Charles Arthur 'Pretty Boy' Floyd was a gangster hero in Oklahoma (and, to a lesser degree, the rest of the United States) during the Great Depression. The popular history of Pretty Boy follows the archetype for such folk heroes -- an honest man turns bad after suffering injustice, and is beloved by the common people as he triumphs over the corrupt government. He is finally ambushed after being betrayed by somebody close to him. At this level, the story is similar to that of Billy the Kid, or Robin Hood, or Ned Kelly, the Australian outlaw. As in all of these cases, the real story is more complex and uglier.
Floyd was born in rural Georgia on February 3, 1904. His family moved within a year to Oklahoma, where they worked a farm that never generated much cash. At the age of 17, Floyd married Wilma Hargrove. The popular history says that Floyd committed his first crime when he struck down a sheriff's deputy who had been rude to Wilma, but contemporary sources agree that Floyd simply needed a way to make ends meet.
Time Magazine (22 October 1934) mentions a robbery of a local post-office as his first known crime. At the age of 18 he stole $350 in pennies from them. He was busted for a payroll robbery in St. Louis in 1925 and served three years, When paroled, he vowed that he would never see the inside of another prison. He did not, however, go straight. Partnering with more established criminals in the Kansas City underworld, he committed a series of bank robberies over the next several years; it was during this period that he earned the nickname 'Pretty Boy'. Like his contemporary 'Baby Face' Nelson, Floyd hated his nickname.
Their string of crimes hit a hiccup in Sylvania, Ohio, where they were caught in the midst of a bank robbery and Floyd was sentenced to 15 years. However, he escaped on his way to prison and rebuilt his gang. In the years that followed, he was blamed for a long string of bank robberies. The popular legend holds that he was not, in fact, responsible for all of these, and that his name was being attached to robberies committed by others. In the words of Woody Guthrie, "Every crime in Oklahoma was added to his name." If Floyd found himself presumed responsible for many robberies that were not his doing, this would probably have increased the number of crimes that he did commit. After all, if people are going to presume you guilty no matter what you do, you might as well do the crime. At the same time, it would have increased the number of crimes committed by others, since if you know the police are going to blame somebody else, you might as well do the crime.
Floyd would hide out between crimes in towns near the one in which he had grown up, protected by the locals. The popular legend says that they did this out of love for his generosity and their hatred of the banks, which were at that time foreclosing on many farms. However the contemporary press claimed that he simply bribed them for their silence.
With his partner George Birdwell, Floyd robbed the banks in Earlsboro, Konawa, Maud, Morris, Shamrock, Tahlequah, and on December 12, 1931, two banks in one day at Castle and Paden, Oklahoma. Bank insurance rates doubled, and the governor of Oklahoma placed a $56,000 reward on Floyd's head.
The man was also accused of participating in the Kansas City Massacre, a shootout that resulted in the deaths of four lawmen in 1933. He denied being there, but the authorities and the press were sure he was involved.
After narrowly escaping ambush by the FBI several times, Floyd was finally killed on October 22, 1934 when the FBI agents shot him near East Liverpool, Ohio.
He is remembered today in part because, five years after Floyd's death, Woody Guthrie wrote a ballad romanticizing his life of crime. This song has been performed by many of the great figures in country and folk music, and was recorded by Bob Dylan on the Smithsonian's tribute to Guthrie in 1988. The song plays up Floyd's generosity to the poor, and contains the very famous line
"Some will rob you with a six-gun,
And some with a fountain pen."
Many books have been written about Pretty Boy Floyd, including a semi-fictionalized biography by Pulitzer Prize winner Larry McMurtry and Diana Ossana in 1994.
Sources: TIME,22 October 1934. Also, http://www.geocities.com/Nashville/3448/pretty.html, which in turn relies on the liner notes for Bobby Barnett, 'American Heroes & Western Legends,' Bear Family Records (BCD 16 121 AH), 1997.
The complete lyrics to Guthrie's song appear below.
If you'll gather 'round me, children,
A story I will tell
'Bout Pretty Boy Floyd, an outlaw,
Oklahoma knew him well.
It was in the town of Shawnee,
A Saturday afternoon,
His wife beside him in his wagon
As into town they rode.
There a deputy sheriff approached him
In a manner rather rude,
Vulgar words of anger,
An' his wife she overheard.
Pretty Boy grabbed a log chain,
And the deputy grabbed his gun;
In the fight that followed
He laid that deputy down.
Then he took to the trees and timber
To live a life of shame;
Every crime in Oklahoma
Was added to his name.
But a many a starving farmer
The same old story told
How the outlaw paid their mortgage
And saved their little homes.
Others tell you 'bout a stranger
That come to beg a meal,
Underneath his napkin
Left a thousand dollar bill.
It was in Oklahoma City,
It was on a Christmas Day,
There was a whole car load of groceries
Come with a note to say:
Well, you say that I'm an outlaw,
You say that I'm a thief.
Here's a Christmas dinner
For the families on relief.
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.
And as through your life you travel,
Yes, as through your life you roam,
You won't never see an outlaw
Drive a family from their home.