He may have been one of America’s best-loved outlaw: tens of thousands of people paid their respects at Charles “Pretty Boy” Floyd’s funeral after he was shot down by the FBI on Oct. 22, in 1934 in East Liverpool, Ohio.
The FBI agents, however, were not among the mourners. Earlier that year, Floyd has been declared Public Enemy No. 1 by the agency for his alleged role in the 1933 Kansas City Massacre, when machine-gunners killed three policemen and one FBI agent as they attempted to return escaped criminal Frank Nash to prison. Floyd was named as one of the shooters. In a story published the day of his death, TIME described Floyd as “a murderously cool shot, trigger finger has already accounted for at least six deaths.” Summarizing his criminal CV, the story went on:
At 18 he robbed a neighborhood post-office of $350 in pennies. A three-year apprenticeship in the St. Louis underworld landed him, in 1925, in Missouri Penitentiary for a payroll robbery. There he peddled drugs, struck down guards, and met “Red” Lovett, who teamed up with him on his release in 1929. For the next four years he robbed rural banks, taking on new partners as his old ones fell dead by the wayside.
The Oklahoman public remembered him differently: he was their Robin Hood. Rumors circulated that he had destroyed mortgage papers on heists, freeing hundreds of struggling farmers from foreclosure.
It was said that Floyd was paying to feed a dozen families who might have otherwise gone hungry. His reputation for generosity to the “hill people” was repaid in kind when they helped him hide from the law in the foothills of the Ozarks.
He couldn’t hide in the hills forever, though. After he crashed his getaway car into a telephone pole, the FBI chased him down in a cornfield and fired on him while he ran. But his story didn’t end there; five years after his death, Woody Guthrie memorialized him in in the song “Pretty Boy Floyd,” with the lyrics:
But many a starvin’ farmer The same old story told How the outlaw paid their mortgage And saved their little homes…
Yes, as through this world I’ve wandered I’ve seen lots of funny men; Some will rob you with a six-gun, And some with a fountain pen.