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A note from Curly - A correction was made to this page 5/20/01 thanks to the help of
Roger Myers of Cockeyed Frank's Old West History Page

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William M. "Bill" Doolin
- 1858-1896
    The son of an Arkansas farmer, Bill Doolin rode into the Oklahoma territory in 1881.  He found work at the H-X Bar ranch as a cowboy, which was where the Dalton Brothers occasionally worked.  Doolin was a skilled cowboy and was equally skilled with his six-shooter.  He was involved in a shooting in Coffeyville, KS. in 1891, he then left the ranch.  Two deputies were trying to break up a beer party, they started to pour the beer on the floor, when several cowboys, including Doolin, pulled their guns and shot the deputies to death.  Doolin fled and joined the Daltons.  That's when things turned for Doolin and he participated in many bank and train robberies with the Daltons.

    As luck would have it, Doolin's horse pulled up lame right before the fateful Coffeyville raid of Ocotober 5, 1892.  He told Bob Dalton that he would go to a nearby ranch and get another mount and then join up with the gang later.  As Doolin arrived at the Coffeyville city limits, Bob & Grat Dalton, Bill Powers and Dick Broadwell were already dead, dying at the hands of angry citizens in a hail of gunfire. There is another story though, about how Doolin missed the Coffeyville raid.  Doolin quit the gang after arguing with Bob Dalton over how the money from the raid would be divided.  Either way, it was Bill Doolin's lucky day.

    Ironically, in 1893, Doolin married a preacher's daughter and subsequently organized one of the most notorious group of outlaws in Oklahoma, Doolin's "Oklahombres".  In the gang were Bill Dalton, one of the remaining Dalton brothers, George "Bitter Creek" Newcomb, Little Dick West, Dan "Dynamite Dick" Clifton, George "Red Buck" Weightman, Roy Daugherty, also know as Arkansas Tom Jones, Charley Pierce, Alf Sohn, Ole Yantis, Tulsa Jack Blake, Bob Grounds, and Little Bill Raidler.  For three wild years, the gang robbed trains, banks and stagecoaches and had their headquarters in the town of Ingalls, OK.

    On the afternoon of May 30, 1893, Doolin and three of his gang robbed a train near Cimarron, KS.  As the gang was fleeing, they ran into a group of scouts from Fort Supply on or near the Fred Taintor ranch SE of present day Englewood, KS., a gunfight ensued and Doolin was shot in the right foot.  The gang managed to escape at nightfall.  On September 1, 1893, a small army of lawmen slipped quietly into the outlaw town of Ingalls.  Inside of the Ransom & Murray Saloon, Doolin, Dalton, Weightman, Clifton, Blake and Newcomb were drinking heavily, Roy Daugherty went up to his room on the second floor.  As the gang prepared for a little poker, Newcomb went outside to check on the horses.  Dick Speed, a deputy who had taken cover across the street of the saloon, immediately fired upon Newcomb, beginning the Battle of Ingalls.  Newcomb sounded the alarm and then mounted his horse and rode out of town in a hail of gunfire.  The outlaws inside the saloon and Daugherty from his second floor room were firing wildly from the windows at the posse.

    As Deputy Speed ran down the street, he was fatally shot by one fo the gang members.  The shooting was so wild that it killed a boy watching the fight, Del Simmons and struck another innocent citizen in the chest.  For a few minutes, the guns fell silent.  The deputies called out to Doolin to surrender, and Doolin yelled his answer: "You go to hell!"  The firing commenced again.  Doolin and the gang then made a run for the livery stable and mounted their horses, firing wildly at the lawmen and the lawmen firing back as the gang rode in the same direction Newcomb went.  Bill Dalton lost his horse and was trapped behind a fence.  Deputy Lafe Shadley ran to Dalton to kill him with a shotgun, but Dalton quickly turned and killed Shadley instantly.  Just then, Doolin reappeared, riding towards Dalton.  Dalton climbed on the back of Doolin's horse and they raced out of town.

    Doolin and the gang continued their robbing, their largest take being around $40,000.00 for an East Texas bank.  The gangs days were numbered as more and more lawmen were on their trail.  Chris Madsen, Heck Thomas and Bill Tilghman, the best lawmen of the time, were on the heels of Doolin and the gang and never gave them a rest, chasing them through five states.  Outlaw or not, Doolin was considered a fair man.  There is a story that Doolin actually saved the life of Bill Tilghman by preventing Red Buck Weightman from shooting Tilghman in an ambush.  Tilghman was know for his honesty and fairness, using force only when necessary and had the respect of both lawmen and outlaws.  As Tilghman's posse was closing in on Doolin one morning, Doolin and the gang were eating a hearty breakfast at a farmhouse, the farmer believing Doolin and the boys were posse members.  Doolin stepped outside the farmhouse and spotted Tilghman and his posse approaching from a distance.  Doolin then told the farmer that another posse would be showing up soon and they would be hungry too and would want breakfast and that they would pay for all of the meals, including Doolin's boys'.  Tilghman and the posse arrived and ate a large breakfast.  The farmer then told Tilghman that "the other boys" said he would be paying for there meals too.  Tilghman the reluctantly paid for not only his posse's meal, but for Doolin's meals as well.

    On May 20, 1895 in Southwest City, MO., the Doolin gang robbed a local bank.  By chance, J.C. Seaborn, the state auditor was there, seized a gun and tried to stop the gang from robbing the bank.  Seaborn ended up dead and Doolin had a severe wound to the head.  A few weeks later, near Dover, OK., while camping near the Cimarron river, lawmen rode in on them.  On guard was Tulsa Jack Blake, who warned the gang and exchanged shots with the advancing posse.  Black was shot and killed as Doolin and the rest of the gang escaped. The numbers in Doolin's gang were dwindling, most of the members riding off to seal their own bloody fate.  Doolin was in Eureka Springs, OK., when the relentless Bill Tilghman tracked him down.  In a bathhouse, the two men fought with fists until the strong armed Tilghman knocked Doolin out and arrested him.  Tilghman then brought his prisoner to Guthrie, OK. to stand trial for bank and train robbery.  Thousands of residents lined the streets as they rode into town to catch a glimpse of the famous outlaw.  Doolin was cheered as he was taken to jail and vowed that he would never go to prison.  A few weeks later, Doolin engineered a mass jail break, he and 37 other prisoners escaped.

    Doolin then rode to Mexico and hid out at the ranch of writer Eugene Manlove Rhodes, but he missed his wife and child and was bound and determined to have them with him.  He then rode back to  his family in Lawton, OK.  On the night of August 25, 1896, Doolin was riding to his father-in-law's farmhouse, where his wife and child were staying.  A posse, led by Heck Thomas, heard that Doolin was in the area so they were waiting for him.  Doolin came up, on foot leading his horse and carrying his rifle, whistling as he walked in the moonlit night.  The Thomas shouted from behind some bushes, calling Doolin to surrender.  Doolin raised his rifle, which was quickly shot out of his hands by the posse.  He then pulled his six-gun and fired twice before being killed instantly by a blast from Deputy Bill Dunn's shotgun and rifle fire from Thomas.  As was customary of those days, Doolin's dead body was displayed, with his shirt off, to show his fatal wounds.
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