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Remembering Pretty Boy Floyd
news
October 28, 2025
Remembering Pretty Boy Floyd
91 years after his violent death
By LYNN ADAMS SPECIAL TO THE REGISTER,

In depths of the Great Depression and the Dust Bowl, many Oklahomans existed on almost nothing. High unemployment, bank failures and farms that dried up and blew away were daily reminders for Okies of their debilitating hopelessness.

About the only thing the downtrodden had to look forward to was migration to the promises California held, but which were too often futile.

In eastern Oklahoma, for many there was no work, no food, no way out of desperate poverty, no future, no way tomorrow would be different than the previous day.

But some — maybe many — were touched by an unlikely savior, an unimaginable benefactor. Some even thought of the rogue champion as their modern-day Robin Hood.

After all, there were newspaper and local accounts from the early 1930s that helped build his enduring myth — the destruction of mortgage documents and loan papers, erasing debt for struggling homeowners — although historians debate the scale of his benevolence, arguing that rather than lifechanging effects being wide-spread, his reversal of fortunes for Oklahomans were believed sporadic at best.

But legends are sometimes built on fragile footing, and memories are shaped by retellings and embellishments.

There’s no discounting, however, the almostcult- like reputation of local folk-hero Charles Arthur Floyd, the legendary bank robber widely known as “Pretty Boy” Floyd, although the outlaw hated the moniker.

That’s why 91 years ago Tuesday, at a time when the population of Sequoyah County was about 20,000, mourners estimated to be as many as 40,000 — the largest funeral attendance in Oklahoma history — descended on the Akins c ommu n i t y where Floyd grew up and was buried in 1934.

But the reverence singularly reserved for remembering the dearly departed devolved into an unruly free-for-all, according to news reports, as horse-drawn wagons and even a school bus jammed roads leading to the rural hilltop cemetery. Additionally, in the mad scramble to get a peek at Floyd, reports are that graves were trampled, flowers were crushed and foot stones were toppled. There were even instances where onlookers brought picnic lunches that were eaten off tombstones, while others jockeyed for a glimpse or even a souvenir photo.

It was Oklahoma’s tribute to America’s Public Enemy No. 1. After all, there wasn’t much to capture the imagination of the destitute public, and accounts of the notorious gangster robbing from the rich and giving to the poor was an aweinspiring tale of one of Oklahoma’s own.

Floyd’s life of crime

Born in 1904 in Georgia, Floyd’s family moved to Akins when he was about 7-years-old. But his parents were dirtpoor, and his father spent most of his time trying to avoid foreclosure. When drought, plagues and dust storms all but eliminated farm production, the family turned to bootlegging.

By the 1920s when he was 18, Floyd pulled his first hold up — netting $350 in pennies from a post office. For the fledgling outlaw, it was “easy money,” and when he was suspected of the crime, his father gave him an alibi.

From there it was a short journey to infamy with a string of robberies across the Midwest.

But infamy transitioned into legend when stories told by families claimed their mortgages vanished after one of Floyd’s bank jobs. The unexpected good fortune for desperate Americans came at a time when banks were foreclosing on farms and homes at an alarming rate, and Floyd was viewed less as a thief than as someone striking back at institutions that were causing so much misery.

In 1921, Floyd married 16-year-old Ruby Hargrove, and they had a son. But money was scarce, so Floyd left home seeking work. When his search proved futile, he took the train to St. Louis where he robbed a Kroger store of about $16,000.

But his sudden lavish lifestyle raised suspicions, and he ended up in the Jefferson City Penitentiary, where he served three years. That’s when he vowed never to be locked up again.

Known as the Robin Hood of the Cookson Hills, Floyd’s reputation was in the tradition of Jesse James, Billy the Kid and John Dillinger. But he was neither highly intelligent nor polished, relying on his cool demeanor, shrewd cunning and expert gun-handling ability. His generosity and honesty were legendary among those he rescued from financial ruin, with many people helping him elude the police.

Once he reportedly left a large contribution at an Oklahoma church, and no one reported his visit. Another story claims that he kept a rural school in fuel one winter.

Although he attended church regularly, his was a life of crime. In 1931 and 1932, he robbed so many banks in Oklahoma that bank insurance rates doubled. He used a submachine gun and wore a bulletproof vest. He usually worked alone, and rarely concealed his identity.

His crime spree ends Floyd met a violent end in 1934, when he was killed in an FBI ambush in Ohio. But his reputation as the outlaw who fought the banking system lived on in folk songs, ballads and Depression-era lore. Floyd came to symbolize resistance against a system many felt had failed them, proof that even in desperate times, a single dramatic gesture could leave a lasting mark on history.

In a newspaper account following his death, the Sequoyah County Times reported that “he was shot to death in a burst of fire from two machine guns and rifles in the hands of federal agents and police as he made his final effort to escape. Four bullets struck him, two in the back, another in the side and one in the arm. He died minutes later. An automatic pistol was in Charles Floyd’s hand when he fell mortally wounded.”

The end came on Oct. 22, 1934, when Floyd stopped at the farmhouse of Ellen Conkle and asked for something to eat. He was dressed in a dark suit, and wore a white shirt, but it was very dirty.

Conkle, a widow who said Floyd “was a very pleasant man,” fixed him a dinner of spare ribs, potatoes, rice, pumpkin pie and coffee.

“He ate it like he really enjoyed it, and then he gave me a dollar,” Conkle said in her eyewitness account published by United Press International. “I didn’t want to take it, but he said the dinner was fit for a king and I must take it, so I did. I will save that dollar.”

Conkle said she didn’t know who he was “because I don’t read much of that kind of thing in the papers. He seemed awfully interested in the newspapers, however. I got him a copy of yesterday’s paper.” “He seemed a little nervous, but I didn’t think much of it. He went to the road once or twice and looked up and down,” she said.

“My brother Stuart Dikes from Rogers and his wife came in from the fields. They had been husking corn for me all day. Floyd asked my brother if he would drive him back to Highway 7, but he didn’t say where he wanted to go from there. He said he didn’t much care when he went because he had been drunk.”

Conkle said her brother and sister-in-law got in the car with Floyd and started to back it from behind the corn crib. But just as they did, “two cars drove up to the end of the lane, about 100 feet away from my brother’s car.”

Floyd saw them and told Dikes, “drive back behind the crib quick. They are after me!” Dikes did, and when he stopped the car, Floyd told him to “get out and run. Floyd then jumped out and started to run across the field. The federal men jumped out of their car and ran after him. As they passed my brother, they asked him who the man was, and my brother replied he did not know. So they started shooting,” Conkle said.

“Floyd shot a couple of times at them, but I don’t think he hit anybody. Floyd ran about 200 feet across my field before he fell.”

A marker was erected in 1993 along Sprucevale Road between the Ohio towns of East Liverpool and Rogers at the location of the Conkle farm to mark for all time where America’s Public Enemy No.1 was shot. The marker was stolen in August 1995 and recovered about two weeks later. It was re-erected on the same site.

The year before at the Akins Cemetery, Floyd had told his mother: “Right here is where you can put me. I expect to go down soon with lead in me. Maybe the sooner the better. Bury me deep.”

Although Floyd’s mother did not want her son’s body viewed by the public, by the time the funeral home received her wishes, a mob of more than 10,000 people had stormed the funeral home, trampling shrubbery and destroying the lawn in an effort to get a final glimpse of the notorious criminal.

In the years since 1934, Floyd’s headstone at the cemetery has been desecrated by souvenir hunters, and was stolen in 1985. A new headstone now marks his grave.

A final tribute?

Although it’s been more than nine decades since his death, Pretty Boy Floyd has not been forgotten, especially in Sequoyah County.

To honor his memory, an abstract artwork piece depicting the different ways in which Floyd has been viewed in history will be unveiled at the third annual Red Autumn Art Festival at an 11:45 a.m. ceremony on October 31.

“Some people view him as a thug, some people view him as a Robin Hood, and all of those points of view the artist tried to capture in this work,” says Lance Montgomery, Red Autumn organizer and president of the Sallisaw Main Street organization.

The artwork was completed by the pop artist known professionally as Ghost — “that’s his art name,” Montgomery says — who has had his works “displayed at New York Fashion Week, Universal Studios and galleries and shows from Chicago to Los Angeles to Austin, Texas to New York.”

The tribute work was paid for 100% by Sallisaw Main Street, and will be mounted at the pocket park in downtown Sallisaw.

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