Clifton was a minor criminal wanted in the Oklahoma Indian Territory for robbery, safecracking, and cattle rustling before joining the Doolin Gang in 1892. Upon joining the gang, Clifton took part in the remainder of the Doolin Gang's bank robberies including the 1893 gunfight with law enforcement at Ingalls, Oklahoma where three of his fingers were shot off. Following the gang's escape, and eventual disbandment, a bounty of $3,500 was placed on Clifton becoming popularly known as the "most killed outlaw in America", as people would repeatedly turn in a corpse claiming the body as Clifton despite the fact the bodies had all ten fingers while others, who would randomly cut off three fingers, would often cut the wrong ones. Clifton was reportedly killed near Blackwell, Oklahoma by Deputy US Marshal Chris Madsen in 1896. While the man in question was missing the correct fingers, it was suspected the outlaw killed may have actually been Buck McGregg. However, that is unlikely as Clifton never surfaced again, and Madsen was said to have known Clifton.
The actor Buck Taylor was cast as Clifton under the nickname "Dynamite Dick", instead of "Dynamite Dan", in the 1981 film, Cattle Annie and Little Britches, a fictional portrayal of teenaged Oklahoma bandits.
- Sifakis, Carl. Encyclopedia of American Crime, New York, Facts On File Inc., 1982
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