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The Outer Borough

Staten Island has long been demeaned as a provincial punch line. But flashy, independent, and unapologetically outré, it's one of the last brash outposts in an increasingly prim city.

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Joann Dapolito and I leave High Society, the hair salon she owns on the corner of Old Town Road and Hylan Boulevard on Staten Island, and we hop into her cream-colored Jaguar XJ8 Sport. She's wearing sleek black bell-bottom slacks, patent-leather boots, and a tight wool sweater with removable sleeves. "I got this on 86th Street in Brooklyn," she tells me about the sweater. "I shop there a lot, and I go to the Short Hills Mall in Jersey and Paramus Mall, too." Joann is my second cousin. We're both 38, and we grew up near one another on Staten Island. But we haven't hung out together since I ran away about fifteen years ago. Making the break wasn't easy. If I felt I wasn't accepted on sleepy and often inflexible Staten Island because I was gay, I certainly felt I wasn't accepted in Manhattan because, well, I was from Staten Island.

These days it's the Manhattanites who are heading for Staten Island. Saint George, the once-declining old section where the ferry lands, is becoming what Estelle Karp, a Century 21 realtor on Victory Boulevard calls "a new renaissance area," as the double latte set discovers the city's final frontier. "A lot of people are getting priced out of Manhattan," she reports. "They're buying up the old Vanderbilt Victorians that were playgrounds for the rich of that era. It's only going to intensify with the new ferry terminal being built, lots of shops and walkways, and the new minor-league Yankees' stadium."

But there's a cultural gulf 10,000 miles wide separating trendy urban Saint George and the rest of Staten Island -- the Staten Island Joann and I are driving through. Soon enough, we're whirling up exclusive Grymes Hill, heading toward a gated community known as the Enclave, where Joann lives with her husband, Paulie, and their two children, Ashley, 8, and Paul IV, 5, in a house with seven bathrooms on a cliff overlooking New York Harbor and the Narrows.

Paulie is a quintessential Staten Island success story. Like a lot of young guys from Brooklyn, Queens, and Staten Island, he decided against college and went to work on the floor of the New York Commodities Exchange at the age of 18, hoping to make it big. Whether they be secretaries or stock traders, Staten Islanders have always preferred to work in lower Manhattan -- a brief, free ferry ride away. When I was in high school, working part-time in the mail room at the AT&T building on Sixth Avenue just south of Canal Street, people in my neighborhood couldn't believe I was working so far "uptown."

Wall Street is also popular because it offers opportunities to make big money without having to spend those four years earning a college degree. On Staten Island, making money, and doing it quickly, is what counts most.

"My cousin knew all the people on the trading floor, so I began working there," Paulie says, explaining his upward trajectory. "At first I didn't care whether I was there or in outer space. I mean, it was 1979, and I was 18. But within three months, I caught on to what was really going on. I was hanging out with guys who were going to champagne lounges, drinking the best. Rolls-Royces, limousines, the works. I was like, 'Something's really good about this business.' I caught on to it. In a year I was on my way to making that my career." He eventually opened his own commodities firm with his brother and his cousin, trading cocoa futures. Today his company, Dapco, is the biggest firm trading cocoa futures on the exchange. "But now I'm looking for something else," he says, anticipating a market downturn. "I'm thinking about construction."

Joann is a Staten Island success story of her own. Well-off Islanders who don't work on Wall Street tend to be private-business owners -- like Joann's father and my father, both of whom started out in the restaurant business, without the college detour -- rather than, say, doctors and lawyers. Joann opened High Society in 1980, after getting her degree in haircutting from the Wilfred Academy. And the business took off.

Joann and Paulie moved to the house in the Enclave in 1997, from Prince's Bay, where they had "a regular, half-million-dollar house," says Joann. The Enclave was once the site of the gargantuan Hormann Castle, built in 1891 by a German industrialist and torn down in 1968. Now, nine homes, each worth well over $1.5 million, are perched atop a steep slope there. Unlike the rest of New York City, Staten Island is distinguished by seven very high, mansion-laden hills that dot the middle of the island from north to south, including Lighthouse Hill, where a 100-year-old lighthouse surreally sits not far from a Buddhist temple that houses the largest collection of Tibetan art in the Western hemisphere (the Jacques Marchais Museum of Tibetan Art); Emerson Hill, where Ralph Waldo Emerson lived during his heyday; and Todt Hill (todt is Dutch for "death"), whose residents have included many reputed mobsters.


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