How we cite our quotes:
In the fall when the days became crisp and gray, and the long Minnesota winter shut down like the white lid of a box, Dexter's skis moved over the snow that hid the fairways of the golf course. At these times the country gave him a feeling of profound melancholy – It offended him that the links should lie in enforced fallowness, haunted by ragged sparrows for the long season. It was dreary, too, that on the tees where the gay colors fluttered in summer there were now only the desolate sand-boxes knee-deep in crusted ice. When he crossed the hills the wind blew cold as misery, and if the sun was out he tramped with his eyes squinted up against the hard dimensionless glare. (1.2)
The words that Fitzgerald uses to describe winter in Black Bear, Minnesota are pretty bleak: "profound melancholy," "cold as misery," "hard dimensionless glare." Yikes, not a place where we'd want to hang out, that's for sure. This winter contrasts strongly with the space of the golf course, where "the gay colors fluttered in summer." The Sherry Island golf course is where young Dexter first sees what it would be like to be loaded. When it shuts down for the winter, Dexter is left on his own to dream about what that wealthy life would be like. In a way, it's in winter, at the time of the year when the golf course closes, that Dexter is closest to that space of luxury. It's when he is not caddying that he can dream of becoming a wealthy man himself. And boy does absence make the heart grow fonder.
[His winter dreams] persuaded Dexter years later to pass up a business course at the State university – his father, prospering now, would have paid his way – for the precarious advantage of attending an older and more famous university in the East, where he was bothered by his scanty funds. But do not get the impression, because his winter dreams happened to be concerned at first with musings on the rich, that there was anything merely snobbish in the boy. He wanted not association with glittering things and glittering people – he wanted the glittering things themselves. (2.1)
This choice Dexter makes to go to a famous East Coast school instead of a Minnesota state school tells us something about the particular nature of his ambition. He doesn't just want to make a ton of money. He also wants the kind of social standing that an Ivy League degree can give. In other words, it's not just about cash – it's about class. Wait, this isn't snobby? We beg to differ.
[Dexter] knew that to be careless in dress and manner required more confidence than to be careful. But carelessness was for his children. His mother's name had been Krimslich. She was a Bohemian of the peasant class and she had talked broken English to the end of her days. Her son must keep to the set patterns. (3.2)
Dexter is completely aware of what it's going to take for him to join the wealthy upper classes in America. He is the son of an immigrant, so he can't be careless about his manners. Instead, he has to stick as closely as he can to the social codes of the rich. Once Dexter has proven himself, his children can afford to be looser, less conventional, and more Judy-Jones-like.