# XXIII explained — You Can’t Win

> Chapter companion for You Can’t Win by Jack Black.

## What happens

Jack Black recounts his time in county jail, his hatred for Irish Annie and her eventual death, his transfer to Folsom prison under Captain Murphy, his long stay at Ingleside jail during the graft prosecution, and his eventual escape with the help of a friend. He also describes his meeting with Fremont Older and his struggle to quit opium.

## Themes in this chapter

### Criminal Identity and Rehabilitation

Jack Black reflects on his criminal past, his attempts to quit opium, and his promise to Fremont Older to stop stealing.

### Underworld Code and Loyalty

Jack Black discusses the substitute for honor among thieves and the loyalty of his friend who helped him escape.

### Addiction and Self-Destruction

Jack Black describes his opium addiction and the physical toll it takes on him, as well as his determination to break free.

### Survival and Adaptability

Jack Black adapts to jail life, engages in various schemes, and eventually escapes to survive.

## Character check-ins

### Irish Annie

Jack Black initially hates her for betraying him, but later receives money orders from her after her death, which softens his hatred.

### Dirty Dick

Captain at Folsom prison, known for his brutality and bullying of new prisoners.

### Sam Newburgh

Jack Black's new lawyer, chosen for his tenacity and willingness to support clients financially.

### Fremont Older

Editor of The Call who visits Jack Black in jail and attempts to help him get probation.

### Judge Frank H. Dunne

The judge who sentenced Jack Black and refused Fremont Older's suggestion of probation.

### Blacky

Jack Black refers to himself by this alias; his rescuer calls him 'Blacky' when saying goodbye.

## Key lines

> My first few months in the county jail were put in hard enough. About all I did was hate Irish Annie, and plan ways and means to revenge myself on her.

Jack Black spent his early jail time consumed by hatred for Irish Annie and plotting revenge.

_Highlights his initial emotional state and focus on betrayal._

> I went to prison without any plans for the future. With good conduct I would have to do five years and four months and there was no use trying to look that far ahead.

Jack Black entered prison with no plans, facing a long sentence that made future planning futile.

_Shows his resignation and the weight of his sentence._

> For once all my mistrust, suspicion, and hatred vanished. I said: 'Mr. Older, I’m afraid you will waste a lot of valuable time trying to do anything for me.'

Jack Black's usual distrust disappeared when meeting Fremont Older, and he honestly expressed his hopelessness.

_Demonstrates a rare moment of vulnerability and trust._

> Opium, the Judas of drugs, that kisses and betrays, had a good grip on me, and I prepared to break it.

Jack Black personifies opium as a betrayer and resolves to overcome his addiction.

_Illustrates his struggle with addiction and determination to quit._

## Links

- HTML: https://www.betterreads.online/discover/you_can_t_win_se/chapters/xxiii
- Book: https://www.betterreads.online/discover/you_can_t_win_se
- All chapters: https://www.betterreads.online/discover/you_can_t_win_se/chapters