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Most Killed Outlaw in America

Updated on August 19, 2015

Dan Clifton, better known as “Dynamite Dan,” was a member of the notorious Doolin-Dalton gang that operated primarily in the Oklahoma Territory. He took part in numerous robberies committed by the outlaw gang during the 1890s. The place and date of his birth is unknown.

Dynamite Dan joined the “Wild Bunch” around 1892, the same time as 3 others: “Tulsa Jack,” Red Buck Weightman and William "Bill" Dalton, brother of the infamous Dalton Boys. It’s known, before he joined the Doolin-Dalton gang he was wanted in the Oklahoma Indian Territory for numerous offenses. His specialties were robbery, safecracking and cattle rustling.

As with other colorful Old West characters having a descriptive nickname there are several stories of how he came by his odd moniker. But, the true documented account says Clifton lost 3 fingers in a shootout with the law during a bank robbery in 1893 at Ingalls, Oklahoma.

He became known as the "most killed outlaw in America" after a $3,500 reward was posted for his capture dead or alive. Seeing as he was missing 3 fingers, bounty hunters were continually trying to collect the reward by producing a body from which they had removed 3 fingers. The problem was they were always the wrong 3. Besides, Dynamite Dan had fled to Arizona where he was wanted for murdering two Mexican ranchers.

In September of 1893, a posse numbering about 30 headed towards Ingalls, Oklahoma, where they were believed to be holed up at a hideout they had there. The confrontation would later become known as the Battle of Ingalls. Three deputy marshals and two innocent bystanders were killed when the 2 factions collided.

The outlaws fared better sustaining only 3 wounded members: "Bittercreek" Newcomb, Charley Pierce, and "Dynamite Dan." Only one gang member, "Arkansas Tom" Jones, was captured. He was later sentenced to fifty years in prison.

Clifton was eventually captured by a posse of deputies out of Paris, Texas on a whiskey charge and returned to Oklahoma. He and Doolin were held at the jail in Guthrie. But the pair managed to free themselves during a mass jail break along with about a dozen other prisoners when a guard was overpowered. Meanwhile authorities were slowly, but methodically eliminating the rest of the gang. Marshal Bill Tilghman captured “Little Bill” Raidler in 1895 and Red Buck Weightman was shot and killed by a posse at Eureka Springs, Kansas.

The gang pulled its last job April 3, 1895. They held up a train at Dover in Oklahoma Territory. After the robbery, unaware there was a posse closing in on them, they made camp near Ames. When the deputies rushed the camp, “Tulsa Jack” was shot and killed. Although the rest of the gang escaped they would never again be reunited as a gang.

The next month, while hiding out at a place called the Dunn farm, Bitter Creek Newcomb and Charlie Pierce were shot while they lay asleep by their hosts Bill, John and Dal Dunn. They took the bodies to Guthrie to collect a $5,000 reward.

On Aug. 24, 1896 Bill Doolin was ambushed and killed by Deputy Marshal Heck Thomas's posse. Now, all that remained of the Wild Bunch were Dynamite Dan and “Little Dick” West. They rode with the Jennings Gang for a short time. After leaving that gang they were systematically tracked down and killed by the law.

One account says Dynamite Dan was killed by deputies on Nov. 7, 1896 near Checotah, in Indian Territory. Another says he was shot and killed by deputies as he tried to escape from a farmhouse outside of Newkirk, Oklahoma on December 4, 1896. Clifton was buried in the town cemetery at Muskogee, Oklahoma.


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    • JY3502 profile image

      John Young 6 years ago from Florence, South Carolina

      Daffy, well I saw it first and the guy was trying to take it away from me!!

    • Daffy Duck profile image

      Daffy Duck 6 years ago from Cornelius, Oregon

      Cutting off fingers to collect a reward. This just shows how depraved people were back then.....about as much as some are today. Faking injuries to collect disability, fighting at a store over an item during the holiday season. It seems that people find new ways to reach new lows. "How low can you go" should only apply to the limbo.

      Enjoyed the story. :)

    • Paradise7 profile image

      Paradise7 6 years ago from Upstate New York

      The west really was wild back then, and lawless. It's hard to realize now how very rough people were. Great story. I liked the fingers, also.

    • JY3502 profile image

      John Young 6 years ago from Florence, South Carolina

      Hey Western, you might say he gave them a finger or two.

    • WesternHistory profile image

      WesternHistory 6 years ago from California

      Very interesting hub. Great story about the bounty hunters and the missing three fingers. Whenever I've researched characters from the old west days I find stories that are almost too wild to make up. It's amazing how many gangs were roaming the old west but then again I think that law enforcement back then was spread a bit thin.