"Winter Dreams" can be seen as a Modernist text in a couple of ways. If we accept the premise of Modernism that the movement seeks to display a condition in which there is a "shift" between the relationships that people have towards one another, themselves, and their world, then the narrative shows this in a couple of ways. Initially, I think that Fitzgerald displays Modernism in the entire premise of self- improvement. The traditional notion is that an individual works hard, becomes successful, and in doing so represents a harmonious connection between themselves and the world around them. Fitzgerald inverts this Horatio Alger "rags to riches" story in displaying that the more Dexter becomes successful, the more alienated and divided he becomes. Dexter's unhappiness gains as he becomes more successful because his "Winter Dreams" are fundamentally corroded. The vision that Fitzgerald offers of material success is a Modernist one, in which happiness is elusive no matter what.
The text is also Modernist in its ending. In this, a "shift" is seen because of its dissonance. Simply put, there is no resolution in this condition. Dexter was unhappy when he didn't have Judy Jones. Judy Jones was shown to be this ideal that motivated Dexter. He was then unhappy when he had Judy Jones because of her infidelities and her unwillingness to emotionally commit to him. Dexter is then finally shown to be unhappy when his life moves past Judy Jones and then hears about her loveless marriage and her faded beauty. It is here in which Dexter cries about "That thing is gone." This is a Modernist progression because it does not show anything in way of freedom or happiness. There is only alienation and desolation waiting for the modern individual, a shift from the traditional construction of happiness and contentment that was previously understood.