Pretty Boy Floyd: The Folk Outlaw of the Great Depression

Oct 22, 2025

16 min read

Updated: 15 hours ago

Black-and-white portrait of Charles "Pretty Boy" Floyd over a vintage criminal record, with the title Pretty Boy Floyd: the folk outlaw of the Great Depression

On the afternoon of 22 October 1934, a man in a navy suit knocked on a farmhouse door on Sprucevale Road outside Clarkson, Ohio. He told the widow who answered, Ellen Conkle, that he'd been out hunting and got lost. Could he get a ride to the bus line? She cooked him a meal, he paid her a dollar for it and she offered him a lift from her brother, Stewart Dyke. They were just getting into the car when two police cars came tearing down the dirt road. The polite hunter jumped out and ducked behind a corn crib. Within a few minutes he was dead in her field.

The hunter was Charles Arthur Floyd, America's Public Enemy Number One. To J. Edgar Hoover's Bureau he was a cop killer who'd helped turn a Kansas City car park into a slaughterhouse. To thousands of hard-up farm families in eastern Oklahoma he was the Robin Hood of the Cookson Hills, a local boy who robbed the banks that were robbing them. Neither picture is entirely wrong. Neither is the whole truth either, and ninety-two years on people still can't agree on what happened in that Ohio field.

Quick Answers

Who was Pretty Boy Floyd? Charles Arthur Floyd (1904 to 1934) was a bank robber from Sequoyah County, Oklahoma, linked to around 30 bank robberies and named Public Enemy Number One in 1934.
How did he die? He was shot by FBI agents and East Liverpool police on the Conkle farm near Clarkson, Ohio, at about 4pm on 22 October 1934. He was 30.
Why was he called Pretty Boy? The name's usually credited to a woman in Kansas City in the late 1920s. He hated it and preferred Charley or Choc.
Was he involved in the Kansas City Massacre? The FBI said yes. Floyd denied it until he died, and historians still argue about it.
Where is he buried? Akins Cemetery in Sequoyah County, Oklahoma. His funeral drew at least 20,000 people, said to be the biggest in the state's history.

A Georgia Farm Boy in the Cookson Hills

Floyd was born on 3 February 1904 in Adairsville, Bartow County, Georgia, the son of Walter Lee Floyd and Mamie Echols. When he was seven the family packed up and moved west to Akins in Sequoyah County, Oklahoma, a rough patch of red dirt farms on the edge of the Cookson Hills. As a teenager he picked up work with harvest crews that followed the wheat harvest north through the Plains.

Young Charles Arthur Floyd in a flat cap and jumper with a cigar in his mouth, in a black-and-white photo from his Oklahoma youth — Floyd as a teenager

His first known crime was almost comically small. At 18 he robbed a post office and got away with a haul of pennies. The real trouble came in 1925, when he and two accomplices held up a Kroger grocery payroll in St Louis. He was caught and sentenced to four years in the Missouri State Penitentiary in Jefferson City, and served about three and a half before he was paroled in 1929. Floyd later admitted that prison was where he learned most of what he knew about crime.

Ruby, Jack and a Family Life on the Run

At 20 Floyd married Ruby Hardgraves, and while he was locked up in Missouri she gave birth to their son, Charles Dempsey Floyd, named after the heavyweight champion Jack Dempsey and known as Jackie. Prison wasn't kind to the marriage and Ruby divorced him late in his sentence. It didn't stick. By the early 1930s the two were back together, and Floyd spent stretches living with Ruby and Jackie under false names in Tulsa and Fort Smith.

It was a strange sort of family life. Floyd was also involved with Beulah Baird, and after 1933 he spent months holed up as "Mr George Sanders" with his partner Adam Richetti and the Baird sisters. Ruby, meanwhile, was being watched constantly by lawmen who knew Floyd would come back for his son sooner or later. As one of them found out the hard way, that was exactly what he did.

Sepia photograph of Charles "Pretty Boy" Floyd in a suit sitting close beside his wife Ruby, who wears a fur coat, in the late 1920s — Floyd with his wife, Ruby

Where the Name Pretty Boy Came From

There are several stories about the nickname, and Floyd didn't like any of them. The version that turns up most often puts it in a Kansas City boarding house after his release, where Beulah Baird greeted him during a card game with a cheeky "Hello, pretty boy". Other tellings credit an oil field boss who mocked his smart clothes, or a robbery victim describing the baby-faced young man who'd held him up. Whichever it was, the newspapers loved it and Floyd was stuck with it.

He much preferred Charley, or Choc, a nickname he'd picked up in Oklahoma for his fondness for Choctaw beer, a home brew that was popular in the hills during Prohibition. There's a reported story that when lawmen finally asked him in Ohio whether he was Pretty Boy Floyd, he answered that he was Charles Arthur Floyd. Even dying, he wouldn't answer to it.

The Making of an Outlaw

Floyd's bank robbing career seems to have started in Sylvania, Ohio, on 3 February 1930, which happened to be his 26th birthday. That spring he was arrested in Akron under an alias in connection with a robbery that left Patrolman Harland Manes dead, and later convicted in Toledo of bank robbery and handed 12 to 15 years in the Ohio Penitentiary. He never got there. On 10 December 1930, near Kenton, Ohio, he jumped from the train that was taking him to Columbus and vanished.

The next year was bloody. In April 1931 a shootout in Bowling Green, Ohio, left Patrolman Ralph Castner dead along with Floyd's partner, Billy Miller. That same spring the Ash brothers, two Kansas City rum runners, were found shot dead in a burning car, and Floyd was the chief suspect. Then in July 1931 Prohibition agents raided a Kansas City flower shop and found Floyd in a back room. While they were searching him he pulled a .45 and shot Special Agent Curtis C. Burks, who died two days later, aged 36, leaving a wife and a young son. Floyd shot a bystander and a police officer on his way out of the door and escaped again.

The Ambush at the Farm Gate

If you want to understand why lawmen feared Floyd, the death of Erv Kelley is the place to start. Kelley was a former sheriff of McIntosh County who'd gone to work as a special agent for the Oklahoma Bankers Association, which had armed him with a Thompson submachine gun and put a $4,000 price on Floyd's head. Kelley knew about Floyd's weakness for his family. Ruby had refused his requests to talk her husband into surrendering, so he used her as bait instead.

In the early hours of 9 April 1932, Kelley lay in wait at a farm gate about three miles west of Bixby, Oklahoma, where Floyd was expected for a secret weekend with Ruby and Jackie. He'd brought six experienced lawmen and two deputised farmers, but let most of the professionals take a break, leaving just the two farmers beside him. A car rolled up to the gate with its lights off. When the headlights snapped on they lit Kelley up, and he shouted at the men to halt.

Floyd fired seven times with a .45 automatic and hit Kelley four times, twice in the chest. Kelley's tommy gun fired 14 rounds, most of which kicked up dirt at Floyd's feet. One farmer later said he didn't know how to work his gun and the other said his had jammed. Kelley died where he fell and Floyd, hit in the lower body but not badly hurt, got away with his partner George Birdwell. He didn't deny it afterwards. He told a reporter it was "either him or me, so I let him have it".

The Robin Hood of the Cookson Hills

Here's the odd thing. While the body count was climbing, Floyd's popularity in eastern Oklahoma was going through the roof. The Depression had flattened the state. Cotton prices collapsed, banks failed, farms were foreclosed and whole families were on the road west. A man who robbed banks wasn't an obvious villain to people who'd watched a bank take their land.

The stories spread fast. Floyd was said to tear up mortgage papers during robberies so farmers couldn't be foreclosed on. He made hostages ride on the running boards of the getaway car and let them off once he was clear of town. He left money at farmhouses where he'd eaten or slept, and once returned $140 in traveller's cheques to a family whose car he'd taken. Jeffery S. King's biography, The Life and Death of Pretty Boy Floyd, credits him with paying to feed a dozen families who might otherwise have gone hungry.

Some of that is probably true. Some of it almost certainly isn't. There's no reliable evidence of mortgage burning, and destroying one ledger wouldn't have wiped out a debt anyway, since banks held copies and the loans were recorded elsewhere. But the legend did real work. It's why farm families fed him, hid him in the hills and played dumb when officers came asking. Floyd was following an old tradition there. The same corner of the country had turned outlaws like the Dalton Gang into legends a generation earlier.

Pretty Boy Floyd standing outdoors beside Jess Ring, his wife Ruby's uncle by marriage, in a black-and-white snapshot from the early 1930s — Floyd with Jess Ring, who helped hide him while he was on the run

The Only Interview He Ever Gave

For all the newspaper coverage, Floyd almost never spoke to the press. The one exception came on a November afternoon in 1932. A writer from Muskogee called Vivian Brown had asked for an interview for a book she was working on. Weeks later she came home to find a stranger waiting outside her house. He told her who'd sent him and she got into his car.

They drove about thirty miles over country roads without saying much and pulled up in a secluded pecan grove, where a tan Ford V-8 was waiting. Floyd, then carrying a $6,000 bounty, introduced himself and talked to her for hours while she took it all down in shorthand. He told her about the Georgia farms, the harvest crews and what prison had taught him. He insisted he'd never killed anyone unless he was forced to by a trap. And he had a neat line on the bank jobs, saying the money was bonded so the only people who lost out were the big boys. By Oklahoma Today's account it's the only proper interview he ever gave.

A Kidnapped Sheriff and the Kansas City Massacre

On 16 June 1933, Floyd and Richetti were limping towards Kansas City when their car broke down in Bolivar, Missouri. They pulled into the local Chevrolet garage, and as luck would have it, in walked Sheriff Jack Killingsworth of Polk County. Richetti grabbed a machine gun, Floyd drew two .45s and they bundled the sheriff into another car. They drove him north and let him go unharmed at Deepwater, then reached Kansas City at about 10pm.

The next morning, 17 June 1933, lawmen brought a captured fugitive called Frank "Jelly" Nash off the train at Union Station to drive him back to Leavenworth. As they loaded him into a Chevrolet outside the east entrance, gunmen opened up with machine guns. The whole thing lasted about 30 seconds. Kansas City detectives Frank Hermanson (42) and William Grooms (29) were killed, as were McAlester police chief Otto Reed (49) and Bureau of Investigation agent Raymond Caffrey (31). So was Nash, the man the gunmen had supposedly come to rescue.

The Bureau named Vernon Miller as the organiser and Floyd and Richetti as his accomplices. Richetti's fingerprints were found on beer bottles at Miller's house, and some witnesses picked out Floyd. But the case has never sat comfortably. Floyd's family said he admitted plenty of crimes but always denied this one. A postcard signed "Charles Floyd" reached Kansas City police denying any part in it, and the family's obituary page notes that the shoulder wound one gunman was supposed to have taken was never found on his body. Historian Robert Unger has argued that agents had blown the secret transfer themselves by briefing a reporter, and both Unger and Michael Wallis have questioned whether Floyd and Richetti were there at all.

Miller was found beaten and strangled in a ditch outside Detroit in November 1933. The local mob boss John Lazia, who many in Kansas City suspected was behind the attack, was shot dead in his own driveway the following July. Whoever really pulled the triggers, the massacre was a gift to Hoover. It became his best argument for arming his agents and giving the Bureau real national powers, a push that had already been gathering pace since the Lindbergh kidnapping.

Public Enemy Number One

1934 was the year the Public Enemy era ended in gunfire. Bonnie and Clyde were ambushed in Louisiana by Frank Hamer's posse in May. John Dillinger, the man who'd walked out of Crown Point jail with a wooden gun that March, was shot outside the Biograph Theater in Chicago on 22 July. With Dillinger gone, Hoover handed the Public Enemy Number One title to Floyd. Some of Floyd's contemporaries were paying underworld surgeons to change their faces by then. Floyd mostly relied on the Cookson Hills.

Hoover later claimed that Floyd had at one point offered to give himself up if he was spared the death penalty. Nothing came of it. By the autumn Floyd and Richetti were in Buffalo, New York, with the Baird sisters when they decided to head home to Oklahoma.

Fog, a Telephone Pole and a Gunfight

They left Buffalo on the evening of 18 October 1934. Shortly after midnight, in thick fog south of Youngstown, Floyd drove into a telephone pole. Nobody was hurt but the radiator was punctured. The women went to find a mechanic and get the car towed while the men hid in the woods near Wellsville. Accounts disagree on whether what came next happened on the 19th or the 20th, but a local man called Joe Fryman spotted two men in suits lying in the scrub and told the police.

Wellsville police chief John Fultz went to check with two other men. Richetti bolted into the brush, Floyd opened fire and in the confusion one lawman was shot in the foot. Floyd escaped over a ridge. Richetti was caught, disarmed and gave a false name, but Fultz recognised him at the station and put out the alert. Melvin Purvis, the Chicago agent who'd led the Dillinger hunt, arrived with his men, and for the next two days lawmen combed the area for Floyd.

The Last Afternoon on the Conkle Farm

By Monday 22 October he was hungry, tired and out of options, which is how he ended up at Ellen Conkle's door. When the two cars came down Sprucevale Road, one held four Bureau agents under Purvis and the other four East Liverpool officers under Police Chief Hugh McDermott. Floyd broke from behind the corn crib and ran zigzagging across the field towards a line of trees, glancing back over his shoulder as eight men shouted at him to stop.

The shooting started. Floyd went down. When the officers reached him he told them, "I'm done for, you've hit me twice". He confirmed who he was but refused to say anything about Kansas City. He was carried to the shade of an apple tree and was dead within minutes. In his pockets they found about $120. He had two Colt .45 automatics on him and, by the East Liverpool library's account, hadn't fired either of them.

He also had a pocket watch with a fob, and on the fob and a lucky coin he carried were groups of notches. Plenty of people, Hoover's Bureau included, took them for a tally of men he'd killed. Maybe they were. Nobody ever proved it, and Floyd wasn't around to ask.

Chester Smith, one of the East Liverpool men, went home late for supper that evening. His daughter later remembered him saying he didn't have time to eat because he'd just shot Pretty Boy Floyd. He washed, changed his clothes and went back to work.

Who Really Shot Pretty Boy Floyd?

For 45 years the official story was simple. Purvis's men fired as Floyd ran and he died of his wounds. Then in 1979 Chester Smith, by now an 84-year-old retired police captain, told Time magazine something very different. He said he'd fired first with his own .32 Winchester rifle, having refused the gun he was issued, because "I knew Purvis couldn't hit him". Smith claimed his two shots brought Floyd down wounded but alive. He said he disarmed him, that Purvis told him to step back so he could question Floyd and that when Floyd wouldn't talk, Purvis ordered agent Herman Hollis to fire into him with a tommy gun.

The FBI has rejected the story ever since, and its point-by-point rebuttal is fairly convincing. It says the bullets that killed Floyd didn't match Smith's rifle, and that the coroner found no close-range machine gun wound to the chest. Smith's own statement the day after the shooting didn't claim he'd felled Floyd, and the sworn statements of the other three local officers back the Bureau's version. Most damning of all, Bureau records and Smith's 1934 statement both suggest Hollis wasn't even there. Hollis couldn't defend himself by 1979. He'd been killed in a gunfight with Baby Face Nelson in November 1934, just five weeks after Floyd.

Smith's story has a strange afterlife of its own. In 1982 he showed a collector called Neal Trickel a Colt pistol he said was one of the two Floyd carried, along with a .45 bullet he said had come out of Floyd's body, and gave him both. That pistol later went up for auction at Rock Island with an estimate of $10,000 to $20,000. Whatever you make of Smith's account, he clearly wasn't short of souvenirs.

Ten Thousand People Through a Funeral Home Door

Floyd's body was taken to the Sturgis Funeral Home in East Liverpool. His mother, Mamie, wired the police chief asking that her son not be put on public display. Nobody listened. That night the crowd was so big that more than 10,000 people filed past him between 8.30pm and 11.15pm, about 50 a minute. When the doors couldn't cope, people stormed the place. The porch railing was ripped off, the shrubbery flattened and the lawn wrecked. The next morning his body left town in a railway baggage car bound for Oklahoma.

Before it went, a death mask was made of his face. The body went home but the mask stayed behind in Ohio. For years it hung on the wall of the Sturgis House basement above the washing machine, where the building had become a bed and breakfast and a small mortuary museum. It's since been donated to the East Liverpool Police Museum in the old city jail, where you can see it by appointment.

The Biggest Funeral in Oklahoma History

Back home in Sallisaw his body was put on show again, and this time the numbers were staggering. When he was buried at Akins Cemetery on 28 October 1934, estimates of the crowd ran from 20,000 to 40,000, and it's still described as the biggest funeral Oklahoma has ever seen. Time later pointed out that the agents who'd hunted him weren't among the mourners.

Thousands of mourners packed onto a wooded hillside for Pretty Boy Floyd's funeral in Akins, Oklahoma, in October 1934 — The crowd at Floyd's funeral in Akins, Oklahoma

For a man who drew that kind of crowd, the grave is surprisingly modest. He lies under a small headstone alongside his parents. It's had a rough time over the years. Souvenir hunters damaged it and the headstone was reportedly stolen in 1985. Back in Ohio, a roadside marker put up near the Conkle farm in 1993 was stolen in 1995 and turned up a couple of weeks later in a wooded lot in town. The marker that stands there now on Sprucevale Road carries what look like bullet dents.

What Happened to Everyone Else

Adam Richetti was tried in Kansas City for the murder of Detective Frank Hermanson, convicted and sentenced to death. That sentence was overturned and he was condemned a second time. On 7 October 1938 he died in the Missouri State Penitentiary's new gas chamber in Jefferson City, still insisting neither he nor Floyd had been at Union Station. He's often described as the first man gassed in Missouri, but he wasn't. Executed Today counts him as the fifth. His last meal was the same as the prison staff ate that day: steak, eggs, potatoes, aubergine, corn, pineapple, biscuits and cake. Mississippi's later struggles with the method are a story of their own, told in our piece on Jimmy Lee Gray.

Front and side mugshot of a man in a suit on a prison record card listing his name, crime and sentence, black and white

Melvin Purvis was the most famous lawman in America by the end of 1934, which turned out to be his undoing. Hoover couldn't stand being upstaged and Purvis left the Bureau in 1935. He died of a gunshot wound at his home in South Carolina in 1960, ruled a suicide. As for Hoover, he spent the rest of his life telling the story of the gangster years his way, with his Bureau as the hero.

How a Song and a Novel Kept Him Alive

Floyd might have faded into the crowd of 1930s bank robbers if it hadn't been for two men who never met him. In 1939 John Steinbeck gave him a cameo in The Grapes of Wrath, where Ma Joad remembers him as a decent boy from a decent family who was hounded by the law until he turned mean. Steinbeck's Joads were the same kind of displaced Okies who'd once sheltered the real man, the people Dorothea Lange was photographing on the roads to California.

Then Woody Guthrie wrote Pretty Boy Floyd, recorded for his 1940 album Dust Bowl Ballads. Guthrie had grown up in Okemah, Oklahoma, and he told the folklorist Alan Lomax that farmers protected Floyd because they felt he'd never had a fair shake. The song is the main reason anybody outside Oklahoma still knows his name. Its most famous idea, that some men rob you with a gun and some with a pen, sums up the Robin Hood legend better than anything Floyd ever said himself.

https://www.youtube.com/watch?v=G4YKUJZI5Bg

What Holds Up and What Doesn't

The mortgage burning: No reliable evidence. It's folklore, and it tells you more about how people felt about banks than about Floyd.
The generosity: Likely real in part. Meals paid for, money left at farmhouses and families fed all turn up in multiple accounts, and King's biography takes them seriously.
The killings: Real. Floyd admitted killing Erv Kelley, and agent Curtis Burks and several Ohio officers died in shootings he was involved in.
Kansas City: Unproven either way. The Bureau was certain, Floyd denied it to the end and serious historians have their doubts.
The notches: Suggestive, but nobody knows what they meant.
Chester Smith's execution story: The FBI's evidence against it is strong, but it's never quite gone away.

Floyd was a violent man who chose armed robbery and kept choosing it. Officers died because of that, and their families deserve to be part of his story too. But he was also a product of a very particular moment, when the banks seemed like the real thieves and a polite stranger who paid a dollar for his dinner could look like justice. People have always had a soft spot for a charming crook, as the Kray twins would prove in London thirty years later. Floyd just happened to come along when a whole state needed one.