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The story of Sherborn’s famous outlaw

By Amelia Tarallo
Hometown Weekly Special Correspondent

The stories of the old west have captured the interest of Americans for years. Some of us grew up watching “Little House on the Prairie.” Others watched the Clint Eastwood classics. The stories of cowboys and criminals have been a fascination for decades. These stories usually take place in the West.

The story arc of Cattle Annie’s life, however, brought her right through Sherborn, Massachusetts.

When Anna Emmaline McDoulet was born, her parents had no idea that she would become a notorious gun-slinging criminal. She was born in Kansas in 1882 and was one of nine children. Her father, ironically, was Judge James C. McDoulet. Before she turned to crime, Annie McDoulet worked as a dishwasher to earn money.

She was a perfectly normal child. That is, until her family moved to Skiatook, Oklahoma. There, McDoulet met the Doolin gang. McDoulet had been enchanted by the idea of cowboys and criminals, reading stories about them in newspapers. To her, meeting the Doolin gang back then was the equivalent of a teenage girl meeting Taylor Swift today.

Soon, Annie, along with her new friend, Jennie Stevens (sometimes written as Stevensen), became groupies of the dangerous Doolin gang.

Jennie was born in Oklahoma in 1879. She grew up reading and hearing the same stories that fascinated McDoulet. The two became fast friends. Stevens decided to go by the nickname “Little Britches” during her time as a criminal. The Doolin gang were infamous for robbing trains and banks, stealing horses, and weapons.

From there, McDoulet, who choose the outlaw name “Cattle Annie,” was on the path to becoming the sidekick of one of the most notorious gangs of the Wild West.

Details on the exact crimes committed by McDoulet and Stevens are a bit murky. Some rumors noted that they were involved in murders and train robberies. However, according to records, the girls committed minor crimes, like bootlegging. However, her arrest seemed to be a perfect example of the Wild West. The two were hunted down by a deputy marshal and a couple of other police officers. The two girls refused arrest and tried to kill the officers, committing to a shoot-out. The two outlaws eventually realized that they were outnumbered and gave up.

Following her arrest, McDoulet was sent to serve her prison sentence across the country in Framingham, Massachusetts, separating her from the place where she had once lived a life of crime.

MCDoulet made a new life for herself, moving to Sherborn. She worked as a maid or a servant for Mary Daniels. It is not clear whether or not Daniels knew about McDoulet’s past.

McDoulet did find her way back to Oklahoma, but she stayed far from crime. Sources say that she became a bookkeeper and married Earl Frost, with whom she had two children. According to records, Frost and McDoulet divorced in 1909. Shortly after, she joined a Wild West show, playing her role perfectly because of her experiences.

McDoulet died November 7, 1978, but her legacy lived. In her elder years, she was known to be a church-going woman, a responsible member of society. Her youthful years, however, have been portrayed in movies and books, just like the ones she used to read as a child.

But today we know just how unglamorous the life of an outlaw can be.

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