  The Kid stayed on the run with Garrett on his trail for nearly three months. During the night of 14 July 1881, Pat Garrett shot Billy the Kid at the home of Pete Maxwell in Fort Sumner – possibly in a deliberately set ambush. The headstone on his grave comes from the Warner Bros. film The Outlaw! Because Garrett had shot Billy, he never received the reward for his capture; he lost the next election for sheriff, and his reputation began to dwindle as questions were asked about the manner in which he killed the outlaw. Garrett himself was shot dead aged fifty-seven in 1908.

  Sources:

  El Paso Times, 24 March 1987: “Billy the Kid made 1st escape from Silver City jail”

  Wild West, August 1998: “Billy the Kid: The Great Escape”

  University of Nebraska: Encyclopedia of the Great Plains

  Nolan, Frederick: The West of Billy the Kid (University of Oklahoma, 1998)

  Nolan, Frederick: The Lincoln County War: A Documentary History (Sunstone Press, 2009)

  Boze Bell, Bob: The Illustrated Life and Times of Billy the Kid (Tri-Boze Press, 2nd edition 1996)

  Jacobsen, Joel: Such Men as Billy the Kid: The Lincoln County War Reconsidered (University of Nebraska, 1997)

  Getting Even With the Bankers

  Criminals often have justifications for their crimes, most of which won’t resonate with the ordinary person who isn’t prepared to cross the lines that crooks do to get what they want. But in the 1930s, a gang of robbers almost became heroes to the American public, and when their leader was shot and killed in an ambush by the Bureau of Investigation (the forerunner of the FBI), hundreds came to look at his dead body. The reason: John Dillinger’s gang targeted a specific group of people. As Harry “Pete” Pierpoint explained, they “stole from the bankers who stole from the people”. Some things never change!

  Dillinger’s greatest mistake was giving the Bureau an excuse to come after him. At the time, bank robbery wasn’t a crime with which they became involved in the normal course of events – they might be asked to advise, and assist, but their remit only covered crimes that affected more than one state. During his escape from Crown Point Jail, Dillinger very unwisely travelled across a state line in a stolen car; from that moment on, his fate was sealed.

  John Dillinger was born in 1903, and after getting in trouble with the law for theft of a car, he enlisted in the Navy. The service life wasn’t for him, and he deserted his ship, heading for Indianapolis. He became friends with a pool shark, Ed Singleton, and the pair tried to rob a Mooresville grocer but the amateur robbers were quickly caught. Singleton pleaded not guilty, and received a two-year sentence. Dillinger’s father convinced him to confess and, much to his horror, the young man was sent to Indiana State Prison for assault and battery with intent to rob, and conspiracy to commit a felony, for sentences of two to fourteen years and ten to twenty years respectively. When he was paroled after eight and a half years, he had become an embittered, hardened criminal. As a result of the murders, robberies and other crimes he committed between May 1933 and his death in July 1934, Dillinger was declared Public Enemy Number One.

  Bank robber Harry Pierpoint had met Dillinger when both of them were in the Pendleton Reformatory, and they teamed up again when Dillinger followed Pierpoint to the state prison at Michigan City. Since it seemed likely that Dillinger would be freed soon – many people had complained about the apparent injustice of his sentence, including the grocer he had robbed – he seemed to be the ideal person to work on the outside to help free Pierpoint and his gang of fellow bank robbers, Charles Makley, Russell Clark and John “Red” Hamilton, all of whom were serving between fifteen and twenty-five years for various crimes. If he could find a way of smuggling guns into the prison, then Pierpoint would allow Dillinger to join his gang.

  After Pierpoint’s request for parole was turned down, Dillinger made the necessary arrangements, and ensured that various weapons were transported into the Indiana State Prison within thread boxes. The gang were working within the prison’s shirt factory, and were able to gain access to the boxes. Using the shotguns and rifles, they successfully escaped on 26 September 1933. Two guards were shot during their departure.

  However, Dillinger wasn’t there to greet them. He had been arrested in Lima, Ohio, four days earlier, following bank raids that he had carried out in Bluffton soon after his release in May. When he was searched, the sheriff’s men found papers which seemed to indicate that a prison break was being planned; Dillinger, who could be charm personified when he wanted, persuaded them that they were nothing of the sort.

  Pierpoint’s gang returned the favour on 12 October. Around 6.25 p.m., Pierpoint, Makley and Clark arrived at the Lima jail, claiming that they were from the Indiana State Prison (technically true) and were there to return Dillinger to Michigan City for violating his parole (definitely not true!). Sheriff Jess Sarber didn’t believe them, and asked to see proper identification. Pierpoint didn’t hesitate: he shot Sarber, and then screamed at him to provide the keys to the cells. Sarber refused to answer, so Charles Makley hit him with his gun butt. When Sarber still was uncooperative, his wife, who had been keeping him company in the jail, begged them to stop hurting him, and dug the keys out of a drawer. Pierpoint and his men freed Dillinger and vanished; Sarber died ninety minutes later. “ Get killers. Either dead or alive! Order to Police” screamed the headlines.

  At this point, the Bureau of Investigation became involved in a consultative role, identifying and locating the five men, who didn’t try to stay hidden. They raided various police stations, including one in Warsaw, Indiana, as well as the arsenals at Auburn, Indiana and Peru, Indiana, stealing machine guns, rifles, revolvers, ammunition, and bulletproof vests. They then went on a bank-robbing spree, gaining notoriety. A raid on the First National Bank in East Chicago was a turning point for Dillinger. On 15 January 1934 (the FBI website mistakenly dates this to a month earlier), he shot and killed a policeman, Detective William Patrick O’Malley, while making his getaway. Dillinger denied that he was responsible for the death, but the policeman who he was holding hostage at the time, Hobart Wilgus, was adamant that Dillinger fired the sub-machine-gun burst.

  Dillinger and the gang were apprehended on 23 January, after a fire broke out in the hotel where Russell Clark and Charles Makley were living. The firemen recognized them from the many Wanted posters of Dillinger’s men that were circulating; the local police found three Thompson sub-machine guns, two Winchester rifles mounted as machine guns, five bulletproof vests, and more than $25,000 in cash. Arraigned in a Tucson, Arizona court on 25 January, they were dispersed around the country, with Dillinger sent by plane back to Crown Point, Indiana, on 30 January to stand trial for the murder of O’Malley. (Such air travel was a novelty, and apparently Dillinger complained the whole time.) The others were transferred to Ohio to answer charges of murder for Sheriff Sarber; within weeks, they were tried and convicted.

  Once he had arrived at Lake County jail, Dillinger turned on the charm to the gathered reporters, agreeing to pose for photos with the local sheriff, Lillian Holley, and prosecuting attorney Robert Estill – both would lose their jobs as a direct result of their apparent chumminess with the alleged murderer after his escape. He claimed he was “not a bad fellow, ladies and gentlemen. I was just an unfortunate boy who started wrong,” and answered Sher
iff Holley’s boast that she could keep him with a simple statement that she couldn’t.

  Dillinger appeared before the court on 5 February, and was charged four days later. Although the authorities wanted to move him away from Crown Point, his lawyer, Lou Piquett argued against it. Security measures were kept tight initially – footage can be watched online of hordes of policemen, toting shotguns, keeping guard outside Lake County – but it was gradually relaxed as Dillinger appeared resigned to his fate.

  He was nothing of the sort. Using razor blades, the gangster carved himself a fake Colt .38 revolver out of washboard, with a quarter-inch copper tube inserted to simulate a barrel. (Or possibly, he arranged for a real one to be smuggled in – there is no definitive evidence either way, and three separate “Dillinger guns” can be found on display in museums, each claiming to be the fake that he created!) At 9.15 a.m. on 3 March, nine days before his trial was scheduled to start, Dillinger used the gun to take one of the guards, officer Baker, hostage. He then seized two .45 automatic pistols from a couple of National Guardsmen who had been watching over another prisoner, Herbert Youngblood, as well as a couple of machine guns. He tried to persuade other prisoners to come along, but they refused – only Youngblood was willing to accompany him. Taking deputy sheriff Ernest Blunk with them as a hostage, they exited through a kitchen and a side entrance to the jail. After Youngblood checked for any watchers, Dillinger walked Blunk through to the police garage, and then out into the street. They then went to the Main Street garage, where they took mechanic Edwin Saagar hostage, and proceeded to steal the sheriff’s car! (Dillinger asked Saagar which was the fastest car in the garage, and the mechanic indicated the V8 – it wasn’t a deliberate choice to cock a snook at law enforcement, contrary to the legend.) Blunk was forced to drive the car at gunpoint across country. When Dillinger let his hostages go, he handed Saagar four dollars as recompense. A postal worker who saw Dillinger’s escape called the police, but was told that he must be mad. Only after he insisted did they take him seriously – and discovered the truth.