Cattle Annie & Little Britches

In the days of Bill Doolin and his “Wild Bunch” gang of outlaws, lawmen were also trying to put a stop to the message carriers who would warn the gang members when John Law (euphemism for law enforcement) was in the vicinity. With gang members constantly being warned, lawmen were mostly running wild goose chases, and it made them especially grouchy. In and around Pawnee and Perry, Oklahoma, two of these spies were also wanted for selling liquor to the Indians and for horse theiving. Both were sharp-shooters with either pistol or rifle, and in spite of their youth, or perhaps because of it, they managed to elude the not so long arm of the law consistently. It’s tough to imagine very young girls on the wrong side of the law, but the truth is that when it comes to female outlaws in the Olde West, none compare to the two teenagers from the Cherokee Nation of Oklahoma – “Cattle Annie”, and “Little Britches”.

Born Anna Emmaline McDoulet in 1879 to James C. and Rebekah McDoulet of Lawrence County, Kansas, Cattle Annie, one of eight children. When she was four years old, the family moved south to Coyville, Kansas. To help make ends meet, Annie went to work as a dishwasher in a hotel, and also did odd work wherever she could find it. At around age 12, the family moved to the Otoe Reservation near Skiatook, just north of Tulsa. It was here that her outlaw exploits apparently began. Jennie Stevens was born in 1879 to Daniel and Lucy Stevenson of Barton County, Missouri. The first eight years of her life were spent in Missouri. In 1887 or thereabouts, they moved west to Seneca on the Missouri border, the outer fringes of Indian Territory, where they lived for one year before moving further west into the Creek Nation at Sinnett in the southeast corner of Pawnee County.

Little Jennie apparently became mesmerized with the stories she heard of the notorious Doolin Gang when she was barely fifteen-years-old. Legend has it that donned men’s clothing and ran off to join the gang. On her first night out as an outlaw, she lost her horse and ended up being dropped at a neighbor’s by gang members. She had no choice but to slink on back home to her angry father who gave her a sound thrashing. She also was mocked by her little friends over the misadventure. These humiliations caused her to run away again and hook up with a deaf-mute horse dealer named Benjamin Midkiff, whom she married in Newkirk on 5 March 1895. They set up housekeeping in a hotel in Perry. Six weeks later, after discovering she was “entertaining” men while he was gone off horse-trading, Midkiff returned her in shame to her father. Nearly the very next day she started her outlaw rides up and down the Arkansas River.

At around sixteen, Jennie was reported to have married Robert Stephens, whom she left after six months. Whatever her marital relationships, she went to prison as Jennie Midkiff and into history as Jennie Stevens, the infamous “Little Britches” Back in the days of the Olde West, it was the custom in those days to hold country dances, and people would come from miles around to attend the much-welcomed break in hard work and hard times to celebrate. Attendees would naturally include the local outlaws. It was at one of these dances that Annie and Jennie, having formed a friendship as “neighbors”, they met members of the Doolin Gang, self-named the “Wild Bunch”. The Wild Bunch had a hideout in the Creek Nation Cave on the Cimarron River, not too far from Ingalls, a small town east of Stillwater, which would become infamous in 1893 for a gang shootout which would leave three marshals dead. Annie had gone to the dance with a local boyfriend, and he introduced her to George “Red Buck” Waightman. Naturally, as with many young and impressionable girls of any time, when Annie learned that her new acquaintance was a member of Doolin’s notorious Wild Bunch, she fell madly in love with him on the spot. We can imagine how larger-than-life and attractive this older wanted man was to the young and impressionable farm girl.
And so it was exciting time for the girls. And, rather than wait around for dashing outlaws to drop by the family spread, the girls decided to begin their own career of outlawry. According to one newspaper account, “…not only did they dare to wear men’s pants in the sanctimonious but scarlet nineties, but rode horses as men rode them, astride, and with heavy forty-fives swinging at their hips”

Both teenagers thrived in outlawry. By dressing in men’s clothing, they could confuse the sheriff posses, and with bandits for buddies, they quickly learned how to ride and shoot with the best of them. Throughout 1895, they made newspaper headlines throughout the Twin Territories. Their primary business was peddling whiskey in the Osage and Pawnee Indians, along with a pretty good sideline business of horse theft. They kept their eyes and ears open for gang members’ concerns, too. They struck at odd times, mostly at night, sometimes together, and sometimes alone, and confused law enforcement handily. Once in eastern Payne County, a posse met Cattle Annie on the trail. Questioned about the “passing of strange men,” the girl gave evasive and unsatisfactory answers, but her identity was not known, and she was let go. She immediately sent a message to the Doolin Gang’s hiding place that the law was near, and the outlaws evaporated.

In mid-August 1895, Jennie was arrested. It was a Sunday evening and Sheriff Frank Lake took her to a restaurant in Pawnee for supper, and a guard was placed at the door. Newspaper reports of the next day had a field day mocking law enforcement, reporting that after Jennie finished eating, she darted out the back door, ripped of her dress, seized a horse and ran off into the night. Several officers chased her, but she escaped, and the papers gleefully told of of Jennie riding out “…on the horse [stolen] from a deputy marshal [Frank M. Canton] who had arrested her for selling whiskey to the Indians.”

The following night, Annie and Jennie were tracked down and found near Pawnee by Marshals Bill Tilghman and Steve Burke. Burke remained outside, while Tilghman charged inside. Both girls gave fight, and several shots rang out, as the girls made their way to a back window to escape. Cattle Annie was caught by Burke, as she climbed out the window, and was wrestled to the ground, but Little Britches escaped and gave a long chase. She fired over her shoulder at them, only her aim was not good, and her shots missed. Tilghman finally shot her horse, and horse and rider crashed to the ground. Although she fought wildly, Jennie was finally taken into custody, and both girls were taken to jail.

Annie and Jennie were tried before Judge Andrew G. Curtain Bierer of the Fourth Judicial District of Oklahoma Territory charges of stealing horses and peddling spirits to the Indians. Annie got one-year sentence, and was sent the Framingham reformatory for women in Massachusetts in 1895. She was paroled a few months later, due to poor health. She refused to go home, saying she would return to her life of crime, and remained at Framingham until she could find work as a domestic. In 1898, she went to work for Mrs. Mary Daniels in Sherborn, just south of Framingham. A few months later, she went on to New York, where some stories claim she died of consumption in Bellevue Hospital. Other stories claim Annie went back to Oklahoma and married Earl Frost of Perry in 1901, had two children, and divorced in 1909. Information in the museum in Guthrie, Oklahoma claims she married a second time to J. W. Roach of Oklahoma City and died in 1978. Another tale, which has become legend, has her returning to Oklahoma, marrying twice before marrying Jack Dalton and settling down to life in Purcell as Anna Ohme Burke Dalton. The truth may never be known. “Little Britches” Jennie was held for two months in the Guthrie jail, the territorial capital of Oklahoma, as a material witness in a murder trial. She had been working as a domestic in a home where she had witnessed one man shoot another. Her two-year prison sentence began in Framingham reformatory in Massachusetts in 1895, and she was released in October 1896 for good behavior. She returned to her parents in Sinnett, Oklahoma Territory. What finally happened to Jennie is a mystery. There are a variety of stories that claim she married, settled down, and raised a family, living an exemplary life in Tulsa, but none of these stories ever gives any times, places, or names.

Cattle Annie and Little Britches lived the outlaw life for just two short years. But their frantic, wild and daring criminal exploits gave marshals and peace officers in the Twin Territories absolute fits. Who would believe that two young girls could cause so much havoc? And then they quietly disappear. Did they learn their lesson and settle down and live exemplary and long lives, putting their outlaw past behind them as some have said? No one really knows. And no one knows how many women have claimed to be Cattle Annie or Little Britches, telling tall tales to family and friends in hushed conversations, attaching themselves to the colorful legends so they’d be treated more kindly and with more respect. And that brings us to another ponder: Was all this at baseline just two young girls looking at long lives of servitude and back-breaking work that made them seek out independence, freedom and their own money—a situation that was truly not available to women in the Olde West? When we look at the legends of female “outlaws”, the thread of poverty, want, despair, and “choices” that were only a choice between terrible circumstances and less terrible circumstances is very evident. Life was hard in the Olde West, and especially for young girls and women.

Main source for background information: Lee Paul -


Outlaw Ladies Pictures

  • Portrait of Two Outlaw Ladies - Most probably Photoshopped - No pictures of Cattle Annie & Little Britches exist

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