In the Rearview: The Life and Times of OKC’s Most Notorious Bootlegger — Part 1

by Lynne Rostochil.  Photos from the Oklahoma History Center unless otherwise noted.

As you may know, I love a good true crime story, and when I learned about an Oklahoma City bootlegger named Lindsey Chambless, who operated in the Metro throughout the 1940s and 1950s, I decided to do a little Mod Blog post devoted to him and his activities.  Well, my research opened a Pandora’s Box filled with interesting characters and fascinating stories that turned my intended short article into a giant tome that uncovers more twists and turns than a meandering Oklahoma back road.  Over the next few weeks, you’ll learn all you ever wanted to know about Prohibition in the Sooner State and some of the people who made the time after World War II such a lively period in our history.


On a chilly, rainy November night in 1957, three lawmen made their way to the Rowland farm along the South Canadian River, not far from the Municipal (now Will Rogers) airport.  Oklahoma County Sheriff Bob Turner, Deputy Sheriff E.A. “Boots” Capshaw, and the head of the FBI in Oklahoma City, D.A. “Jelly” Bryce plodded through weeds and overgrowth and sloshed through mud to a large tree near the river bank.

That’s where an anonymous tipster may or may not have told them they could find the body of a long-missing bootlegger named Lindsey Chambless.

Sure enough, after they uncovered less than a foot of earth, the men came across the badly decomposed remains of a man still dressed in a brightly patterned shirt and casual slacks.  In the corpse’s pockets, the men found corroded nail clippers, a watch, two sets of keys, and several loose coins.

In the coming hours, the sky cleared and the site around the tree became a hub of activity as more investigators arrived, along with news-hungry reporters and photographers eager to get a juicy story for the next edition of the Oklahoman.  Amid the controlled chaos, the body, which was no more than a skeleton bound by disintegrating clothing, was removed to the Coroner’s office and the surrounding area was inspected for further clues.  Just before the sun began to rise to awaken the day, people began clearing out to interrogate witnesses and file stories, and once again, quiet claimed the landscape for itself.

Lindsey’s Early Years

Orval (sometimes known as Orville) Lindsey Chambless was born on January 30, 1916, near the flat, dusty West Texas town of Plainview, where his father, Hiram, had recently transplanted the family to work as a farm laborer.  Working in West Texas with no family around couldn’t have been easy, so soon after Lindsey was born, the family packed up and headed back home to the lush, rolling hills of East Texas in Red River County.  There, Hiram went to work on his parents’ farm while Lindsey’s mother, Edna May tended house and looked after Lindsey and his two older siblings, Van and Zelma. Sadly, just as they were settling into their new life, Edna May died at the age of 25, leaving two-year-old Lindsey and his brother and sister motherless.

Ten years later in 1928, 40-year-old Hiram married a young girl of 18 named Cordie.  She was just six years older than Lindsey, and Van and Zelma may have disliked this new living situation because when the family moved to Oklahoma City soon after the marriage, Lindsey’s siblings didn’t go along for the ride.  In the city, Hiram found work as a distiller for an oil refinery, and the couple with a teenaged Lindsey in tow moved frequently from one cheap flat in the southwest part of town to another.

A year after their marriage, Cordie gave birth to Hiram, Jr., but the celebration was short lived when, in 1930, Lindsey’s older brother, Van, died.  He was just 20 years old and left behind his 17-year-old wife, Verda, who was nine months pregnant, and a one-year-old daughter.  More sadness came when, after Cordie had a second child, she and Hiram called it quits.  Cordie moved to a farm in rural Oklahoma with her youngest child, but she left young Hiram with his dad.

Marriage number three seemed to be the charm for Hiram.  In 1933, he wed another young woman, 20-year-old Lula, who would go on to bear two children when Hiram was in his 60s.  Here’s the couple celebrating their 25th wedding anniversary in 1958:

At the time of Hiram’s third marriage, Lindsey was 17 and already proving to be quite a trouble maker.  In 1934, he was arrested for second-degree burglary and was sentenced to serve 14 months in the Oklahoma State Reformatory in Granite, which at the time only housed inmates under the age of 23.

The Reformatory, “Mother” Waters, and Escape

The Oklahoma State Reformatory opened in 1910:

When Lindsey arrived as an inmate in 1934, the place was run by Clara Waters, the first female warden in charge an all male prison in the U.S.

Waters was appointed to the position in 1927 after her husband, George, suddenly died while serving as warden.  The mother of eight, she ran the reformatory as an efficient, spic-and-span household, where “lewd pictures and suggestive inscriptions were ordered removed from the walls” and where inmates had to take off their hats in the presence of women, refrain from reading paperback novels, and use clean language.

Waters believed she could truly reform the young men in her care, so she created the first “fully accredited, behind-the-walls secondary school (Lakeside School) in the United States.”  She also started a popular boys’ band, invested in a library, and set up religious programs at the institution.  Here are photos of the band and the “Negro quartet”:

The matronly warden was always on hand to give her beloved “boys” motherly talks instead of harsh punishment.  When that didn’t work, the warden had some very interesting ways of punishing prisoners who got out of line.  Instead of confining them or beating them as was common in other institutions, Waters had them dress up in women’s clothing and paraded them in the Rotunda, where visitors and other inmates could laugh at and ridicule them.

Lindsey’s arrival coincided with a couple of interesting events at the reformatory.  First, while Waters had easily weathered two previous administrations, she was coming under unprecedented scrutiny by newly-elected governor, Ponca City oilman E.W. Marland, who took office January of 1935.

A former inmate had reported Waters for extreme cruelty, and Marland, who apparently had little respect for the female warden, was using that as an excuse to replace her.  Just as that was happening, the second event unfolded on February 17, 1935, when 31 inmates made a spectacular and bloody break from the reformatory.

According to the Oklahoman, armed with a couple of smuggled arms, two of the inmates threatened to shoot a guard if he didn’t turn over his keys.  He did and the inmates added to their ranks as they ran down halls “howling insanely.”  Then, “the mob of plotters ran upstairs in the administration building to the visitors’ room where 15 or 20 women and children” were waiting to visit loved ones.

The inmates used the women and children as human shields as they made their way through the reformatory to the entrance.  There, one of the armed escapees murdered a tower guard who was about to take aim at them while others scrambled into nearby two parked cars and made their getaway.  The rest of the gang made a desperate mad dash for the highway that ran next to the reformatory just as Clara Walters ordered her surviving tower guards to open fire on her once beloved boys.  This is where a lot of the fire came from:

“Slugs from … (the guards’ guns) … ripped into the flesh of eight convicts.”  They and two others were immediately captured, but the rest of the convicts made it to the road, hijacked unsuspecting drivers, and took off.   Eighteen young men were able to get away but most of them were quickly captured and returned to prison.

The three ringleaders of the break were the last of the bandits to be caught.  W.L. Baker, Jr., was an 18 year old serving 15 years for manslaughter, Dale Stamphill, 22, was at the reformatory after receiving 20 years for armed robbery, and 21-year-old Malloy Kuykendall was serving 75 years, also for armed robbery.  After breaking out, the three blazed a spectacular trail through rural Oklahoma and Texas that began when the trio robbed the Seiling First National Bank just 10 days after escaping from the reformatory in Granite.

Kuykendall injured his hip in the robbery, so the men tracked down and kidnapped the local doctor, Fred Myers, and forced him to treat the desperado’s wounds and drive them over the state line into Texas.  After they thought they were safe, they released the doctor, saying that his car was too slow and they needed a faster one.  But, for some reason, the not-so-bright boys didn’t get another car and instead hiked through fields and farms back into Oklahoma.

On Tuesday, March 5th, lawmen got a tip that the young men were hiding out in a ditch at the John Jester farm 15 miles west of Fairview.  A posse of over 100 men and an airplane scout descended on the farm and surrounded the escapees, who were hiding in an earthen dugout.  “Trapped in a hole like so many rats,” the three men emerged with guns a’blazing.  Kuykendall was shot and wounded by one of the officers, and the other two fugitives, seeing that there was no way out, quickly surrendered.  Here’s a photo of Stamphill, Kuykendall, and Baker soon after their capture:

All of the escapees were back in custody and several of them, including Kuykendall, Stamphill, and Baker, were tried and convicted for the murder of the prison guard and received life sentences to be served at the Oklahoma State Prison in McAlester.  In addition, the three ringleaders were brought up on federal charges for the bank robbery and kidnapping of Dr. Myers.  Once again, they were convicted and since they were known escapees, the men were sent to Alcatraz:

Here are Kuykendall’s orders to go to Alcatraz and his file there (photos here and of inmates from the Alcatraz archives):

I’m not sure what ended up happening to Baker, but Kuykendall, whose first arrest was for stealing chickens when he was a young teen, was now inmate #434 at “the Rock”.  Because he had two escapes to his credit (the first was when he broke out of a Tecumseh jail a few years prior to the reformatory incident), he was placed on 24-hour watch at his new home on the craggy island.  He would serve two stints at Alcatraz and time in Leavenworth…

… before being released in the early 1960s.  Now that he was older and wiser and a free man again, Kuydendall opted to live a quiet life and married and had children.  He died in 1967 at the age of 53.

Dale Stamphill became prisoner #436 at Alcatraz:

The restless young man didn’t like being locked up and even though he, too, was closely monitored at Alcatraz, the criminal with more gumption than brains attempted another brazen escape in 1939.  In the middle of the night on January 13th, Stamphill…

… and four of his buddies, Arthur “Doc” Barker (son of the notorious Ma Barker),

William Martin,

Rufus McCain,

and Henri Young…

… used saws and benders to open up the window bars in the supposedly secure D Block isolation unit.  The five men pulled themselves through the windows and ran through the chilly night to the water, where they gathered wood to construct a makeshift raft.

Suddenly, the prison siren blared and tower lights searched back and forth before resting on the men, who were in their underwear by this time because they had been using their clothing to tie the wood pieces together.  Shivering in the brutal cold on the shore, Martin, McCain, and Young immediately surrendered, while Barker and Stamphill still thought they could make a getaway if they just put a few more pieces of the raft together.

A series of shots pierced the quiet night.  “Doc” Barker was shot in the head and lay mortally wounded, and Stamphill was wounded in both legs.  One bullet nicked an artery, nearly killing the Oklahoman, and he survived only to be placed, along with his fellow escapees, in solitary confinement for 22 months.  (Read a much more detailed version of the prison break here.)

After the wannabe escapees’ release back into the general prison population in 1941, Young killed McCain by plunging a spoon handle into the man’s neck.  Young’s story and the resulting trial were the basis of the 1995 movie, “Murder in the First.”  Stamfield remained in prison for at least another 25 years, but he was ultimately released, got married, and lived out the rest of his days in Kansas, where he died in 1998.

As for Clara Waters, the reformatory break out back in Granite was the last straw for her nemesis, Governor Marland, and his cohorts, one of whom stated, “… there is a bad moral condition out there (at the reformatory).  A woman just can’t manage it.”  She was removed from her position of eight years the day after the breakout and replaced with a man, who I’m sure did a much better job … at least in the eyes of Marland.

She didn’t let that setback stop her, though.  Not at all.  In fact, this trailblazer ended up serving at the vice-chair of the state’s Democratic Party and was tapped by Franklin Roosevelt to head the Oklahoma women’s program of the National Youth Administration.  She lived to the ripe old age of 89 and died in Stillwater in 1977.

Perhaps because he was due to be released in a few months, anyway, Lindsey Chambless didn’t participate in the reformatory escape.  In fact, he uncharacteristically stayed out of trouble during his stay under Mrs. Waters’ care and was released later in 1935.  Unfortunately, her motherly talks didn’t make much of an impact on Lindsey.  Perhaps he enjoyed dressing up in women’s clothes or maybe he just liked the thrill of living on the edge; either way, he was soon committing crimes again, which landed him in federal prison for two stints in the late 1930s and early 1940s.

Lindsey Becomes the “Flying Bootlegger”

By 1947, Lindsey was 31 and one of the best known bootleggers in Oklahoma City.

The Sooner State had been dry ever since statehood in 1907 when prohibition was included in its constitution.  Even after national prohibition was repealed in 1933, Oklahoma remained mostly dry – the only exception was a law passed the same year that legalized low-point beer because it was deemed non-intoxicating.

From 1936 to 1949, Oklahomans voted three times to repeal prohibition, and it failed each and every time.  According to the Oklahoman, that didn’t mean that the state was comprised mostly of teetotalers.  On the contrary, “the referendums may not have accurately reflected Oklahomans’ views on the issue.  Because liquor was not regulated by the state, drinkers could buy smuggled alcohol cheap and were not excited about paying state taxes.  As long as they could get their alcohol, Oklahomans had little problem with the law.”

With so many eager buyers on hand, bootlegging was quite a profitable business, and citizens from every socio-economic background had their favorite bootlegger, who could easily supply bourbon, whiskey, or any other spirit and surreptitiously deliver it to their door … their back door, of course.  Here’s a bootlegger’s card I found at a flea market a few years back:

Lindsey and his adventurous cohorts made all kinds of money during the celebratory and carefree days after World War II, and while they may be raided on occasion…

… for the most part, luck was on their side.  For example, Lindsey was one of the first to use planes to smuggle in his contraband from surrounding wet states, which earned him the title of the “Flying Bootlegger.”  In September 1948, according to a 2008 Oklahoma Today article,

Oklahoma County officers got a tip that a plane carrying whiskey was flying into Tulakes Airport in Bethany.  The local police and two Oklahoma Highway Patrolmen positioned themselves at the airport to make a bust.  Chambless arrived to wait for the plane, along with an accomplice, William Jefferson Hutto.  According to police, Chambless learned of the stakeout by listening to the Highway Patrol wavelength on his radio and ran onto the airfield to wave the plane off.  Bethany policeman Chester Longacre and his twin brother, Lester, a Nichols Hills constable, were hiding inside a hangar almost a mile away and attempted to block the plane’s takeoff with their car.  As they raced onto the runway, the plane took flight and escaped, narrowly missing the top of the Longacres’ vehicle.  Police only were able to charge Chambless with driving without proper license tags.

Lindsey was likely very happy to escape this incident with such a light charge because he was already in trouble for a much more serious crime – murder.


Next time, Lindsey is accused of murdering his lover’s husband and she has a pretty sad history with men.  Go here to read Part 2.