The Upper East Side of Manhattan, the home of people with more accumulated wealth than anywhere else in the world, began as much of New York City did, as farmland. Its eastern border was established at Fifth Avenue when work began on Central Park in 1857, but most of the area was still farmland when the park was completed in 1873. During the 1880s, the avenues—Fifth, Madison, Park, Lexington, Third, Second, First—were paved, and rich New Yorkers as well as many who had made their money elsewhere, including Pittsburgh steel baron Andrew Carnegie and Montana mining magnate William Clark, built mansions on Fifth Avenue. Third Avenue, with its elevated train line, was lined with walk-ups for working- class commuters, while the side streets off Fifth Avenue were filled with massive brownstones shielded from the industrial haze along the East River. The Upper East Side began taking on its present character in 1913, when Grand Central Terminal was opened and the New York Central rail line was buried under Park Avenue. What had been a filthy railroad cut became a broad boulevard lined with grand apartment buildings. The federal income tax, passed the same year, had the unintended consequence of encouraging New York’s rich to dispense with grand mansions and live, quietly and out of sight, in apartment buildings where doormen protected their privacy. The Upper East Side remains a world apart from ordinary folks. Even as the recession hit in 2008, it set records for the number of $5 million-plus residential sales, and the locals complained about how tough it was to exist on a mere $500,000 annual income—which President Obama set as the top salary for executives in banks receiving federal bailout money.

The emergence of the modern Upper East Side represented yet another iteration of the pattern noticed by the mid-19th-century New York diarists Philip Hone and George Templeton Strong: On such a compact island, it took only a generation or so before buildings were torn down and rebuilt. Even today, New York is being transformed by gleaming postmodern skyscrapers and high-priced storefronts, though its most enduring landmarks were products of the first half of the 20th century: the Flatiron Building, built in 1901; the Woolworth Building and Grand Central, in 1913; the Chrysler Building, in the 1920s; and the Empire State Building and Rockefeller Center, in the 1930s. The United Nations headquarters, the world’s first glass-fronted skyscraper, went up after World War II. This area also holds the more humble distinction of being the site of the first public-housing project in America: The First Houses were built in lower Manhattan in 1935 by Mayor Fiorello LaGuardia.

The 14th Congressional District of New York includes within its irregular borders the Upper East Side and nearly all of these famous buildings. It begins at East 96th Street, the historic dividing line between Manhattan’s wealthiest and poorest neighborhoods, and runs all the way down to East 9th Street in the East Village. It includes all of Central Park, much of the midtown corporate district, Murray Hill in the 30s and Gramercy Park to the south. It takes in parts of the East Village, with its pricey lofts and busy nightlife, and the Lower East Side. Midtown Manhattan’s skyscrapers and the Garment District are also here, as is Roosevelt Island, a 147-acre expanse in the East River that was transformed in the 1970s from a hospital-and-prison complex into an ethnically diverse residential neighborhood (and stripped of its old name, Welfare Island). The 14th also encompasses part of Queens across the East River; blue-collar Long Island City; Steinway, part of historically Irish Sunnyside; and vibrant Greek Astoria, now with many Asians, Latinos and Arabs. The district’s cultural landmarks are among the world’s finest: the Metropolitan Museum of Art, the Guggenheim, the Whitney and the Frick, but also a rising arts cluster in Long Island City with the contemporary-art gallery P.S. 1 and the American Museum of the Moving Image.

The district has always been dominated by its affluent and highly educated voters, leaders in securities, publishing, advertising, entertainment, broadcasting and communications. Historically, they mistrusted the city’s usually Democratic immigrant masses, the politics of Theodore Roosevelt, the old New York Herald Tribune and Henry Luce’s Time magazine. But the attitude of the Manhattan elite was transformed from liberal Republican to leftish Democratic in a way personified by the Silk Stocking district’s most famous politician, John Lindsay. He was elected to Congress in 1958 as a liberal Republican, an advocate of civil liberties and full of mistrust of machine Democrats and unions. In 1965, he was elected mayor of New York and eventually ran up huge debts that led the city to the brink of bankruptcy in 1975. Neighborhoods deteriorated, and the city lost 1 million people in the 1970s. He was succeeded as congressman and ultimately as mayor by Democrat Edward Koch, who managed to clean up the mess he left in the city’s finances, but then alienated the liberal elite by favoring capital punishment, opposing racial quotas and questioning the efficacy of poverty programs. Since then, Republican Mayor Rudolph Giuliani and his successor, Michael Bloomberg, who lives in a town house on East 79th Street, have been cultural liberals on abortion rights, gay rights and gun control. To the national Republican Party of former House Speaker Newt Gingrich in the 1990s and President George W. Bush, who brought the Republican Convention of 2004 to a less-than-enthralled Manhattan, the Upper East Side was unremittingly hostile. When the rest of the country narrowly favored Bush over Democrats Al Gore and John Kerry, the Upper East Side voted for the Democrats by wide margins. The Upper East Side’s 10021 zip code was the nation’s top zip code for Democratic campaign contributions in 2004 and 2008.The district voted for Democrat Barack Obama over Republican John McCain 78% to 21% in 2008.