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America in the early part of the 20th century was a place rife with wealth, and the wealth was growing. While Lefty and Desdemona aren't living a life on par with Leonardo DiCaprio's Gatsby in Middlesex, they have a lot of earning potential. And the way to make to money is through work. The work of Cal's ancestors affects who they are, whether they're working in factories, smuggling liquor into Canada, or peddling hot dogs. Since Cal is a product of his ancestors, we're surprised he isn't working in some sort of hot dog-flavored liquor factory.
The men of the Stephanides family are focused on one thing: earning money to support their family. Earning money comes at the price of being close to family.
Each generation of Cal's family is wealthier than the previous one⦠until Chapter Eleven bankrupts the family business, that is. We have no idea how they fare after that happens.