Not long ago I received an aerial photograph of several enormous white houses stuck together. This is one house, actually, my grandmother’s, in Westchester County, New York State. During my childhood, driving over to see my grandparents was known as ‘visiting the Big House’. The federal penitentiary, Sing Sing, just up the Hudson River from Westchester, is also known as the ‘Big House’. When you are tried and sentenced to jail, it’s still known, all over the United States, as getting ‘sent up the river’, in honour of Sing Sing, even though Westchester’s white-collar criminals know they will never end up anywhere close.

Hillary Clinton’s independent political career began when she and Bill moved to Westchester, to Chappaqua, fifteen minutes away from my grandparents and their Big House, and took out a mortgage on a place of their own large enough to blend inconspicuously in with the neighbourhood. The shame I feel at looking at photographs of the Big House doesn’t go away, even when I realize that, with the arrival of the Clintons in my old neighbourhood, nobody calls my grandparents phoneys any more.

‘Why are you moving to Westchester, Mrs Clinton?’ the New York Times and New York Newsday and the New York Daily News all asked.

Hillary confided that she admired the county’s beauty and its ‘stately homes’. In the richest parts of Westchester, a house is not a house, it is a Home. In many parts of the county, including Chappaqua, the Homes are invisible from the road, set off at the ends of private driveways, sometimes patrolled by private police.

When Hillary and Bill moved into their new Home, it was big news in Westchester. Kids rode around Chappaqua on their mountain bikes, reporting Clinton-sightings into cellphones, like miniature versions of CNN’s Peter Arnett in the Persian Gulf. The local evening news showed Hillary’s removal van. We heard her unpack on National Public Radio. There was a voice-over, as in sportscasting. ‘I think a lot of her unpopularity has to do with carpetbagging,’ the commentator said. ‘It’s a high-intensity issue for those that don’t like her.’

‘Carpetbagger’, an epithet from the end of the Civil War, was originally a term for white Northerners who went down to the ruined cities of the post-bellum South to make their fortune. The Clintons had given this elderly insult a new life. The word has overtones: of social climbing, of using people and places transparently, of hick vulgarity, of crashing the party.

The Clintons’ house quickly became Westchester’s answer to Graceland, the object of Sunday morning drives and the target of radio talk shows. People took the train in from the city to see the Clintons’ new Home. David Letterman posed in front of it. There hadn’t been this much attention paid to Westchester since Herman Tarnower, the Scarsdale Diet Doctor, was murdered in the late Seventies, shot in the head by his mistress, an elementary school principal. The next day Tarnower’s house, mailbox and driveway could be seen on Eyewitness News: they resurfaced shortly afterwards in People magazine. Every one of us who had ever choked down two weeks of Scarsdale Diet grapefruits—in other words, every woman in Westchester over eleven—felt, suddenly, brightly, in the public eye. Even those of us who couldn’t forgive Tarnower his hardboiled-egg dinners and spinach lunches forgave him everything. From then on, something was established, something we remembered twenty years later when Hillary moved in. Westchester seemed to finish off its celebrity residents, one way or another.

My grandparents bought the Big House when my father was thirteen, in 1947, before most of Westchester’s present residents were born. Hillary’s critics like to point to people like my grandparents, born in Manhattan or the Bronx, with accents thick enough to subtitle. Unlike Hillary, they are real New Yorkers. It doesn’t make them any less real or less New York to add that they were fakes from the beginning.

When I ask my grandmother what she thinks of Hillary, she is unequivocal: Hillary is not a New Yorker. She is not from New York. She does not understand New York. She is not real. My grandmother adds that she herself is still a supporter of the Democratic Party. Now that Hillary is in the neighbourhood, she quips, she is looking forward to the Democratic…parties. Since my grandmother was born on the Lower East Side, it comes out ‘pah-tees’. She then tosses back her head in a laugh that shows me her teeth.

My grandmother is eighty-nine. Her teeth are still hers, her eyebrows are not. Every morning, in a cracked marble bathroom, she plucks them out and paints them back in, along with a beauty mark, like the music-hall flappers of her adolescence. Her hair is a sculptured helmet; it has not been allowed to go white and is instead a delicate, greenish grey-yellow. She puts on a girdle, a garter belt, old-fashioned hose which snaps on to garters, and stuffs her feet into two-tone pumps which still arch her ankles and point her toes with a dusty Forties flirtatiousness. Women of my grandmother’s generation do not wear pants, and after seventy-five years of garter belts and hose her legs are as white and smooth as the marble tile underfoot. Both my grandparents have a thing for marble. I’ve used my grandmother’s personal bathroom twice in my life (the house has seven) and both times something—the carved bas-relief, the gilt wall sconces, the cupid’s head above the sink—gave me the sacrilegious feeling of relieving myself in a mausoleum. Clutching the railing, she descends the sort of grand spiral staircase that Vivien Leigh might have been carried up. My father relates that as a boy he once fell all the way down the staircase to land at the carpetless bottom: the last sound he heard before losing consciousness, he claims, was my grandfather calling, ‘Don’t chip the stairs!’

Westchester extends downwards from near Sing Sing towards New York City, fizzling out in the fallen resorts of Yonkers, New Rochelle and Mount Vernon in the south. Once smart summer towns, then nesting grounds for commuters, very white, very WASP, now they’re no longer bedroom communities so much as the maid’s bedroom, the distant highway exits those who take care of the children and mop the floors take to find their way home to sleep at night. The rest of Westchester considers them far too close, in this freeway era, to scary Harlem and the filthy Bronx. The county ends, in the east, with Long Island Sound, not far from Chappaqua. To the west is the Hudson river, where the robber barons used to sail up and down, and later built, as John D. Rockefeller did, their summer homes.

‘God gave me my money,’ John D. famously declared. God hadn’t given my grandfather his money, exactly. In fact my grandfather was a lower-middle-class Russian Jew with a newly anglicized surname and a mother known, even to her children, as ‘Tessie the Terror’. In photographs he is a handsome young buck with a sweet smile and a Mephistophelean glitter in his eyes: the sight of him suggests clichés of the Roaring Twenties, the jalopy chugging to the bootlegger’s, the swallowing of goldfish. As it turned out, however, he had none of the era’s impulsiveness. He’d protected himself from every disaster, even the Depression, by planning ahead.

My grandmother was the oldest daughter of a self-made immigrant German Jewish clothing merchant, or shmata salesman. The clothing merchant opened a store on Union Square, and made a small fortune off an emerging New York middle class of Jews, Italians and Irish too timid to venture into the Episcopalian Abercrombie & Fitch, or the more upmarket Macy’s and Bloomingdale’s. He became famous for his brutal union-busting tactics and his adept use of Pinkerton men. I can only guess that my grandmother was restless. She eloped with my grandfather at sixteen, his first landmark on the road of upward mobility. A bright girl and an ugly one, she knew his proposal was nothing personal.