01 - Boyhood and Early Crime

·21 min·2 clips

At six years old, James was convinced by older boys to steal from his brother's grocery store till.

This episode is the first chapter of an autobiographical account narrated by a professional thief reflecting on his early life. The narrator, born in 1868 in New York City, recounts his childhood and initial descent into crime with complete frankness. He describes his family as poor but honest, with a father who worked for Brown Brothers and Company. His first theft occurred at age six when older boys convinced him to steal eight or ten dollars from his brother's grocery store till. These older boys, including an eighteen-year-old ship caulker and a seventeen-year-old roustabout, rewarded him with trips to theaters like Tony Pastor's and rowboating. After being caught and beaten by his father, he continued stealing from family members, partly for theater money and partly for excitement. At eight, he participated in stealing a box of valuable jewelry from a visitor but received none of the proceeds from its sale. A subsequent theft of a box from a wagon yielded only a decorative sword, which he felt was unfairly traded for a minimal payment. He recalls a violent incident where, after a friend stabbed him in the leg with a penknife, he nearly severed the boy's ear with a hatchet. His brief time in parochial school ended after he insulted a teacher and was blamed for various mischiefs, while a pious classmate later went to prison for robbery. The narrator developed a fascination with old buildings, theaters, and history, contrasting with his skepticism toward religious ceremonies. He was a bright student in public school but played truant constantly, holding contempt for his virtuous family. A pivotal moment was his family's move to Cherry Street, near a saloon that was the headquarters of the professional "Old Border Gang." Seeing these well-dressed, successful thieves formed his ambition to pursue a life of graft. He began pilfering more seriously, stealing items like silver plates, shoes, and dresses to pawn for money. At about thirteen, he and his friend Zach witnessed a pickpocket in action on a streetcar and received a share of the stolen money. This inspired them to attempt their first pocket-picking, successfully stealing a handkerchief containing ten dollars from a woman. The pickpocket they had originally observed later acknowledged their achievement and gave them private lessons, making them feel they were rising in the criminal world. The narrator contrasts his current shattered health and nerves with the simple happiness of his brother, a truckman with a modest salary. He reflects that his impulsive nature and early arrogance led him to believe the world owed him a living. The tone is confessional and reflective, blending vivid storytelling with candid introspection about a life gone astray. The style is narrative and descriptive, offering a raw, firsthand look at 19th-century New York's underworld and a child's socialization into crime. Listeners interested in historical crime memoirs, social history, or psychological portraits of criminality would find this episode compelling. Those seeking a lighthearted story or a formal historical analysis might find its gritty, personal narrative less engaging.

As heard by us

A thief's boyhood story, told with unusual candor and little interest in self excuse.

James's first chapter is plainspoken and a little uneasy in the best way. It follows a boy on the east side of New York as he shifts from favored child to skeptic, then to school troublemaker, and finally to a boy reaching for money that is not his.

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Why you'd press play

Press play when you want a boyhood theft story told in a frank first-person voice by a man who says he will tell the truth about how he became a crook.

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