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Pretty Boy Floyd


Charles Arthur "Pretty Boy" Floyd (February 3, 1904 – October 22, 1934) was an American bank robber and fugitive who operated in the Midwest during the era. Born near Adairsville in , as the second son and fourth of six children to Walter Lee Floyd and Mamie Helena Echols Floyd, he relocated with his family in 1911 to , near the border.
Floyd's criminal career began with bootlegging and minor offenses in his teens, escalating to a 1925 payroll robbery in that resulted in a five-year prison sentence from which he was paroled in 1929; thereafter, he was linked to over 30 bank robberies, including the 1932 holdup of the Sallisaw State Bank in . He earned his "Pretty Boy" moniker due to his youthful good looks and was suspected by the FBI of participating in the June 17, 1933, , which killed four officers, though subsequent evidence has disputed his direct involvement.
Following John Dillinger's death, FBI Director named Floyd Number One, prompting an intense nationwide manhunt for his role in armed robberies and killings. On October 22, 1934, Floyd was fatally shot by FBI agents and local officers in a cornfield near East , , after a chase; his funeral drew over 20,000 mourners, reflecting his status as a in some rural areas, mythologized in works like Woody Guthrie's ballads as a sympathetic figure against economic despair, despite his violent record.

Early Life and Background

Birth and Family Origins

Charles Arthur Floyd was born on February 3, 1904, near Adairsville in . His parents, Walter Lee Floyd and Minnie Floyd, were tenant farmers struggling with poverty in rural . Floyd was the second son and fourth of six surviving children in the family, which included siblings from a large household marked by the hardships of life. The Floyds descended from farming stock in the American South, with no recorded history of prior criminal involvement among immediate relatives, though economic pressures shaped their early circumstances. His father and mother maintained a law-abiding existence amid the agrarian challenges of the early .

Relocation to Oklahoma and Formative Years

In 1911, when Charles Floyd was seven years old, his family left the rural hills of , seeking better economic prospects amid limited farmland opportunities, and relocated to the Cookson Hills region near Sallisaw in the newly established state of . The Floyds, including parents Walter Lee Floyd—a —and Helena Ranier Floyd, joined relatives and acquaintances already settled in County, where they continued subsistence farming on rented land amid challenging soil and frequent crop failures. This move reflected broader patterns of southern migration to the during the early , driven by hopes of fertile land, though the family encountered persistent poverty and harsh living conditions typical of households. Floyd spent his formative years in the small community of Akins, a rural outpost where he contributed to family labor on the , tending crops and from a young age. The household's six surviving children, of which Floyd was the fourth, faced economic hardship exacerbated by Oklahoma's volatile agricultural economy, including droughts and low prices that kept the family in to landowners. Local accounts describe Floyd as physically striking and athletic, earning him the nickname "Pretty Boy" among peers for his handsome features and charm, traits that contrasted with the drudgery of life. was limited; Floyd attended a one-room schoolhouse intermittently, prioritizing farm work over formal learning, which left him with basic literacy but little advanced schooling. These years instilled in Floyd a familiarity with the rugged terrain of the Cookson Hills, which later served as a hideout during his , while the pervasive and perceived inequities in land tenancy fostered resentment toward —though no direct evidence links this to his later choices beyond contemporaneous economic pressures. By his late teens, Floyd had developed a reputation for minor mischief, such as bootlegging and petty , amid the broader social ferment of post-World War I , where Prohibition-era opportunities intertwined with farm distress. His early adulthood involved sporadic employment as a farmhand and mechanic, but persistent financial strain marked the transition from adolescence to independence.

Descent into Crime

Bootlegging and Minor Offenses

In his late teens, Floyd supplemented income from seasonal harvesting in and by producing and distributing corn liquor, capitalizing on demand during national (1920–1933). He had learned the distillation process for during his youth in rural County, where homemade alcohol was common among farming communities. By the early 1920s, Floyd's involvement extended to bootlegging operations in , where he networked with underworld figures, including mentor John "Red" Lovett, who introduced him to more structured criminal methods beyond liquor trafficking. In 1924, shortly after marrying Ruby Hardgrave on , he traded five gallons of for a pearl-handled , illustrating his active role in the illicit trade. Floyd's minor offenses began around age 16 ( 1920), encompassing petty disturbances and initial encounters typical of transient laborers in the region, though specific charges were often or public disorder rather than formalized bootlegging violations. These activities, while not resulting in significant incarceration at the time, eroded his adherence to legitimate work and fostered associations that escalated his criminal trajectory. No federal records document bootlegging arrests for Floyd prior to his felony, reflecting the decentralized enforcement of Prohibition-era laws.

First Felony Conviction and Prison Time

On September 11, 1925, Charles Arthur Floyd participated in an armed payroll in , , targeting a shipment valued at $11,929 from a Employees Benevolent Association payroll. Accompanied by accomplices, including his associate Walter Renfro, Floyd held up the courier at gunpoint, marking his escalation from petty bootlegging to . Floyd was arrested five days later on September 16, 1925, by police for highway robbery, his first charge. He pleaded guilty, receiving a five-year to the on December 19, 1925. While incarcerated as inmate #22318, Floyd largely avoided further disciplinary issues, engaging in routine prison labor. He served approximately three years before in March 1929, having earned time off for good behavior. Upon release, Floyd reportedly vowed never to return to , a resolve that propelled his subsequent criminal activities. This conviction solidified his status as a felon, prohibiting ownership under and intensifying his path during Prohibition's waning years.

Major Criminal Activities

Bank Robbery Operations

Charles Arthur Floyd's operations commenced shortly after his parole from the on December 10, 1929. He and a small group of associates targeted rural banks in and , employing tactics that emphasized speed, intimidation with handguns and sawed-off shotguns, and vehicular getaways to minimize confrontation and maximize escape opportunities. These operations typically yielded modest sums, ranging from a few hundred to several thousand dollars, reflecting the limited cash reserves in small-town institutions during the early . The first documented robbery attributed to Floyd occurred on February 5, 1930, at the Farmers and Merchants Bank in , where he and accomplices entered armed and fled with cash from the vaults. Floyd was arrested in connection with this heist on May 20, 1930, in , and pleaded guilty to assault with intent to rob on November 24, 1930, receiving a sentence of 12 to 15 years. While free on bond pending transfer, he participated in the robbery of the Citizens Bank in , on December 12, 1930, securing approximately $300. Floyd escaped custody en route to the shortly thereafter, resuming operations as a . In 1931, Floyd's activities intensified in , often in collaboration with associates like George Birdwell. On March 9, his gang robbed the in Earlsboro of $3,000. Further heists followed in locations such as Konawa and Wellston in April, and the Exchange Bank in El Reno on June 19, netting around $3,000. By late 1931, the pace accelerated, including a double on December 12 of banks in Paden and , executed in a single day using submachine guns for added firepower. These operations strained local banking security, prompting elevated insurance rates across amid fears of Floyd's gang. While popular accounts inflate the total to dozens, verifiable incidents number in the low teens, concentrated in underserved rural areas where response was delayed.

Involvement in the Kansas City Massacre

The occurred on June 17, 1933, at in , when gunmen ambushed a group of officers escorting federal prisoner "Jelly" Nash back to Leavenworth Penitentiary after his recapture in . The attack resulted in the deaths of four individuals: FBI Special Agent Raymond J. Caffrey, detectives W.D. Grove and Hermanson, and Nash himself, who was caught in the crossfire. The perpetrators used submachine guns and pistols in a brazen daylight assault, fleeing after the shooting left bystanders and survivors in chaos. Authorities quickly implicated Charles "Pretty Boy" Floyd alongside and as key figures in the attempted rescue of Nash, a longtime associate of Floyd from earlier criminal circles. The FBI, under , cited Floyd's known connections to Miller—a former sheriff turned gunman who organized the plot—and Richetti, as well as unverified eyewitness identifications and Floyd's reputed presence in the Kansas City area around the time. This attribution elevated Floyd's status in the public eye, contributing to his designation as one of the first "Public Enemies" and justifying expanded federal powers under new legislation like the 1934 anti-racketeering laws. However, initial suspicions relied heavily on circumstantial associations rather than direct forensic or eyewitness linkages to the shooting itself. Floyd vehemently denied any participation, dispatching a postcard postmarked from Springfield, Missouri, to Kansas City Police Captain William Higgins shortly after the event, stating: "I—Charles Floyd—want it made known that I did not participate in the massacre of officers at Kansas City." Contemporary skeptics, including Higgins, argued the massacre's sloppy execution did not align with Floyd's more calculated bank robbery style. Later historical investigations, including testimony from criminals like Blackie Audett identifying Miller, Maurice Denning, and Solly Weisman as the shooters, further undermined the claims. Subsequent evidence has confirmed that neither Floyd nor Richetti directly participated in the , with primary responsibility attributed to and possibly an unidentified third accomplice known as "Lamar." Richetti's later arrest with Floyd in 1934 stemmed from unrelated traffic stops, not forensics, and his conviction rested on proximity to rather than scene-specific proof. The FBI's emphasis on Floyd's involvement appears driven by institutional incentives to consolidate authority amid Depression-era crime waves, rather than irrefutable facts. Floyd reiterated his innocence until his death on October 22, 1934, maintaining to agents that he had no role in the killings.

Pursuit and Demise

Escalation of Federal Involvement

The Kansas City Massacre on June 17, 1933, significantly heightened federal scrutiny of Charles Arthur "Pretty Boy" Floyd. At Union Station in Kansas City, Missouri, gunmen—suspected to include Floyd, Vernon Miller, and Adam Richetti—attempted to free federal prisoner Frank "Jelly" Nash from custody, resulting in a shootout that killed four law enforcement officers, including two federal agents from the Bureau of Investigation (BOI). Although Floyd consistently denied participation, the Bureau attributed the attack to him, framing it as a direct assault on federal authority during a period of rising gangster violence. This incident, which claimed the lives of Special Agent Frank J. Smith and Bureau of Investigation operative Frank Hermans, spurred immediate congressional action to empower federal law enforcement. In response to the massacre, Congress enacted reforms that bolstered the BOI's capabilities, including the of 1934, which regulated machine guns and other weapons commonly used by criminals, and amendments allowing agents to carry firearms and make arrests without local warrants in interstate cases. These changes, driven by public outrage over the killings of federal officers, shifted the pursuit of figures like Floyd from primarily local efforts to a coordinated federal priority under Hoover's direction. The Bureau expanded its resources, coordinating with state police and offering substantial rewards, transforming Floyd into a symbol of the era's "public enemy" threat. Floyd's status escalated further after the death of on July 22, 1934, when Hoover officially named him Number One, surpassing other fugitives in priority. A $23,000 reward—dead or alive—was posted, reflecting the Bureau's determination to eliminate him amid suspicions of multiple bank robberies and killings tied to his operations. This designation intensified the , with federal agents deploying advanced surveillance and cross-state raids, culminating in heightened pressure that forced Floyd into constant evasion across the Midwest. Despite debates over his direct role in events like the massacre, the federal narrative solidified his image as a ruthless outlaw warranting extraordinary measures.

Final Evasion and Confrontation

On October 20, 1934, Floyd and associate were traveling near , when their vehicle stalled, prompting intervention by local police. Police Chief John Fultz, along with officers Grover Potts and William Erwin, approached, leading to a in which Richetti was wounded and captured while Floyd escaped after shooting Potts and commandeering a passing motorist's car to flee toward . Floyd evaded the ensuing manhunt overnight, which involved federal agents led by joining local authorities across Columbiana County. The next morning, October 22, he arrived at the farmhouse of Ellen Conkle in Sprucevale, near , where he requested food and transportation; a nearby farmer observed him and alerted . , including Purvis, East Liverpool Chief of High J. McDermott, and officers Chester C. Smith, Glenn Montgomery, and Herman Roth, quickly converged on the property. Upon , Floyd fled on foot across a cornfield toward wooded cover, pursued by approximately nine officers who discharged around 93 rounds. Struck by three bullets—two in the torso and one in the arm—he collapsed beneath an . Purvis approached the fallen outlaw, who confirmed his identity as Charles Floyd before dying approximately 15 minutes later from his wounds. FBI agents R.J. Caffrey, , and Charles Winstead were among those who fired during the exchange, though accounts vary on the specific fatal shots. Floyd's body was transported to Sturgis Funeral Home in East , where it drew over 10,000 viewers before shipment to for burial.

Criminal Impact and Accountability

Documented Crimes and Fatalities

Charles Arthur Floyd's criminal record includes a 1925 conviction for robbing a United States mail payroll truck in , , on September 11, where he and accomplices stole approximately $13,000 at gunpoint; he was arrested two days later, pleaded guilty, and received a five-year sentence in the . After his on June 10, 1929, Floyd was strongly suspected of murdering Jim C. Mills, a neighbor who had fatally shot Floyd's father in a 1927 land dispute and was acquitted; Mills vanished shortly after Floyd's release, with his body never recovered, and attributed the killing to Floyd based on and Floyd's prior threats. Floyd's subsequent activities centered on armed bank holdups, often with accomplices like George Birdwell, targeting small-town institutions across , , , and between 1930 and 1933; documented examples include the robbery of the Sloan State Bank in , in early 1930, netting several thousand dollars; the Bank of Earlsboro in Earlsboro, Oklahoma, on March 9, 1931; the Sallisaw State Bank in , later in 1931; and simultaneous holdups of banks in Paden and , Oklahoma, on December 12, 1931, using submachine guns and bulletproof vests. These operations typically involved threats of but few direct fatalities during the robberies themselves, with Floyd's escaping with sums ranging from $1,000 to $4,000 per , contributing to his evasion of capture for years. Fatalities directly linked to Floyd occurred in shootouts with pursuing him. On April 25, 1931, during an attempted bank robbery in , Floyd and Birdwell exchanged fire with police, killing Patrolman R. H. Castner; Floyd was wounded but escaped. On June 17, 1932, near Slick, , Floyd engaged in a gun battle with former McIntosh County Sheriff Ervin A. Kelley, a attempting an ambush; Kelley was shot multiple times and died at the scene, while Floyd sustained four wounds but fled. Federal authorities also indicted Floyd for the June 17, 1933, , in which four officers and a criminal associate died during an attempted , but ballistic evidence was inconclusive, Floyd denied involvement in a written statement to the AP, and no conviction occurred before his death. Overall, while sensationalized accounts attribute up to a dozen killings to Floyd or his associates, verifiable direct fatalities number at least three, all in defensive or retaliatory exchanges rather than premeditated executions.

Examination of the Robin Hood Myth

The myth portrays Charles Arthur "Pretty Boy" Floyd as a Depression-era who selectively robbed affluent banks, destroyed records to aid indebted farmers, and distributed proceeds to the impoverished, thereby challenging exploitative amid widespread foreclosures. This narrative emerged prominently in folklore, where Floyd's rural roots and charm fostered sympathy among tenant farmers and the unemployed, amplified by ballads like Woody Guthrie's 1939 song "Pretty Boy Floyd," which explicitly likened him to the legendary English bandit. However, such depictions conflate economic grievances with unsubstantiated personal benevolence, as no contemporaneous records or eyewitness accounts verify acts of charity or mortgage destruction. Empirical examination reveals Floyd's operations lacked the discriminatory ethos attributed to him; he targeted over 30 banks across the Midwest from to , including small rural institutions whose depositors were often local working-class residents rather than distant elites. Anecdotal claims of sparing "farmers' deposits" or paying for strangers' meals persist in oral histories, but these derive from post-mortem embellishments by sympathizers, with no forensic or financial —such as recovered funds traced to recipients—substantiating redistribution. Floyd's documented expenditures prioritized evasion, associates, and family support, including remittances to his wife and son, rather than broad ; federal investigations, including FBI files, uncovered no charitable patterns amid his $23,000-plus in verified heists. The myth's endurance stems from causal alignments during the , when bank failures and evictions fueled class antagonism, rendering outlaws like Floyd proxies for systemic critiques—yet this overlooks his role in escalating violence, including the April 9, 1932, killing of lawman Erv Kelley and suspected ties to other fatalities. Even Floyd's son, Charles Floyd Jr., later distanced the family from heroic legends, emphasizing the man's criminality over folklore. Historians attribute the archetype to romanticized underdog narratives, akin to those surrounding , but grounded analysis prioritizes verifiable predation: Floyd's gangs netted personal gains through intimidation and shootouts, not equitable redistribution, underscoring how public sentiment can eclipse evidentiary reality.

Perception and Cultural Legacy

Regional Folk Hero Narrative

In rural , particularly the Cookson Hills region of eastern Oklahoma where Floyd spent much of his youth after his family relocated from in 1911, he cultivated a reputation as a amid the economic hardships of the . Locals romanticized Floyd as the "Robin Hood of the Cookson Hills" or "Sagebrush Robin Hood," portraying him as an who targeted exploitative banks responsible for widespread farm foreclosures, allegedly destroying mortgage documents during robberies to relieve indebted farmers of their obligations. This narrative gained traction because Floyd reportedly distributed small sums of cash to impoverished residents and avoided harming ordinary citizens in holdups, fostering sympathy among those who viewed financial institutions as the true predators amid 25% and devastation by 1933. The image persisted through oral traditions and ballads, such as Woody Guthrie's song "Pretty Boy Floyd," which depicted him as a sympathetic figure rebelling against "" bankers who "robbed you with a six-gun" less honorably than outlaws like Floyd. Community anecdotes from the era, including claims of residents providing Floyd shelter, food, or directions to evade lawmen between 1932 and 1934, reinforced this view, with some families boasting of encounters as badges of regional pride against federal overreach. However, contemporary accounts from locals and later historical analyses indicate these acts of aid stemmed more from fear of or cultural defiance of distant authorities than verified benevolence, as Floyd's gang prioritized personal profit over systematic redistribution. Empirical evidence for the core Robin Hood claims remains anecdotal and unverified; no bank records or eyewitness testimonies conclusively document Floyd destroying papers or donating robbery proceeds en masse, suggesting the amplified isolated gestures to symbolize broader agrarian during a period when over 1 million farms faced nationwide from 1930 to 1935. This regional narrative contrasted sharply with national perceptions, where Floyd's designation as "" by in 1934 after John Dillinger's death emphasized his role in violent crimes like the 1933 , yet endured locally as a cautionary emblem of defiance against economic elites.

Representations in Media and Historiography

Charles Arthur Floyd has been depicted in various films and television productions, often romanticizing his life amid the economic hardships of the . In the 1960 film Pretty Boy Floyd, directed by Herbert J. Leder, portrays Floyd as a reluctant drawn into by circumstance, emphasizing his charm and evasion of capture over his violence. The 1970 low-budget film A Bullet for Pretty Boy, starring , similarly frames Floyd as a folk anti-hero, focusing on his roots and bank heists while downplaying confirmed killings. Television adaptations include Martin Sheen's role in the 1974 TV movie The Story of Pretty Boy Floyd, which presents him as a family-oriented figure with a sense of justice, akin to a "Robin Hood of the Cookson Hills," prioritizing his appeal to over documented robberies. depicted him in the 1975 TV film , linking Floyd to the 1933 event despite later evidence exonerating him from direct involvement. Musical representations have further entrenched Floyd's folk-hero image. Woody Guthrie's 1939 ballad "Pretty Boy Floyd" sympathizes with him as an outlaw targeting exploitative banks—"some rob you with a six-gun, some rob you with a fountain pen"—reflecting Depression-era resentment toward financial institutions, and has been covered by artists including and . John Steinbeck alluded to Floyd in The Grapes of Wrath (1939) as a symbol of resistance against systemic poverty, amplifying his cultural resonance without endorsing criminality. Historiographical treatments contrast sharply with these portrayals, grounding Floyd in empirical records of his 30-plus bank robberies across , , and the Midwest from 1929 to 1934, including the confirmed killing of lawman Erv Kelley on April 9, 1932, near . Biographer Michael Wallis's Pretty Boy: The Life and Times of Charles Arthur Floyd (1998) contextualizes his crimes within tenant farming hardships and prison influences but rejects romanticization, detailing his progression from petty theft to armed holdups and FBI designation as " Number One" by in 1934, based on eyewitness accounts and federal files rather than folklore. Analyses debunk the "" myth of selective theft or mortgage-burning as unsubstantiated anecdotes propagated by admirers, noting instead indiscriminate targeting of deposits from ordinary depositors and associates' involvement in fatalities, such as the disputed , where Floyd's role was refuted by and alibis. While his October 28, 1934, funeral drew over 20,000 mourners—Oklahoma's largest—historians attribute this to economic alienation rather than evidence of benevolence, cautioning against conflating public sympathy with exoneration of violence. Federal archives and state records prioritize causal links between Floyd's actions and law enforcement escalations, portraying him as a product of opportunity in chaotic times but ultimately a perpetrator of felonies that exacerbated insecurity for rural communities.

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