Bill Caldwell: Teenagers Cattle Annie and Little Britches broke outlaw stereotypes in 1890s

Jul 21, 2023

Dime novels published after the Civil War gave fictional accounts of the lives of real people. Readers “knew” exactly what outlaws were like and the exciting lives they led. However, none of the dime novelists made heroines of teenage girls becoming outlaws.

For Anna McDoulet and Jennie Stevenson, known as Cattle Annie and Little Britches, their two-year career as outlaws was a tale stranger than fiction.

Jennie Stevenson was born in 1879 to Daniel and Lucy Stevenson on a farm in Barton County, Missouri. She was the younger of their two daughters. Around 1887, the family moved south to Seneca in Newton County. They were farmers, poor and uneducated, though respectable. They stayed in Seneca for a year before moving to Sinnett in the Creek Nation in Indian Territory, west of Sand Springs.

Anna McDoulet was born to James and Rebekah McDoulet on Nov. 29, 1882, in Lawrence, Kansas. She was one of eight children. James McDoulet was a lawyer and preacher. The family moved to Coyville in Southeast Kansas in 1886. When Anna McDoulet was 12 in 1894, they moved to Skiatook, north of Tulsa. She was large for her age and hired out as a domestic servant and dishwasher.

All through the 1880s, reports of the Dalton and Doolin gangs roaming the area were common knowledge throughout the territory. Romanticized tales of outlaw life entranced both girls.

When Stevenson was almost 15, she decided farm life was not for her. She took a suit of men’s clothing, one of her father’s horses and left to join the Doolin gang. Both Stevenson and McDoulet knew how to ride and could handle hand guns and rifles.

Stevenson didn’t get far. On her very first night, she lost her horse and gang members unceremoniously dropped her off at a neighbor’s place. She arrived home only to get a thrashing from her father. To add insult to injury, her friends mocked her failure.

The shame of failure stirred her to run away again. This time she took a different tack. She met a deaf-mute horse trader named Benjamin Midkiff. They married March 5, 1895, and lived in a hotel in Perry, Oklahoma, about 50 miles west of her parents’ place.

It wasn’t long before Midkiff discovered that while he was away, she was allowing men to “visit her room.” They moved east 50 miles to Osage City to make a new start, which did not change her habits. Frustrated, Midkiff took her back to her father’s home. One account reported that “almost the next day, she started her dishonorable rides up and down the Arkansas River, keeping the lowest company.” When Midkiff found her in Cleveland, Oklahoma, staying in a store with two young men, that settled it. On the way back to her parents, they “fell out and quit on the road.”

To spite him, she, now 16, married Robert Stephens. It lasted just six months. In the meantime, she met a neighbor girl three years her junior — Anna McDoulet. The exact circumstances of their acquaintance are unclear. But local dances were big events at the time. They probably met Doolin gang members at local dances. The gang members were young men and often attended the dances. McDoulet met and fell for Buck Waightman, one of the Doolin gang. She “started out on a career of romance and bullet diet.” She became known as Cattle Annie.

The girls decided they could be outlaws just as well as men. While they had ties with Waightman and his gang, they had their own operations going. They peddled whiskey to the Osage and Pawnee, stole horses when the opportunity arose and passed along news of “John Law,” which the gang welcomed. The gang nicknamed Stevenson, the smaller of the two, “Little Britches.” Once Cattle Annie happened to meet a posse on the trail. When questioned about “strange men,” she was evasive but was let go on her way. In the clear, she notified the gang who scattered and escaped.

They became celebrities in their own right in territorial papers. In one 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.”

The two had been arrested in early 1895 for peddling whiskey to Indians and stealing horses. The first time they posted bond and continued their business. Not long after that they were arrested twice but escaped from jail.

Stevenson was helped in her escape by Frank Wilson, a “rounder from Pawnee.” He sold whiskey to the Osage. She joined his bootleg operation. She did domestic work by day and then changed to men’s apparel and posed as a tramp to sell whiskey to the Osage at night. This worked for six months until she and Wilson were arrested in June 1895.

She was sentenced to six months in the federal jail in Guthrie, Oklahoma, on July 5. However, she escaped jail and found McDoulet. Their whiskey peddling only lasted another month until a four-man posse located them Aug. 18. Stevenson was arrested by Sheriff Lake near Pawnee. That evening, he stopped in Pawnee to eat at a restaurant. He posted a guard at the front door. Stevenson bolted out the back door, stripped off her dress, mounted the lawman’s horse and fled into the night. Despite shots in her direction, she escaped unharmed. She joined McDoulet at the ranch where McDoulet had been hiding. Newspapers mocked the sheriff’s failure.

On Aug. 25, the girls were discovered at the ranch. They put up a fight and shots were fired before surrendering. After their arrest, they complained that “if they had known there were only four officers surrounding them, they would have fought their way out.”

Newspapers reported the Department of Justice was somewhat perplexed at how to deal with the teenage girls. While officials considered their options, a reporter was allowed to talk with them. McDoulet said she was “past redemption” and would return to crime when released. He described her as “large for her age, but possesses a pretty face, something the Midkiff girl cannot boast of.” Whereas, “the Midkiff girl sits in the federal jail and sulks and is afraid to look into a mirror for fear of cracking it.” A newspaper said Stevenson was “a splendid sample of the new woman in a depraved line.”

McDoulet was committed to reform school in South Farmington, Massachusetts, and left on Sept. 5. Stevenson had to stay to testify as a witness in the Patsy Alred murder trial. Jennie was convicted of horse stealing and sentenced to two years in the Massachusetts Reformatory prison in Sherborn.

McDoulet was paroled just a few months into her one-year sentence due to poor health. Two stories circulated about her fate. One said she refused to return to Oklahoma lest she go back to crime. Instead, she worked as a domestic in Massachussets and later New York, where it is said she died of consumption, or tuberculosis. In the other story, she eventually returned to Oklahoma, married, had two children, then divorced. She married J.W. Roach and lived quietly until her death at age 94.

Stevenson entered the reformatory in November 1895. She was released in October 1896 for good behavior. She returned to her parents in Sinnett and disappeared from history.

Their story was the basis for the 1980 film, “Cattle Annie and Little Britches.” It starred Amanda Plummer, Diane Lane and Burt Lancaster. Almost as romanticized as dime novels, it bore only tenuous ties to their real lives.

After falling in love with romanticized tales of outlaw life, the girls learned over their two-year crime spree it was not that romantic. Gangs fell apart due to deaths, internal strife or arrests. Yet they proved to be just as adept as men at crime. But life on the run could not sustain the allure dime novels held out and both women chose the path of reformation upon release.

Bill Caldwell is the retired librarian at The Joplin Globe. If you have a question you’d like him to research, send an email to [email protected] or leave a message at 417-627-7261.

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