Duddy pelts Mr. MacPherson with snowballs and draws an insulting picture of him on the chalkboard on his first day.

Duddy realizes his father Max is a pimp and Max strikes him hard across the face when Duddy says so.

Simcha tells young Duddy that a man without land of his own is nothing.

Duddy takes a job as a hotel waiter and is repeatedly humiliated by a wealthier college-boy waiter named Irwin.

Duddy loses every dollar of his summer savings at Irwin's rigged roulette game and sobs alone outside the hotel.

Duddy visits a secluded lake with Yvette and declares he will buy the surrounding land to build a camp.

Duddy persuades the alcoholic filmmaker Peter Friar to go into business making films of bar mitzvahs and weddings.

The Cohen family loves Friar's bizarre, artistic bar mitzvah film, giving Duddy's new film company its first success.

Lennie abruptly disappears from home, leaving behind only a note saying he will not return to medical school.

Duddy travels to Toronto, finds Lennie, and learns that Irwin's group manipulated Lennie into performing an illegal abortion.

Virgil has a massive seizure while driving a delivery truck alone and is left permanently wheelchair-bound.

Yvette resigns from Duddy's company and moves to the countryside to become Virgil's full-time caregiver.

Duddy steals money from Virgil by forging two of his checks while Virgil is upstairs.

Simcha refuses to leave the car or set foot on Duddy's land after Yvette tells him how Duddy obtained the money.

Yvette tells Duddy that Virgil never wants to see him again and that she and Virgil are gone from his life.

Duddy Kravitz grows up in Montreal harassing teachers and discovering his father is a pimp, guided only by his grandfather Simcha's belief that a man must own land. After losing all his summer savings at a rigged roulette game at a resort hotel, Duddy finds the lakeside property he becomes obsessed with purchasing. He builds a film company from scratch, scoring an unlikely hit with a bizarre bar mitzvah film, while racing to acquire each parcel of the lakefront land. When Duddy's devoted helper Virgil is left wheelchair-bound after a dangerous job Duddy assigned him, Yvette walks away and Duddy's life spirals. Desperate and nearly broke, Duddy forges Virgil's checks to buy the last of the land and achieves his lifelong dream. But the triumph is hollow: Simcha refuses to step onto the stolen property, and Yvette delivers the final blow by declaring that Virgil never wants to see Duddy again.

Duddy's rise from troublemaker to land owner and ultimate downfall.

MacPherson, drunk and devastated by his wife's death, finally breaks his principles and beats Duddy with a leather strap.

MacPherson collapses in the classroom and the school principal sends him on a leave of absence to recover.

Duddy is caught in a compromising state at Benjy's dress factory and his uncle warns him he is being watched.

Duddy befriends the local Jewish comic Cuckoo at the hotel and the two devise various get-rich-quick schemes together.

Linda takes Duddy on a date but disappears with another man, returning an hour later with leaves in her hair.

Duddy returns home after quitting his hotel job, is barely acknowledged by Max, and quietly gives Lennie thirty dollars.

Duddy meets filmmaker Peter Friar at a cinema club and is left with a large drinks bill when Friar slips away.

Jerry Dingleman gives Duddy a suitcase and pays him $550 to carry it through customs without asking any questions.

After the bar mitzvah success, Peter Friar makes a romantic pass at Yvette and tells her Duddy will never marry her.

Duddy visits Hugh Calder to protect Lennie's secret and leaves the meeting with Calder's admiration and contact information.

Duddy sells illegal pinball machines at countryside hotels with the unexpected help of Virgil, a stranger he just met.

Duddy's alliance with Hugh Calder falls apart permanently after he tries to renegotiate their scrap towing arrangement.

Duddy strikes Yvette during an argument about his callous treatment of Virgil following the truck accident.

Duddy's film business collapses and he declares bankruptcy, reduced to driving his father's taxi to earn money.

Duddy tries to blackmail Jerry Dingleman over the drug smuggling, but Dingleman counters by threatening to expose Duddy's pinball machines.

This pool follows the secondary relationships and schemes that shape Duddy's journey, from his earliest clashes at school to his criminal dealings with the Boy Wonder. MacPherson's broken principles and Uncle Benjy's factory warning establish early patterns of Duddy's manipulative behavior, while Cuckoo and Linda reveal his ambitions and insecurities at the resort hotel. Back in Montreal, Duddy exploits filmmaker Friar and is exploited in turn by drug smuggler Dingleman, while his audacity wins a reluctant ally in Hugh Calder — a bridge Duddy later burns by overreaching. He puts Virgil in dangerous work, strikes Yvette during an argument, and watches his business collapse into bankruptcy as each relationship he has damaged falls away. The pool closes with Duddy's failed blackmail attempt against Dingleman, showing how every bridge he burns leaves him with fewer options and fewer people willing to help.

The people Duddy uses, betrays, and burns along the way.

MacPherson's wife Jennie collapses and is found on the floor after Duddy's prank call draws her out of bed.

Duddy quits his hotel job, tells Linda to go to hell, and runs off to find Yvette after the roulette disaster.

Duddy tells Simcha about his plan to buy the lake, and Simcha says he is becoming a good man and is proud.

Duddy's offer on the lakefront property is accepted before he has secured anywhere near the required funds.

Mr. Cohen takes pity on a desperate Duddy and agrees to hire his film company for his son's upcoming bar mitzvah.

Duddy waits hours to see the Boy Wonder Jerry Dingleman only to discover Max invented their close personal friendship.

Duddy refuses to leave Sandra Calder's home until she breaks down and writes Lennie's hiding address on a piece of paper.

Duddy hires Virgil at embarrassingly low wages; Yvette vanishes in protest and returns only when Duddy raises the pay.

Duddy runs into a startlingly thin Uncle Benjy on the street, and Simcha later confirms the illness is cancer.

Duddy retrieves Aunt Ida from New York, and on the train home she reveals that she was the one unable to conceive.

Benjy offers Duddy his entire business in his will; Duddy refuses, then breaks down pleading with the doctor to save Benjy.

Duddy tearfully confesses to Hersh that his prank call contributed to MacPherson's wife leaving her sickbed and dying.

Duddy reads Uncle Benjy's posthumous letter, in which Benjy apologizes for underestimating him and urges him to live honestly.

The Boy Wonder is arrested for drug smuggling, and Duddy calls Lennie to ask about heroin as he begins a new scheme.

Duddy chases after Simcha at the lakeside property and desperately pleads for his grandfather's approval and pride.

This pool tracks the moments of revelation and moral consequence that define Duddy's character across the full arc of the novel. From the guilt-laden truth that his prank call contributed to MacPherson's wife's death, to his grandfather's quiet praise that deepens his obsession with owning land, these events show how Duddy's choices ripple outward in ways he rarely anticipates. Key turning points include the desperate scramble after his property offer is accepted without funds in hand, his discovery of Max's fabricated friendship with Dingleman, and his coercion of Sandra Calder into revealing Lennie's hiding place. The middle section lays bare painful family truths — Benjy's cancer, Ida's confession about her infertility, and Duddy's defiant refusal of Benjy's business legacy. The pool closes with Duddy reading Benjy's posthumous plea for decency and then chasing his silent grandfather across the very lakeside land he had to steal to own.