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Hole in My Life – Chapter Summaries
Part One
Chapter 1 – “look straight ahead”
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Jack relates his experience in prison – constantly in fear
Works as an x-ray technician – provides him with private cell and ability to stay out of general
population – safer
Father always able to spot criminals (except for Jack)
Being locked up in prison provided opportunity to change his life for the better  wrote
Chapter 2 – “misfit”
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At 19, Jack lived on his own in St. Croix – parents moved there for father’s construction job –
Jack worked wiring rooms – eventually decided to return to FL and go to school
Lived with Bacons – partying crazily  Bacons kicked him out
Lived at The King’s Court, run by Davy Crockett, the 4th, a tough old lady
Chapter 3 – “king’s court”
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Jack lives on his own and attends high school, as a senior
Relates how he keeps a diary – had since elementary school
School was a former prison – ex-cons came once and spoke about dangers of crime
Smokes marijuana for first time with friend Glen
Applies to and is accepted to the University of Florida  turns it down
Chapter 4 – “pair of jacks”
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Jacks relates reading On the Road by Jack Keruoac – see himself as a combination of two
protagonists, Sal and Dean – wants to travel the country, write and “somewhere along the line
the pearl would be handed to me.”
Runs into old friend – Tim Scanlon – gives Tim half his money to buy marijuana to make more
money  Tim steals money and later tells Jack that college security took the marijuana
Part Two
Chapter 1 – “st. croix”
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Returns to St. Croix, where marijuana is readily available – smoking continuously
Racial tension is high: Jack and father build crates for people to ship belongings back to the U.S.
Meets Rik, who asks for crate with false bottom for shipping drugs
Goes to Black Revolutionary Party Headquarters, looking for a good story, and is treated poorly
Rik offers him job – will pay $10,000 to help sail boat with hash to Florida – meets Hamilton
Chapter 2 – “bon voyage”
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Hamilton and Jack are terrible sailors – disastrous practice runs
They dig up the has on Little Dog Island and set sail for NYC
Jack eats hash every day, and Hamilton drinks hash in his tea
Hamilton behaves strangely – stops wearing clothes, paces, has mood shifts
Jack calls the ship “a strange floating cell.”
Chapter 3 – “ship’s log”
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Hamilton throws away Jack’s identification except for his fake Florida license
Jack keeps a journal (ship’s log) of what happens on the trip to NYC
Have interaction with Japanese fishing boat
Coast Guard plane flies overhead – Jack waves
Arrive in Cape May, NJ
Chapter 4 – “I love new york”
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Jack relates “getting-caught stories”
Hamilton and Jack arrive in NYC - contact Rik
They deliver all the marijuana, and Jack is paid his money
FBI shows up and go after Hamilton  Jack escapes and flies to Ft. Lauderdale
Part 3
Chapter 1
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Jack talks with his father – learns that the FBI is after him – hires Al E. Newman to represent Jack
Jack returns to NYC  goes back to Chelsea Hotel – all their stuff is there except for ship’s log
Meets with Newman  go to Tepper’s (prosecuting attorney) office: Tepper says “airtight case”
Jack learns that the FBI caught Rik before Hamilton and Jack left St. Croix – FBI followed their
progress to NYC the entire trip, taking photos from the Coast Guard plane
Newman assures Jack that he won’t go to jail because he is just a kid – Jack accepts a plea for
one count of conspiracy to distribute
Chapter 2 - “face-to-face”
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Jack stays at Chelsea Hotel, waiting for sentencing – his face breaks out in terrible acne
FBI agents follow him everywhere
Jack takes his two pounds of hash and buries it in Central Park
Chapter 3 – “a long, long day”
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Court
o Tepper presents the evidence (photos) and says that Jack is withholding information
o Newman argues that Jack is young and made a big mistake, but he has a positive future
o Judge accuses Jack of making the mistake of getting caught
o Tepper reads the ship’s log – Jack wrote “I’m just afraid of the punishment.”
o Judge sentences Jack to 6 months to 6 years, depending on behavior and parole board
Jack’s dad brings car insurance papers – Jack’s dad drove car over cliff for insurance money
Bus to jail – everyone sniffing: fear, sour sweat, smell of exhalation, lunch, bile, illness
At jail – an inmate offers to be Jack’s master in return for keeping him safe
Jack finds Lucas in bathroom stall – Lucas has been repeatedly raped – Jack eager to get away
from Lucas – doesn’t want to be a victim too
Chapter 4 – “my yellow cell”
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Jack arrives at prison with lice so is put in private cell – counted in 6x/day
Starts a journal – writing between the lines in a Dostoyevsky novel
Three Muslim Brotherhood men come by cell, asking him to “trust” them – looking for sex
Lice are gone – Jack will have to enter general population but asks the physician’s assistant if the
hospital needs help  becomes x-ray technician – stays out of general population
Chapter 5 – “drug lust”
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Drugs are everywhere in prison – inmates use drugs to lessen the stress and pain of being in jail
Jack stays away from drugs – doesn’t want to get caught – wants to get out of prison
After 5 months, meets with parole board who ask about where the hash and money is  deny
him parole
Jack starts writing about his childhood, which gives him pleasure
Chapter 6 – “marking time”
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Jack reads his file
o the parole board called him “uncooperative and unwilling to tell the truth”
o the psychiatrist called him a “situational sociopath” unwilling to “honestly describe
himself” – basically a liar
Jack’s dad and uncle visit – they are drunk and come on a non-visiting day
Jack goes to see the shrink again, who tells Jack that he should tell the truth and to come back
when he is ready
Jack continues writing – realizes that life outside prison is more interesting than prison life
Chapter 7 – “getting out”
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Jack relates stories about attempted escapes
Jack gets a new caseworker – Mr. Casey (young, helpful) – Jack decides to apply to college
Applies to Graham Junior College – Mr. Casey mails application from home (no prison stamp)
Jack is accepted  parole board grants parole – Jack is out if he has a stable place to live and a
job
Chapter 8 – “a closed book”
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Jack leaves – not allowed to take his journal – is sad because his “heart was in that book”
Jack goes to NYC to live with friend of his dad and works selling Xmas trees
Jack starts school – becomes security guard as part of work-study program at school
Writing classes: first writes about prison but then starts writing about childhood
Then starts writing books for children – Rotten Ralph series
Never returned to dig up the hash, although he got close
Got the ship’s log back years later but never could get the prison journal
Now “I’m out in the open doing what I have always wanted to do. Write.”