The Apprenticeship of Duddy Kravitz, by Mordecai Richler, originally published in 1959, follows the exploits of a working-class Jewish boy growing up in a turbulent neighborhood and family in Montreal, Canada. Told in four parts, the novel chronicles Duddy’s relentless pursuit of higher social status and monetary success. Duddy travels on both sides of the law in his business dealings, keeping company with moguls and outlaws alike. He ends up working in industries that he knows little to nothing about—high-end soaps, artistic films—and still turning a profit. He both charms and repulses those who get to know him, but his force of personality cannot be denied.

The focal point of Duddy’s ambition is the acquisition of land. From his Polish immigrant grandfather, Simcha, Duddy’s been taught that a man is nothing if he doesn’t own land. As he grows up in the city, this plan seems far-fetched. It isn’t until he takes a demeaning job waiting tables in an upscale countryside hotel that Duddy finds the land that he’s determined to make his own. Like an old-world explorer, Duddy creates a map of his dream property, which he envisions as a campsite for Jewish kids, and gradually works on acquiring each individual parcel of land.

Duddy’s family supports and derides him. He is undervalued by his father, Max, a taxi driver who earns extra money as a pimp. Max believes that Duddy is a dunce like him and that all the family’s hopes lie with Duddy’s older brother, Lennie. Lennie cares for Duddy and would like to be more of a role model, but Lennie is too busy desperately trying to please his father and society in general. Simcha, the family patriarch, believes in Duddy but in a quiet way, too quietly to outweigh the loud negativity espoused by Duddy’s uncle Benjy, a successful business owner who thinks Duddy is just greedy and crass.

Duddy manages to establish a little support team to assist him in his professional goals. Some of the individuals Duddy relies on the most are unable to find a path for themselves beyond dependence on Duddy. Mr. Friar, a wasted-up drunk of a filmmaker, needs Duddy’s direction and connections to keep working. Virgil, an epileptic, cannot secure another job because of his condition and offers to do any job Duddy asks of him. Other members of Duddy’s support team are more affluent and established. Mr. Calder, the father of a woman Lennie performs an illegal botched abortion on, becomes an unlikely supporter of Duddy’s. Mr. Cohen, a successful business owner, is another supporter, giving Duddy seed money in the interest of helping out a fellow Jew.

But ultimately Duddy ends up devaluing and losing those who love him most. He consistently takes his girlfriend, Yvette, for granted, despite the fact that she is the one who helps him hone his dream and forge the plan to make it a reality. He manipulates Virgil, his devoted friend, giving him a job that is too dangerous given Virgil’s condition. Duddy wrongs Virgil a second time, stealing from him, even after Duddy’s carelessness has rendered Virgil wheelchair bound. The most stinging loss for Duddy, though, is the loss of his grandfather’s respect. When Simcha finds out that Duddy has achieved his dream of land ownership only via theft and manipulation, he refuses to offer Duddy the congratulations and praise that Duddy so desperately craves. Without the patriarch’s validation of his success, all Duddy can do is start over, try to carve out another dream, and make new choices. The novel ends with Duddy getting on a bus, attempting to start over.