Dexter is Our Hero, the main character of "Winter Dreams." But what kind of hero is he exactly? Certainly not your typical one. Dexter's main goal in life is to make tons of money and improve his social class. He dreams of actually playing golf with the rich men he caddies for at the Sherry Island Golf Club. Still, while Dexter may dream of fame and fortune, this is not a rags-to-riches tale. He's actually a middle-class kid, the son of the second-most successful grocer in all of Black Bear, Minnesota. So what is Dexter's beef with his quality of life? What makes him so ambitious?
Dexter can't settle for comfortable. He wants all of the grace and beauty that seems to go along with extreme wealth. And when Dexter becomes infatuated with the beautiful Judy Jones when he is just fourteen, winning her becomes equal to winning wealth, at least in Dexter's young mind.
Because Judy's beauty draws Dexter to her, we know that, on top of money, appearances are super-important to our young hero. Plus, he opts to go to an expensive, high-class East Coast college instead of a local state school to study business, mainly because of the East Coast school's prestige. But still, he's not just a snob. He just wants absolutely the best for himself: "He wanted not association with glittering things and glittering people — he wanted the glittering things themselves" (2.1).
Dexter ends up doing pretty well for himself. He makes tons of dough by investing in a chain of high-end laundries in a nearby Minnesota city. He sells the laundry chain at a profit and takes his money to New York, where he becomes a great investor. By the end of "Winter Dreams," Dexter is living the high life as a Wall Street businessman. Sounds like a happy ending, right?
But somewhere along the way, Dexter has changed. We see this change about midway through "Winter Dreams," when Dexter ditches his fiancée Irene for Judy Jones. Dexter has always been an idealistic dreamer. He had plans.
When he leaves Irene behind, he feels some guilt, of course, but mostly he thinks that there "was nothing sufficiently pictorial about Irene's grief to stamp itself on his mind" (5.1). In other words, even though Dexter likes Irene and her family, her sadness isn't a pretty enough image to make him feel truly guilty about leaving her behind.
We already know that Dexter really, really cares about how things look, and not so much about how they are. But his response to Irene shows a new level of superficiality. Is he turning hard and cold inside? Where's the bold and optimistic dreamer we knew before?
Following this broken engagement with Irene and the inevitable train wreck that is his relationship with Judy, Dexter joins the army to fight in World War I. And after the war, he moves to the East Coast and joins the Wall Street business world. As Dexter moves further and further away from his boyhood home of Black Bear, Minnesota, he is also leaving behind the dreamy boy that he once was.
But isn't that just a consequence of growing up? Maybe Dexter's just finally getting a dose of reality. Yet we know that since the title of this whole story is "Winter Dreams," those dreams are important. Abandoning them might mean more in this story than simply becoming mature.
The real change in Dexter's character is only confirmed by the end of the story. When Dexter hears that Judy Jones has lost her beauty and married some guy who steps out on her and drinks too much, he freaks out. But Dexter doesn't start crying because of Judy. What's bothering him is that he cannot feel bad enough about Judy. He isn't even that sorry to hear that she is having a tough life: "He wanted to care, and he could not care" (6.35). Something has happened inside of him, something bad, something to do with those dreams.
Think about it: Judy Jones is the woman who Dexter has loved for over fifteen years, through good times and bad. Even when he starts to realize that the high life is not all that it is cracked up to be, Dexter still maintains this idealistic attachment to Judy Jones, despite her less-than-appealing personality traits. But now that ideal is gone, and Dexter suddenly realizes that he has changed. His own dreams, which were wrapped up in Judy's beauty, have faded away without him even noticing. All he's got left are piles of money that he has earned. The narrator sums up:
The gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time. Even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished. (6.35)
Dexter has "gone away," but from where? And to where? Let's think about this. First, he has literally left behind his home in Black Bear, Minnesota, where he first began to dream big about the good life. He has also left the Sherry Island Country Club, where he spent his first happy, romantic months with Judy feeling hopeful about the world and his place in it.
Plus, he has left behind those more general fantasies of the glamor and charm of the high life. Those winter dreams are somewhere in his past. Now he knows that money means hard business sense: there is nothing romantic about it at all.
All that Dexter has left is his financial success. He looks like he has been "born and raised on Wall Street" (6.3), which is what we thought he wanted in the first place. But to reach this level of wealth and power, Dexter has had to give up all of his early illusions of love and beauty. He has had to forget where he comes from. So when he mourns at the end of "Winter Dreams," it's not Judy Jones he remembers; Dexter cries for his own boyhood.
We mentioned in "In a Nutshell" that author F. Scott Fitzgerald gets the setting for "Winter Dreams" from his own experiences growing up in Minnesota. But Dexter and Fitzgerald share more than their Minnesotan histories. Fitzgerald himself experienced a similar transformation that Dexter undergoes by the end of "Winter Dreams."
Take a look at this excerpt from Fitzgerald's 1937 essay, "Early Success." We don't know about you, but Shmoop thinks it sounds eerily similar to Dexter. As Fitzgerald remembers looking down on the glitz and glam of the French Riviera in the 1920s, he thinks about himself as a poorer, younger man:
[I was looking] back into the mind of the young man with cardboard soles who had walked the streets of New York. I was him again – for an instant I had the good fortune to share his dreams, I who had no more dreams of my own. And there are still times when I creep up on him, surprise him on an autumn morning in New York […] But never again as during that all too short period when he and I were one person, when the fulfilled future and the wistful past were mingled in a single gorgeous moment – when life was literally a dream. (Source.)
Of course, there are other, more mundane similarities between the author and his character. Both Dexter and Fitzgerald start out in the Midwest and come to the East Coast in search of fame and fortune. Both serve in the army during World War I. Dexter is a businessman and Fitzgerald, a writer, but both have dreams of a romantic future that success will bring them – and that's the part we're interested in.
While Dexter is actually financially successful, Fitzgerald goes on to spend much of his life dealing with declining sales and alcoholism. But both Dexter and Fitzgerald have to face the disillusionment of success (meaning, success isn't usually as wonderful as it seems). In the final paragraphs of "Winter Dreams," Dexter faces the truth that the reaching his goals has actually led to the loss of the romantic ideals that gave rise to those dreams of wealth and beauty in the first place. Fitzgerald, too, remembers his own dreams of a brilliant future, from the perspective of a man who has "no more dreams of [his] own."
But here's the crazy part: Fitzgerald wrote "Winter Dreams" in 1922, before he could know his own later disappointments with money, love, and writing. So it's almost as if "Winter Dreams" predicts Fitzgerald's own later nostalgia for a time when he, like Dexter, had dreams. Writer and fortune-teller? Seems like it to us.