You Can’t Win · Chapter
Chapter XV explained
Jack Black recounts his time in Chicago, where he encounters the seedy underworld of bars, hop joints, and street girls.
What happens
Jack Black recounts his time in Chicago, where he encounters the seedy underworld of bars, hop joints, and street girls. He helps a desperate prostitute, Irish Annie, dispose of a dead man's body, only to be later betrayed by her in court. The narrative shifts to his apprenticeship with George, learning the trade of safe-cracking in Butte and other towns. They operate methodically, avoiding cities and living on the road. George's strict code against murder is emphasized, and Black reflects on the dangers of their life. In Salt Lake City, they establish a base, and Black learns of a potential easy score from a crippled beggar, which he and George plan to exploit.
Themes in this chapter
Underworld Code and Loyalty
George enforces a strict code against murder, emphasizing that their business does not include killing. He advises using a gun only to scare, not to hit, and warns against letting the gun become a master.
Survival and Adaptability
Jack and George constantly adapt to their environment, moving between states, living on the road, and planning heists with careful reconnaissance. They avoid cities and use the wilderness to evade capture.
Criminal Identity and Rehabilitation
Jack reflects on the life of a thief as a trade, with George never speaking of quitting. The crippled beggar, once a capable thief, turned to begging after losing a leg, illustrating the difficulty of leaving the criminal life.
Characters to notice
- George
Jack's mentor in safe-cracking; a methodical thief who abhors murder and enforces a strict code. He is past fifty and shows no desire to quit his trade.
- Irish Annie
A street girl Jack helps after a man dies in her room. She later perjures him into prison.
- Mary
Helps Jack and George after their arrest in Pocatello by arranging a fix with the judge. She later writes about the Sanctimonious Kid's arrest.
- Blacky
Montana Blacky, a bum found raving mad after the convention in Pocatello; his ravings may have led to Jack and George's arrest.
- Gold Tooth
Mentioned as the man George shot; the reason for the shooting is later learned by Jack after George's death.
- The Sanctimonious Kid
Arrested in Denver for a tough burglary; Jack and George help him by hiring a lawyer.
Key passages
“I put the dead man’s hat in my pocket and asked her to help me lift him to my shoulder. She refused to touch “the thing.” With an effort I got it to my shoulder, the head and arms hanging down my back. Clasping my arms around its legs, I staggered out the back way toward the alley.”
Jack carries the dead man's body out to the alley after Irish Annie refuses to help.
Illustrates Jack's willingness to help despite the danger and his growing unease with the situation.
“I felt sure she had dealt the man a jolt of chloral or some other stupefying drug.”
Jack suspects Irish Annie drugged the man, leading to his death.
Highlights the treacherous nature of the underworld and Jack's suspicion.
“George, although past fifty, never spoke of quitting. I doubt if the thought ever entered his mind. He was as much attached to his trade as any carpenter or bricklayer, and went about it as methodically as any mechanic.”
George is completely devoted to his life as a thief, treating it like any other profession.
Emphasizes the theme of criminal identity and the normalization of a life of crime.
““I’ve packed a gun for thirty years, and every time I fired it I was in the wrong except, maybe, when I let that Gold Tooth have it. That’s because my business is wrong. But it don’t include murder and I won’t travel with anybody that deliberately shoots people.””
George explains his code: he has used his gun only when necessary, but he refuses to associate with those who commit murder.
Central to the theme of underworld code and loyalty, showing George's moral boundaries.
