They weren't your typical Wild West desperados. Honestly, when you think of outlaws in the 1890s, you probably picture grizzled men with tobacco-stained beards and a chip on their shoulder. You don't usually think of two teenage girls from respectable-ish families. But Cattle Annie and Little Britches weren't interested in being respectable. They wanted adventure, and they found it in the dust and gunsmoke of the Oklahoma Territory.
Anna Emmaline McDoulet and Jennie Stevens. That’s who they really were. Before they became the legends known as Cattle Annie and Little Britches, they were just kids living in a hard, unforgiving landscape. Anna was barely 13. Jennie was maybe 15. By the time they were caught, they’d cemented a legacy that outlived almost every other member of the Doolin-Dalton gang.
It wasn’t just a phase. It was a lifestyle choice that blurred the lines between teenage rebellion and genuine criminal intent.
How Two Teenage Girls Joined the Doolin-Dalton Gang
It started with dime novels. You’ve seen the type—cheap, sensationalized stories about Ned Buntline heroes and noble bandits. Anna and Jennie devoured them. Living in the Cimarron Strip, they saw the real thing, too. The Bill Doolin gang used to hang around the local ranches, and to a couple of bored girls, these guys looked like rockstars.
They didn't just watch from the sidelines.
They started small. They'd swipe clothes, food, or whiskey for the outlaws. They acted as scouts. Because they were girls, the U.S. Marshals didn't pay them much mind at first. That was a mistake. Soon, Cattle Annie and Little Britches were stealing horses and selling "white mule" (illegal whiskey) to the Osage and Pawnee. They were fast, they were loud, and they could outride most men twice their age.
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Breaking Down the Personas
Anna McDoulet became Cattle Annie. She was the strategist, the one who saw the bigger picture. She was bold, but Jennie Stevens—Little Britches—was the firebrand. Jennie reportedly wore men's clothes and rode astride, which was a massive scandal back then. Most women used side-saddles. Not Jennie. She wanted to be able to gallop at a moment's notice.
There’s a common misconception that they were just "groupies." That’s not quite right. While they definitely admired the Bill Doolin crew, they were active participants in the chaos of the 1890s. They provided intelligence that kept the gang one step ahead of the law for months.
The Chaotic Arrest That Ended the Run
The law finally caught up in 1895. It wasn't some grand, cinematic standoff at high noon. It was messy.
U.S. Marshals Bill Tilghman and Steve Burke tracked them down near Pawnee. Annie was caught first. She tried to scramble out of a window, but Burke grabbed her. She didn't go quietly. Reports from the time say she cussed him out with a vocabulary that would make a sailor blush.
Jennie? She was a different story.
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When Tilghman cornered Little Britches, she didn't surrender. She fought. She clawed, bit, and even tried to go for her Winchester. Tilghman, who was a legendary lawman, actually had to spank her to get her to settle down—a detail that sounds bizarre today but was reported as a "disciplinary measure" at the time. They were kids, after all.
They were eventually taken to Guthrie, Oklahoma. The press went wild. People couldn't get enough of these "girl bandits." They were sent to a reformatory in Framingham, Massachusetts. It was a long way from the plains of Oklahoma.
Life After the Outlaw Trail: What Really Happened?
Most people think the story ends with them rotting in a cell. It doesn't.
Anna (Cattle Annie) served her time and eventually moved to Oklahoma City. She got married. Twice, actually. She lived a relatively quiet, law-abiding life until 1978. Think about that. A woman who rode with the Doolin-Dalton gang lived long enough to see the moon landing. She rarely spoke about her past, perhaps because the "Cattle Annie" persona was a shadow she wanted to leave behind.
Jennie's path was shorter. She was released earlier due to poor health. Some records suggest she did some social work or became a seamstress, but she died young, likely from consumption (tuberculosis) shortly after her release. The wild life took its toll.
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Why Do We Still Care?
We love a good underdog story, even when the underdogs are technically the "bad guys." Cattle Annie and Little Britches represented a specific kind of American defiance. They were young women in a society that gave them zero agency, so they took it by force.
Their story has been romanticized, most notably in the 1981 film Cattle Annie and Little Britches starring Amanda Plummer and Diane Lane. It’s a fun movie, but it definitely paints a glossier picture than the gritty reality of sleeping in dirt and dodging federal bullets.
Common Misconceptions About the Duo
- They were romantic partners with the outlaws: There’s no solid historical evidence of specific "boyfriend-girlfriend" relationships. It was more about the thrill and the lifestyle.
- They killed people: While they were armed and dangerous, there are no confirmed reports of either girl actually killing anyone during their spree.
- They were poor orphans: They actually came from families that were struggling but present. Their rebellion was a choice, not necessarily a survival tactic.
Actionable Steps for Western History Buffs
If you're looking to dig deeper into the actual history of the Oklahoma Territory outlaws, don't just rely on movies. The truth is usually in the archives.
- Visit the Oklahoma Territorial Museum: Located in Guthrie, this museum holds actual artifacts and records from the era when Annie and Jennie were active. It gives you a sense of the physical scale of their world.
- Read "The 101 Ranch" by Ellsworth Collings: This provides a broader context of the region during the transition from the Wild West to statehood.
- Check the Federal Bureau of Prisons Archives: You can find digital records of the Framingham Reformatory that detail the girls' time in custody, which offers a stark contrast to their "bandit" years.
- Explore the Bill Doolin Files: To understand why these girls were so enamored with the gang, you have to understand the gang itself. Researching the Battle of Ingalls is a great place to start.
The story of Cattle Annie and Little Britches isn't just a footnote in history. It's a reminder that the "Wild West" was populated by real, messy people—including teenage girls who just didn't want to do what they were told. They chose the saddle over the parlor, and in doing so, they ensured no one would ever forget their names.