Our Arklahoma Heritage: Depression-era outlaw lore includes 1927 bootlegging trial in Van Buren for Flossie Kimes
- Dennis McCaslin
- Aug 20
- 5 min read
In the sultry summer of 1927, the Van Buren courthouse in Crawford County hummed with anticipation. Flossie Kimes, a young woman barely out of her teens, stood before the judge, her name tied not only to charges of bootlegging but to the notorious outlaw George T. Kimes, her husband of less than a year.
The air was thick with the weight of Prohibition-era tensions, where the line between survival and crime blurred in the borderlands of Arkansas and Oklahoma. Flossie’s trial was no mere legal proceeding; it was a spectacle that drew crowds eager to witness the saga of a woman caught in the orbit of one of the region’s most infamous criminal families.
Her story, and that of George, was a tangled weave of rebellion, poverty, and a defiant legacy that would echo far beyond the hills of Crawford County.
George T. Kimes was born on February 29, 1904, in Van Buren, to Cornelius Kimes and Lillie Mae Poe. Raised in a working-class household, George grew up in a world where economic hardship was a constant companion. The early 20th century was a time of flux in the Arkansas-Oklahoma borderlands, where rural communities grappled with the shifting tides of industrialization and the crushing weight of poverty.
By the mid-1920s, George had turned to a life of crime, joining his older brother Matthew in a series of audacious heists that would cement their names in the annals of outlaw history.
Their exploits began with a bank robbery in Depew, Oklahoma, on June 30, 1926, a brazen act that set the stage for their rapid descent into infamy. Days later, they orchestrated a double bank robbery in Covington, a feat that showcased their growing boldness.
But it was in Sallisaw, during a deadly shootout, that their path took a darker turn. Deputy Perry Chuculate, a Cherokee lawman, was killed in the chaos, and George, still a young man of 22, found himself convicted of manslaughter, sentenced to 25 years in the Oklahoma State Penitentiary at McAlester.
Just weeks before his capture, George had married Flossie Fern Johnston on August 13, 1926, in Fayetteville. Flossie, born on September 16, 1909, in Okfuskee County, Oklahoma, to Noah Johnston and Nellie Esther Ralston, was only 16 at the time--a girl thrust into a tumultuous marriage with a man already on the run.
Their union was a fleeting moment of hope in a life otherwise marked by desperation. When George was arrested, Flossie was left alone, a young bride navigating a world that judged her not only for her husband’s crimes but for her own defiance of the law.
By July 1927, she stood trial in Van Buren, charged with manufacturing and selling liquor alongside W. P. Spradley Jr. and A. H. Dunn. The term “scofflaw,” freshly coined to describe those who flouted Prohibition’s strictures, fit Flossie perfectly.
Her trial drew a crowd, not just for the charges but for her connection to the Kimes–Terrill Gang, a name that sent shivers through the region. Newspapers buzzed with the story, noting the public’s fascination with this young woman who seemed to embody both victim and rebel in an era that demanded conformity.
The outcome of Flossie Kimes' trial in Van Buren is not explicitly detailed in available records. Historical accounts do not specify whether she was convicted or acquitted. Given the lack of definitive information in the sources, including newspaper clippings from the time that note the trial's significance but omit the verdict, it’s likely that the case did not result in significant legal consequence.
The Kimes–Terrill Gang, active in the mid-1920s, was a force of chaos across Oklahoma, Arkansas, and Kansas. Led by Matthew Kimes, with George as a key accomplice, the gang carved a path of destruction through bank robberies, jailbreaks, and violent confrontations.
Their audacity peaked in 1927 with a daring rescue of Matt from the Sallisaw jail, a move that humiliated law enforcement and emboldened their spree. They kidnapped a police chief during their flight to Arkansas, a bold act that underscored their disregard for authority.
Their final flourish came with a $207,000 robbery in McCune, Kansas, followed by a return to Beggs where they looted two banks in a single day. The Beggs robbery ended in tragedy, with Marshal W. J. McAnally killed by gang member Roy Brandon, a paralyzed driver armed with a shotgun.
The gang’s reign was short-lived but left a trail of bloodshed and fear, with George’s manslaughter conviction and Matt’s life sentence for murder marking the end of their run.Flossie’s role in this saga was less documented but no less compelling.
Her trial in Van Buren was a microcosm of the era’s contradictions--Prohibition had turned ordinary citizens into criminals, and women like Flossie, often driven by economic necessity, found themselves in the crosshairs of a moral crusade. Bootlegging was a common trade in the borderlands, where poverty made illegal liquor a lifeline for many families.
Flossie’s involvement, whether born of loyalty to George or her own survival instincts, painted her as both a participant in and a casualty of the Kimes family’s defiance. The courtroom, packed with onlookers, buzzed with whispers about her youth, her marriage, and the shadow of her husband’s crimes.
Yet Flossie was no mere footnote; she was a woman navigating a world that offered few options, her actions a testament to the resilience and rebellion that defined the era’s outcasts.
The Kimes family’s roots ran deep in Okmulgee County, Oklahoma, where their crimes often targeted familiar ground. Census records from the period reveal little about George’s mother, Lillie Mae Poe, but hint at a family bound by both community ties and a penchant for rebellion.
Prison records from McAlester, where George served his sentence, paint a picture of a man who, despite his crimes, was seen as redeemable. In 1945, Matt Kimes, a model prisoner for 18 years, was granted a controversial leave from the penitentiary, only to rob a bank in Morton, Texas, and die weeks later in Little Rock, struck by a poultry truck while fleeing a potential grocery store heist.
George, by contrast, survived his prison years, eventually settling in Sacramento, California, where he died in 1970. Flossie outlived them all, passing away in Redmond, Oregon, in 2001 at the age of 91, her life a quiet epilogue to a story that began in the crucible of the 1920s.
The Kimes saga is more than a chronicle of crime; it is a window into the cultural and economic pressures of the Prohibition era. In the borderlands of Arkansas and Oklahoma, where survival often meant bending the law, families like the Kimeses were shaped by the stark realities of poverty and the allure of defiance.
Flossie’s trial in Van Buren underscores the often-overlooked role of women in this history--not as passive bystanders but as active players in a world that demanded they choose between submission and rebellion.
The Kimes–Terrill Gang, with its bank heists and shootouts, fed into the myths of the American outlaw, a narrative that romanticized their lawlessness while ignoring the desperation that fueled it.
