Pretty Boy Floyd was an American bank robber and outlaw who went by a number of aliases: Charles Arthur Smith, Frank Mitchell, Pretty Boy Smith, and Choc Floyd. He became legendary for his numerous bank heists, murders, and his ability to escape capture. He is best known for his alleged involvement in the Kansas City Massacre of 1933. Floyd’s outgoing personality, good looks, and the reckless style with which he executed these crimes make him an enduringly appealing figure in American history and legend.
Immortalized in at least seven films, Floyd was also the inspiration for the character Flattop Jones in the Dick Tracy comic strip. A common legend is that Floyd destroyed the mortgage records of poor farmers in the process of his robberies, a gesture immortalized in the popular folk song by Woody Guthrie (1912–1967), “The Ballad of Pretty Boy Floyd,” written in 1939. Guthrie also mentioned the intriguing idea that Floyd may have given lavish gifts to those who helped him: “Others tell you ’bout a stranger / That come to beg a meal, / Underneath his napkin / Left a thousand-dollar bill.” Guthrie’s song both solidified and perpetuated the myth of Floyd as a Robin Hood figure. It is obvious from such lyrics that Floyd’s reputation at the time was already larger than life. He was one of the most infamous outlaws of the time, on a par with John Dillinger, Babyface Nelson, and Bonnie and Clyde.
A mugshot of gangster Charles “Pretty Boy” Floyd (1904–1934), who was one of the most notorious bank robbers of the Great Depression. Although a ruthless murderer who kept a tally of notches on his pocket-watch as a record of his kills, Floyd also garnered something of a Robin Hood reputation amongst the poor and working class, and was the basis for Flattop Jones in the Dick Tracy comic series. (Bettmann/Corbis)
Much about Floyd’s early life is disputed. Charles Arthur Floyd was born February 3, 1904, in Bartow County, Georgia, to Mamie Helena Echols Floyd and Walter Lee Floyd. The Floyds were a farming family of Welsh descent. The family moved to Sequoyah County, Oklahoma, in 1911 to escape poverty and to achieve better opportunities for their six surviving children. Near Sallisaw, Oklahoma, they became tenant farmers, but life did not get appear to get much easier for the growing Floyd family.
Floyd was in his twenties, living in Oklahoma’s Dust Bowl, when the Great Depression hit. This nationwide economic crisis, in combination with the environmental catastrophe taking place in the Midwestern United States, necessitated a creative approach to making a living. Floyd left home to find work, as did so many other young men of that era. He was employed for a time as a farmhand. However, Floyd soon became involved in bootlegging (the illegal distribution of alcoholic drinks during Prohibition), and this served as his introduction to the criminal underworld. His first arrest was for holding up a post office at the age of eighteen.
He returned to Oklahoma and married Ruby Hardgraves in 1924, and they had a son, Jack Dempsey Floyd (after the champion boxer, Jack Dempsey). Floyd soon left town, however, buying a gun and hitching a ride in an empty train car with a friend. Floyd held up a Kroger grocery store in St. Louis, for which he spent three years of a five-year sentence in jail; this period of incarceration cost him his marriage and the custody of his young son.
The cultural climate of the Depression undoubtedly helped catapult Floyd and other outlaws to legendary status, when they otherwise might have been maligned as lowlife criminals. There was, in those times, a sentiment that such men and women were victims of hard times, and this romantic notion, combined with the idea that the banks they robbed symbolized corrupt wealth, elevated outlaws to the status of folk heroes.
Floyd was suspected of being involved in the Kansas City Massacre of June 17, 1933, in which four law enforcement officers were killed in a shootout trying to prevent the escape of a prisoner, Frank “Jelly” Nash. A manhunt for Floyd was set into motion by this event. To this day, it is unclear whether he participated in this notorious shooting, although Floyd himself denied it and most evidence points against his involvement. He didn’t hesitate to confess to other crimes. Floyd kept a tally of everyone he killed by filing a notch on his pocket-watch for each. Ten notches were found on the watch after his death.
Depression-era criminals were the first generation of outlaws to travel far by car; the transitory nature of such gangsters and bank robbers in general—and of Pretty Boy Floyd in particular—can be credited to some extent as having facilitated the rise to power of the Federal Bureau of Investigation, the resources of which came to far outstrip the paltry abilities of state and local law enforcement.
Dick Tracy
Born in Prohibition-era Chicago, Dick Tracy provided a gangland-themed police detective protagonist, which offered readers a gritty, noir-flavored contrast to classic comic book superheroes. The title character, Dick Tracy, was a sort of Eliot Ness of the comics pages, square-jawed and square-dealing, fighting crime and corruption with an All-American, straight-arrow sensibility. The villains who found themselves outmatched by Tracy included Flattop, Pruneface, and Putty Puss, cartoon stand-ins for a real “Most Wanted List” of notable gangsters such as Al Capone, John Dillinger, and Pretty Boy Floyd. Dick Tracy was born in the pages of the Chicago Tribune in 1931, drawn by cartoonist Chester Gould, who continued to be the hand that gave Tracy life until 1977. Notable for its use of bright colors, sharp outlines, and realistic depiction of police procedure, Dick Tracy provided a template that continues to be popular to this day.
C. Fee
Floyd achieved notoriety in his own lifetime because he evaded capture and at one point staged a dramatic escape. Following his arrest and conviction in December 1930 for bank robbery, Floyd escaped by jumping out of the window of the moving train that was carrying him to the penitentiary. It took four years before the law caught up with him again. A major factor in the success of Floyd’s heists and his evasion of law enforcement, and a testament to his nationwide fame even during his lifetime, was the amount of support he received from family, friends, and strangers across the country.
J. Edgar Hoover (1895–1972) dubbed Floyd “Public Enemy Number One” in July 1934, following the death of John Dillinger, who previously held that dubious title. Floyd eluded capture until October 22, 1934, when he was shot multiple times in a standoff against local police and FBI officials in a cornfield near East Liverpool, Ohio. His funeral was held in Oklahoma, and more than 20,000 people are said to have attended.
Robin Potter
See also Bass, Sam; Boles, Charles E. “Black Bart”; Bonney, William “Billy the Kid”; Bonnie and Clyde; Capone, Alphonse “Scarface”; Dillinger, John; James, Jesse; Outlaw Heroes
Further Reading
Bruns, Roger. 1995. The Bandit Kings: From Jesse James to Pretty Boy Floyd. New York: Crown.
Coombs, Karen Mueller. 2002. Woody Guthrie: America’s Folksinger. Minneapolis: Carolrhoda Books.
Hamilton, Sue L. 1989. Public Enemy Number One: Pretty Boy Floyd. Minneapolis, MN: Abdo.
King, Jeffery S. 1999. Life and Death of Pretty Boy Floyd. Kent, OH: Kent State University Press.
Wallis, Michael. 2001. Pretty Boy: The Life and Times of Charles Arthur Floyd. New York: W. W. Norton.