What happens as he grows up and his siblings and him become increasingly caught up in the crime wave sweeping that part of the city... is bad. Very very bad. You have been warned.
MacDonald planned to write a movie script based off the book for director Ron Shelton, but this project fell into limbo.
This book provides examples of:
- All Girls Want Bad Boys: Essentially why Kevin's wife Laura fell in love with him.
- Angrish: Helen falls into this after having a minor stroke.
- Anyone Can Die: To the point where Long List is invoked just to show how many family friends end up dead. Also three of Michael's brothers die over the course of the book.
- Bad Cop/Incompetent Cop: The police system is mostly on the payroll of Bulger or one of his associates.
- The Chessmaster: "Whitey" Bulger. No matter how much of his organization gets taken down by the police or the FBI, he manages to keep himself clean. At the end, he gets his comeuppance and goes on the run.
- Cool Old Guy: Michael's grandfather (Helen's father) falls into this, frequently trying to help out (sometimes in odd ways) and not afraid of facing down local gangsters.
- Despair Event Horizon: Kathy, after she inadvertently burns down her apartment.
- Driven to Suicide: Davey, due to mental issues.
- Drowning My Sorrows: A variant occurs at the funeral of Frankie: Helen tries cocaine just to dull the pain. Michael himself responds in the more conventional method of drinking whiskey.
- Everyone Has Standards: Whitey Bulger is well known for not drinking, smoking and taking care of his body, as well as being active in his community, but he also becomes a notoriously violent gangster who was secretly in charge of drug distribution in Southie while pretending to be against drugs, making him some combination of Straight Edge Evil and Hypocrite.
- From Bad to Worse: Just when Michael thinks his mother can't handle another tragedy...well, cue another tragedy.
- Go Among Mad People: This is what happens to Davey. While he did have mental issues, his time in the mental hospital only made it worse.
- Harmful to Minors: Michael (and his siblings) end up witnessing a large number of beatings, assaults, and other general violent acts.
- He Knows Too Much: This is why Kevin is murdered by the mob.
- Heroic BSoD: Helen has one after Frankie's death, and then Michael himself has one after his brother Steven is found guilty of a crime he didn't commit.
- Hope Spot: Frankie looks like he might become the next big professional boxer right before his death as part of a heist on an armored car.
- The Irish Mob: This is the real deal.
- Lovable Rogue: MacDonald explains that this was Whitey Bulger's general reputation in South Boston until the true extent of his bloodthirstiness, corruption and hypocrisy came to light after he fled town. Basically everyone knew he was up to no good, but exactly how much was a shock.
- Madness Mantra: "Ding dong, the wicked stick is dead..."
- Mama Bear: Helen, who went and tried to take down the crime rings after her sons' deaths, and later filed a lawsuit on behalf of Kathy against the state of Colarado. See Pregnant Badass also.
- Obstructive Bureaucrat: Lots of them, many working with Bulger's organization.
- Opt Out: Helen eventually gets fed up with dealing with life in South Boston, and moves to Colorado.
- Police Brutality: In full effect. The police are willing to beat anyone, even children, in order to stop riots.
- Pregnant Badass: Helen being an actual real life example, beating up someone while eight months pregnant.
- Sanity Slippage: Davey and later Kathy both end up gradually losing their grip.
- Southies: Most of the people in the book, which is to be expected.
- Villain with Good Publicity: Whitey Bulger again, and while no one had any doubts he was a gangster this image was only shattered at the revelation that he was also working as an informant for the FBI.
- Wretched Hive: South Boston, as described here, fits this trope perfectly.
