If memory serves, he was actually a Midwesterner. However, he did die in the west -- eating a candy bar in the sunshine.
Never saw him as anti-establishment. Always saw him as the quintessential American -- conflicted, awed, anxious and, above all, moral.
Now take O'Hara, there was a guy ready to mix it up.
"One of my most vivid memories is of coming back West from prep school and later from college at Christmas time. Those who went farther than Chicago would gather in the old dim Union Station at six o'clock of a December evening, with a few Chicago friends, already caught up into their own holiday gayeties, to bid them a hasty good-by...And last the murky yellow cars of the Chicago, Milwaukee and St. Paul railroad looking cheerful as Christmas itself on the tracks beside the gate.
When we pulled out into the winter night and the real snow, our snow, began to stretch out beside us and twinkle against the windows, and the dim lights of small Wisconsin stations moved by, a sharp wild brace came suddenly into the air. We drew in deep breaths of it as we walked back from dinner through the cold vestibules, unutterably aware of our identity with this country for one strange hour, before we melted indistinguishably into it again.
That's my Middle West — not the wheat or the prairies or the lost Swede towns, but the thrilling returning trains of my youth, and the street lamps and sleigh bells in the frosty dark and the shadows of holly wreaths thrown by lighted windows on the snow. I am part of that, a little solemn with the feel of those long winters, a little complacent from growing up in the Carraway house in a city where dwellings are still called through decades by a family's name. I see now that this has been a story of the West, after all — Tom and Gatsby, Daisy and Jordan and I, were all Westerners, and perhaps we possessed some deficiency in common which made us subtly unadaptable to Eastern life.
Even when the East excited me most, even when I was most keenly aware of its superiority to the bored, sprawling, swollen towns beyond the Ohio, with their interminable inquisitions which spared only the children and the very old — even then it had always for me a quality of distortion. West Egg, especially, still figures in my more fantastic dreams. I see it as a night scene by El Greco: a hundred houses, at once conventional and grotesque, crouching under a sullen, overhanging sky and a lustreless moon. In the foreground four solemn men in dress suits are walking along the sidewalk with a stretcher on which lies a drunken woman in a white evening dress. Her hand, which dangles over the side, sparkles cold with jewels. Gravely the men turn in at a house — the wrong house. But no one knows the woman's name, and no one cares.
After Gatsby's death the East was haunted for me like that, distorted beyond my eyes' power of correction. So when the blue smoke of brittle leaves was in the air and the wind blew the wet laundry stiff on the line I decided to come back home." -- Chapter Nine