Lawmen & Outlaws
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William "Bill" Doolin

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Bill Doolin Does It
Outlaws Capture the Federal Jail
Submitted by: Bob Chada

The Guthrie Daily Leader, July 7, 1896
Fourteen make their escape - Guards overpowered and made to face death - One prisoner Comes back - One brave trusty knocked in the head - Takes his wife along - Doolin and Dynamite Dick hold up a young man and woman whe are compelled to walk home - No trace of the gang - Oklahoma has had another jail break, this time of mammoth oroportions ad thirteen desperate criminals whose capture has cost the government thousands upon thousands of dollars, are again at large and ready to prey upon the people. At 9 o'clock Sunday night while the city was shrouded in darkness and the people were at church or sitting quietly at home, the prisoners at the federal jail led by Bill Doolin, the noted outsaw, made a dash for liberty, overpowered the guards and a portion of them fled into the night and are still at large.
The Flown Birds - The prisoners who escaped are as follows: Bill Doolin, noted outlaw held for murder in the Ingalls fight; Dynamite Dick, alias Dan Clifton, an all around outlaw and slayer of eight men, held for murder in the Ingalls fight; Walter McLain, sentenced from Pawnee for six months for larceny and 90 days for whisky peddling; Kid Phillips, outlaw and all-round tough, sent from Pawnee for one year for larceny. Formerly lived n Norwich, Kan. E. V. Nix, charged with purgery in the Oklahoma City land office and held for forfeiture of bond. Charles Montgonery, sent for ten months for larceny. Lee Killman, sent from Pawnee for six months for whisky peddling. W. H. Jones, of Pottawatomie county, charged with counterfeiting. Henry Irwin, sent from Woods county one year for postoffice robbery. William Crittenden, sent from Pawnee one year for larceny. James F. Bloack, under incictment for perjury at Oklahoma City. C. E. Lawrence, charged with robbing a postoffice in Kingfisher county. George Lane, charged with peddling whisky in the Osage country. These are the thirteen still at large.
Wm O Beck, charged with selling shisky in the Osage country, went with the gang out of jail and accompanied them half a mile up the railroad track but by that time considered better and returned and again asked to be admitted to the jail.
How It Was Done - From the stories of the guards upon duty at the jail and the prisoners who did not escape even though they had the opportunity, the manner n which the dash was made and carried out to successful fruition was learned - and the whole account will be fore easily understood if the plat of the jail given above is studied for a short time.
The more despirate prisoners are kept at all times in the large steel cell near the center of the building. The door of this cell opens upon the corrider which runs across the fromt of the jail and has two combination locks, one in a large steel box at each side of the door.
Back of this steel cell and running up to the front corrider at either side of it is a large corridor called the "bull pen" in which the majority of the prisoners are allowed to run at large in the day time, while about its sides run a tier of cells in which they are locked at night. Bill Doolin had been kept locked in the steel cell right along until a short time ago, when he became sick and had a number of fits, which were feigned. On account of this supposed sickness he was allowed the liberty of the bull pen at day and locked in the cell at night.
It is customaty to lock the prisoners in their cells between half past eight and nine o'clock each night, J. S. Miller, one night guard, doing the locking up and J. T. Tull, the other night guard, the unlocking in the morning.
At 8:45 Sunday night the men started to do the locking up, everything appearing to be as unual and the prisoners all ready to go to bed. Miller tood off his rebolver and placed it in a box at one side of the front door, it being dangerous to go in among the crowd of prisoners with a revolver. With keys in hadhe was then let thrugh the "bull pen" door and started back toward the row of cells at the reat. The trusty who usually accompanied him, carrying a candle, was half a minute late in getting his candle lit, and Miller was well to the rear of the jail when the trusty came through the door. This seemed to be just the opportunity the more desperate of the prisoners had been waiting for. At the right of the door in the corner of the outer corridor sat a bucket of water so the prisoners could reach through the bars and get a drink of water, and they were in the habit of filling tin cans with water to take to their cells at night, so when Guard Tull saw the negro prisoner, George Lane standing in the corner of the "bull pen" reaching through to the water bucket, he thought nothing of it. As the trusty passed through the door with the candle, the negro mumbled something about not being able to reach his water can and reached his arrn through the door and around the water bucket. For just an instant Tull let his eyes fall toward the water bucket when the negro pushed his head and his shoulders through the doorway, gave a termendous shove, and quicker than a flash, had his arms around Tull holding him in a vice-like grip with his arms pinned tight, while McLain, Kilian, and the counterfeiter, Jones, all three rushed upon him and Killian tore his revolver from the holster under his arm. It was done in five seconds and before Miller culd run half the length of the bull pen Doolin went through the door, shutting and locking it, leaving Miller and the trusty helpless and unarmed among the prisoners.
Tull was dragged to the middle of the corridor, in front of the steel cell door, and ordered to open the combination, while McLain pointed a revolver at this temple and Jones stood in fromt of him with an upraised hatchet he had secured from a table in the corridor.
No Interfearence Allowed - Bill Dean, a trusty, who was sitting at a desk in the corridor, ran toTull's assistance, bet he was knocked down with the butt of a revolver, kicked, and dragged and compelled to go down the stairway into the basement. Jim Beef, a Creek Indian charged with cattle theft, was also in the corridor and attempted to get to the box containing Millers gon, but Doolin beat him, grabbed the weapon and drove him into the basement also. Doolin now held the gun against Tull's breast and ordered him to open the combination or die, but he still refused. Tired of parleying with Tull, they opened the door and threw him nto the bull pen and dragged Miller out and stood him up against the large front door and ordered him to open the combination.
Facing Death - With the revolver pushed in his face and another in his stomach and a hatchet constantly brandished over his head, Miller stood and parleyed with them for nearly ten minutes, until Doolin becoming apprehensive of the fleeting time, told him that if the combination was not opened in one minute, they would kill him. Seeing in the eye of the noted outlaw before whose weapons so many had fallen and seeing that he meant what he said, Miller felt that it was no longer safe to parly and stepped up to open the combination. These five men were virtually free for there was nothing to hinder them stepping through the great front door and escaping, but they desired also to free their friends in the steel cage and for this they parleyed and wasted precious time.
Freeing their Friends - Had they been thwarted in this they would undoubtedly have killed the guards out of revenge and then escape without their companions. When Miller got the first combination worked they pushed him aside and opening the box took there from a six-shooter belonging to Kuykendal, one of the day guards, and then ordered Miller to open the other box. When this was done they opened the cell door and invited the prisoners to come out and join them. But nine of the sixteen in the cell complied, the others prefering to remain and Miller was then pushed into the cell and the combination locked.
The Flight - Jones and Killian then went back into the bull pen and took the large front door key from Tull and invited the thirty-five prisoners still in there to come out and go with them, but all refused to go and the pen door was then locked. Jones unlocked the front door and the fourteen men ran hurriedly down the front steps and out into the dark. Everything was propitious for them, the night dark, no electric lights burning and nobody on the streets, and their flight down the streets was unnoticed.
The Alarm - As soon as they were gone Miller, who was locked securely in a cell, began to call for help in tones that could be heard six squares away. Bob Shugart, one of the prisoners who had gone into the outer corridor but refused to escape with the srowd, went to the telephone and gave the alarm. The escaping prisoners, before going, had torn the telephone wires from the wall but did not succeed in breaking the connection, and soon the alarm was given generally.
A crowd doon gathered at the jail, but it was some little time before Jim Montgomery, one of the day guards, arrived and opened the combination to let Miller out of the cell and also release Tull from the "bull pen." It was a lucky thing for Montgomery that he was not present when the prisoners made their dash for liberty, for they told the others before going that they would kill "Mont" if they could find him.
Got Tired - A majority of the prisoners ran north on Second street to the railway and took the track out of town. After running about half a mile, Doolin fell exhausted and the whole crowd laid down beside the track and rested. When they started on Wm. Beck remained quiet and soon returned to the jail telling which direction the balance had taken. Doolin seemed completely exhausted from the excitement and effort of getting away. He, with the negro Lane, counterfeiter Jones, McLain and Killian with Dynamite Dick and one or two others had evidently planned the work and were waiting a favorable opportunity to carry it out, the other prisoners knowing nothing of it.
The Real Outlaw - When Doolin go outside the bars and got hold of a revolver all his look of mildness suddenly disappeared and he became a very demon. His eyes shown with the light of hell, his hair fairly bristled all over his head, and with set teeth and a grin of horror he shoved his revolver now in the guard's face, now in his stomach, now in his side, with his finger clutching at the trigger, seeming to need only the beginning of slaughter to complete his demoniacal joy. He was thirsty for blood and anxious for an excuse to shed it. His whole action showed that he had long waited for that moment - waited and schemed and planned for it - his long shamming illness, his withdrawing money from a Guthrie band and the recent disappearance of his wife from her home being but incidents of the preparation. In light of his actions here how flat falls all the twaddle he talked last summer about being glad he was caught and have a fair trial and the rot about his giving himself up to Bill Tilghman. Tilghman, by the way, after risking his life so often and working so hard to capture him by this escape of Doolin loses all the compensation for his artuous labors for the rewards were all for arrest and conviction, and he has never been convicted and from present indications never will be.
Before leaving the jail the gang took from the combination boxes money belonging to the jailer and guards, a half dozen coats, vests and hats from the wall, a sack of peaches and numerous other articles, and as they fled out Doolin had Miller's revolver, McLain had Kuykendall's, and Killian, Tull's, while the Negro Lane had a long iron bar and Jones a hatchet.
Took His Wife - Walter McLain, one of the ringleaders, with revolver in hand went down Noble avenue and across into West Guthrie to the home of Deputy Marshal Joe Reynolds, where is wife was bording. She had retired for the night but he routed her out, telling her to hurry as hehad horses waiting. In night clothesand barefooted she came, carrying a dress and shoes, and they hurried off on foot. Just west of town they attempted to stop a man driving toward town, but the horse took fright at the woman in white and dashed past. It is reported that they succeeded in getting a conveyance further out and went on west.
A Startled Couple - A little before 10 o'clock W. A. Koons, a clerk in the county treasurer's office, and Miss Winnie Warner, a young lady school teacher, were driving along a mile north of town., Mr. Koons bringing the young lady in from her home in the country to ger grandfather's, Rev J. N. Shepherd, where she was to remain several weeks and attend Normal. They had been talking a ways back about the darkness and what a good night it was for a hold-up, but were getting close to town and no longer apprehensive when a man stepped alongside the buggy and poking a revolver into Mr Koon's ribs ordered him to stop. He has but one arm and could do nothing toward defense, and when two others stepped up on the other side, one with upraised hatchet, the young people got out of the buggy with alacrity. Miss Warner attempted to hide her gold watch, but the men said they wanted nothing but the horse and buggy, and even handed out the lap rope, but Koons said he didn't want to keep it and threw it back in the buggy. The three men got in the buggy, turned the horse toward the north and sped away in the dark, turning east at the first cross roads and heading, no doubt, for Cowboy Flats, where they will find friends and good hiding places.
The Chase Begins - As soon as the alarm was given Chief Deputy Kane sent telegrams to all points telling of the break, and deputies at several points were ordered out. Deputy Colcord, ar Perry, started in the night for the "Flat Iron" country and others left here for Stillwater. Deputies also left here for the Cowboy Flats and the Cimarron country east of Perkins, but up to a late hour last night no definite trace of any of the missing men had been found.

See map of the jail


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Updated: Wednesday, 06-Aug-2008 06:46:45 CDT

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