Dana Goldstein is a journalist based in New York City, and author of the New York Times best-seller The Teacher Wars: A History of America’s Most Embattled Profession.

On a hot Thursday afternoon in August, Tatlin McLeod sat on a shaded bench at the Chappaqua train station, sipping an iced drink out of a takeout cup. McLeod lives in the Bronx and commutes to this Westchester County suburb, 35 miles north of Midtown Manhattan. She has been working as a nanny for various Chappaqua families for 13 years. She is black and an immigrant from Jamaica.

Tucked into a set of forested hills, Chappaqua is a hamlet of 1,400 residents, famous as the adopted home of Bill and Hillary Clinton. I grew up in a neighboring village called Ossining, but to me, Chappaqua has always seemed a world apart; almost like the movie set version of a 19th century American suburb. Stately colonials and Victorians are situated on large plots, nary a McMansion in sight. (The Clintons live on a street called Old House Lane.) Many residents can walk from their homes to the train station, where there is an upscale restaurant and coffee shop. Property values reflect the fact that the public schools in Chappaqua are considered some of the best in the nation. The average home price here is more than $840,000, compared with $340,000 in Ossining.


As we waited for the train, I asked McLeod whether she would ever want to live in Chappaqua instead of commuting back and forth. She shrugged as if it were a moot point. “It’s too expensive,” she said.

Housing segregation is one of the great unsolved policy crises in American life, driving a sharp wedge between the nation’s haves and have-nots—those who get the opportunities afforded by living in prosperous towns like Chappaqua, and those who never could. Seven years ago, it seemed that Hillary Clinton’s hometown might willingly lead the way in changing this. The Obama administration joined a lawsuit brought by the activist Anti-Discrimination Center alleging that Westchester County had willfully violated the Fair Housing Act by not exploring the ways communities make it difficult to build affordable housing. The county agreed to a landmark settlement that the Obama administration once hoped would be a template for the nation. Westchester agreed to construct 750 units of affordable housing in 31 majority white and affluent towns, including Chappaqua.

As of last year, only 334 new affordable units were occupied in Westchester, none in Chappaqua. The plan isn’t dead—several hundred units are still being developed across the county, including a potential 63 in Chappaqua—but even if they’re all built, it remains a drop in the bucket in a county of nearly a million people; a report from Rutgers University estimated Westchester would need at least 10,768 new affordable homes to satisfy demand.

New affordable housing has become a third rail in local politics. Politicians here have run—and won—on the promise of fighting the zoning changes that could lead to more and faster construction. In Chappaqua in 2013, the town council approved a plan for a politically connected developer, Conifer Realty, to construct an apartment building of 28 units, all reserved for renters earning less than $64,000 per year. It is supposed to be built on Hunts Lane, a mile-and-a-half from the Clinton home and just a few hundred feet from where Tatlin McLeod and I were sitting at the train station, on the other side of the Metro-North tracks. Most of the officials who made that deal lost their seats.

Today, the site remains an empty lot, overgrown with weeds. I gestured toward it, and asked McLeod what she thought of putting an affordable apartment building there. She scoffed. “They will vote it down, knowing these people,” she said. I asked whether she thought the residents of Chappaqua didn’t want black neighbors. She shook her head no—she didn’t think this was about race. “My bosses are really nice,” she added. But Chappaqua is for people with money, she told me. Some folks hated the fact that there was a Dunkin’ Donuts in town, McLeod said; the chain was too downscale. She displayed her iced drink. “Some of them can be so cocky.”



What’s happened in Chappaqua shows just how complicated the politics of American housing are.



What’s happened in Chappaqua, and in Westchester more broadly, shows just how complicated the politics of American housing are—and how intractable the issue has become. Where a family lives shapes a child’s academic outcomes, his likelihood of getting arrested and his income as an adult. American suburbs—though more racially diverse today than ever—are internally segregated, with low-income and nonwhite families living in communities with fewer white residents and lower-performing schools. In principle, even the neighbors here approve of trying to rectify this problem. Many in this Democratic-leaning town say they welcome more affordable housing and more diverse neighbors. Under legal scrutiny from the federal government, the town council, in April, allowed the Hunts Lane development to move forward. Yet the project still remains caught in red tape: It needs to be approved by New York State, and local officials and a media-savvy group of activists remain vocal critics. Robert Greenstein was elected town supervisor in 2013. He is a registered Democrat who ran on the Republican ticket, in part to oppose the development, which he says is poorly located—too close to the train tracks and too far away from Chappaqua’s established residential neighborhoods. “I think affordable housing is a noble goal,” he said. “I like the idea that a certain amount of units should be affordable. What I don’t like is forcing municipalities to build affordable housing. I don’t think it’s fair.”

He continued, “Let the market work the way it works. In our town, there’s no discrimination. It all comes down to money. Whether you can afford it or not. The only color that matters is the color of your money.”

***

In the popular imagination, Westchester might be the quintessential white American suburb, land of John Cheever and Don Draper. Yet in reality, 40 percent of Westchester residents are black and Latino, and 10 percent are from low-income households. Their families, however, are clustered. At Horace Greeley High, the public school in Chappaqua, just 6 percent of students are black or Latino and 4 percent live in poverty. Fifteen minutes away at Ossining High School, my alma mater, 64 percent of students are black or Latino and 49 percent are from low-income households.

This micro-segregation shapes lives. An emerging body of social science suggests that for low-income families, having the freedom to move is much more powerful than previously acknowledged. Last year, Harvard economists Raj Chetty, Nathaniel Hendren and Lawrence Katz reassessed data from Moving to Opportunity, a federal experiment to move poor families into neighborhoods where fewer than 10 percent of residents were from low-income households. It had long been clear that older teenagers struggled when their families moved and left behind established social networks. But the economists decided to isolate those children who were youngest—under the age of 13—when their parents moved. As adults, those children earned 31 percent more than peers who never left low-income, segregated areas.

These findings point toward some of the shortcomings of social policy over the past two decades. Consider education reform: President George W. Bush’s No Child Left Behind law, Obama’s push to improve teacher evaluation, and the charter school movement were all built around the idea that racially segregated, high-poverty schools, if held accountable, could achieve the same results as affluent schools, setting poor children on a better life trajectory. But social science shows that schools and teachers have less of an impact on children than do parents, neighborhoods and peers. The future of the fight against intergenerational poverty may have less to do with accountability, the bipartisan catchphrase of the early 21st century, and more to do with integrating poor children of color as both neighbors and classmates, with their middle-class, affluent and white peers. To that end, Obama is ending his second term with efforts to desegregate both housing and schools. But integration forces affluent white people to do something big: accept newcomers into their communities.

The fight in Hillary Clinton’s hometown shows how tough that can be politically. In 2009, federal judge Denise Cote ruled that Westchester County’s fair housing reports to Washington were “false and fraudulent,” as they did not accurately convey barriers that nonwhite and poor families faced in finding housing in the region. For decades, Westchester had clustered most of its federally subsidized affordable housing within just a few towns and cities that already had significant black and Latino populations, like Yonkers, White Plains and Mt. Vernon. Communities like Chappaqua, its parent town of New Castle (where New York Governor Andrew Cuomo lives) and Briarcliff (where Donald Trump owns a golf course) remain overwhelmingly white and rich. According to the legal settlement between Westchester and the Obama administration, that would have to change.

The federal settlement didn’t go unnoticed at the polls. Many of the Democrats who agreed to the settlement were voted out. A conservative talk radio producer and host named Rob Astorino ascended as county executive in 2010. He promised to resist the housing agreement, which he talks about as a threat to “home rule.” When Astorino ran for reelection in 2013, one of his campaign posters featured two single-family homes dwarfed by an apartment building, under a dark, menacing sky. “Don’t Let the Federal Government INVADE Tarrytown,” it read. In a county where less than a quarter of voters are registered Republicans, Astorino won handily with 56 percent of the vote.

Westchester County Executive Rob Astorino greets a member of the congregation at the Shiloh Baptist Church in New Rochelle, New York, on Nov. 2, 2014. | AP Photo

Despite the political fallout, there has been some progress. As part of the agreement, 15 Westchester jurisdictions, including New Castle, rewrote zoning codes to require developers of future apartment buildings to set aside 10 percent of units as affordable. But very little changes when a town promises to set aside affordable units in future apartment buildings if it is next to impossible to construct apartment buildings in the first place.

According to a report by demographer Andrew Beveridge of CUNY, in Westchester towns like Chappaqua less than 5 percent of land is used for multifamily housing. Building in Westchester can be difficult because of environmental concerns; New York City drinking water flows through the county, and the state places stringent restrictions on water use and the construction of sewage and septic systems. But experts who have studied the region agree that segregation there is also driven by zoning laws that restrict the construction of multistory, multiunit buildings—the types of buildings that low-income people of color, as well as many retirees and young professionals, can afford and often prefer.

“Exclusionary zoning has caused a tremendous shortage of supply,” said Alexander Roberts, executive director of the advocacy group Community Housing Innovations. “Exclusionary zoning sabotages the free market, in that government regulation dictates supply and demand.”

For example, in Chappaqua and its parent town of New Castle, the zoning code calls for each apartment in a multifamily building to have a separate entrance and exit to the outside, to promote “safety and the avoidance of common hallway areas.” Any developer that wishes to build a more conventional apartment building must seek special permission from the town.

Zoning laws date to the early 20th century, when they were used to protect urbanites from living next to dirty, unhealthy industrial sites. But when white families began moving to the suburbs en masse in the 1950s—aided by mortgages denied to black families of similar wealth—zoning took on a more ideological cast. There was “anti-Communist hysteria,” said Douglas Massey, a Princeton University sociologist who focuses on housing segregation. Policymakers wanted “to turn the mass of Americans into property owners, and give them a house and lawn and make them think they were lords of their manor. They saw high-density housing as socialist.” Then, in the 1960s, as crime rates rose, high-rise urban apartment buildings became associated with violence and drugs. “White suburbanites have never wanted poor, dark people in their communities,” Massey said.

The Fair Housing Act of 1968 was intended to counter those biases, by outlawing the refusal to finance, sell or rent to minority groups. But for almost a half-century, there was ambiguity over how suburban zoning laws—which create segregation without being explicitly racially targeted—should be addressed.

Last year, the Obama administration published a new regulation known as the Affirmatively Furthering Fair Housing Rule. It essentially enshrines the principles of the Westchester settlement, stating that municipal recipients of federal housing funding must analyze whether local zoning laws prevent the construction of affordable housing within higher income neighborhoods, and then work to rewrite those laws. If jurisdictions fail to do so, they risk losing federal funds. In September, the White House released a Housing Development Toolkit, intended to guide cities and towns on fair housing requirements.



Conservative media have responded by alleging that Obama’s waging a “war on the suburbs.”



Conservatives have responded with outrage. Breitbart.com and the New York Post have railed against Obama’s “war on the suburbs.” In Congress, Representative Paul Gosar (R-Arizona) introduced a bill that would prevent the administration from implementing the Affirmatively Furthering Fair Housing Rule. Astorino, the Westchester County executive, applauds that effort, and has frequently appeared on Fox News to discuss his opposition to Obama’s housing policies. After an unsuccessful 2014 run against incumbent Governor Cuomo, Astorino has said he is interested in another gubernatorial campaign in 2018. Housing “home rule” would likely be one of his signature issues.

Last year, Astorino staged a news conference outside Clinton’s Chappaqua home, demanding that she comment on the dispute between Westchester and the Obama administration. Clinton did not come out of the house and has never made a public statement on the affordable housing settlement. Her campaign declined my request for a comment on the Westchester case and how it affects the candidate’s hometown of Chappaqua. In a September 21 New York Times op-ed, Clinton wrote about the need for “a national commitment to create more affordable housing” in high-cost areas. She suggested expanding the Low-Income Housing Tax Credit program, which subsidizes development, but does nothing to address zoning restrictions.

Astorino said, “She has a fundamental question she’s failed to answer: If she thinks that the town she lives in and the county she lives in is discriminatory, then why does she choose to live here?”



“If [Hillary Clinton] thinks that the town she lives in and the county she lives in is discriminatory, then why does she choose to live here?” asks Astorino.



He continued, “I’ve personally spoken to Donald Trump about this issue. … The Affirmatively Furthering Fair Housing Rule is absolutely an attack on suburbia.” He accused the Obama administration of throwing “racial bombs. ... What we try to do on the ground is work with our communities and developers and local church groups to actually build housing. That’s how we get it done. I despise the fact that the federal government thinks that nothing can get done without them doing it.” He pointed to new affordable apartments in downtown White Plains, and said he was proud that towns like Port Chester and Sleepy Hollow are affordable, majority Latino communities.

The federal government and Astorino’s administration agree that Westchester is well on its way to financing and building the 750 affordable homes required by the legal settlement—especially if the Chappaqua project is allowed to move forward. But there is a protracted dispute over to what extent the county, as the recipient of Housing and Urban Development grants, should pressure local towns to change their zoning codes. The Astorino administration has submitted several reports to HUD claiming there is no exclusionary zoning in Westchester. The U.S. Court of Appeals for the 2nd Circuit ruled that “the County's conclusion ... is not supported by its own data.” At a July 8 hearing in the case, Judge Cote stated that due to Westchester “abandoning the process” of analyzing impediments to affordable housing, “opportunities were lost both for its citizenry and others who would like to live in the community. And that’s sad. Beyond sad. I could use other adjectives.”

***

Astorino actually supports the construction of the middle-income Hunts Place apartment building in Chappaqua, which could help Westchester get out from under the federal settlement. Perhaps surprisingly, Craig Gurian, the activist housing lawyer who brought the original lawsuit against the county, opposes the Hunts Place building, saying it is too far from Chappaqua’s more exclusive, single-family neighborhoods. “It’s all nice and separated from the white people,” Gurian complained.

Other liberals are skeptical, too. I visited the Hunts Place site with six members of an organization called Chappaqua for Responsible Affordable Housing. They are trying to prevent construction here, and are asking the developer to consider a location closer to a police station, library and elementary school. My guides were all middle-aged or older white men. Their leader, Bill Spade, is a local architect who volunteers for Habitat for Humanity. Ed Frank, an engineer, describes himself as a Bernie Sanders supporter. Will Wedge, a construction manager, has a Planned Parenthood bumper sticker on his car.

“None of us are against the concept of 28 units of affordable housing,” Wedge told me. Bringing low-income families into Chappaqua would mean “subsidizing the morally right thing, which is kids getting access to this school system.”

But what he and the other activists are against, they said, is this particular proposed apartment building. The triangular site is wedged between the train tracks and a highway entrance ramp, and thus would be a dangerous place for children to play, they said. One hundred percent of the units in this building would be earmarked as affordable, which, in an affluent town, could be stigmatizing to the building’s eventual residents, they pointed out. Some of the men are worried about whether residents of the new building would pay their fair share of taxes into the town’s coffers.

Spade, the architect, is working pro bono with Habitat for Humanity to convert a former Quaker meeting house built in 1885—farther from the train tracks—into several three-bedroom apartments whose mortgages will be subsidized for middle-income owners. “This is the ideal way to produce affordable housing,” Spade said. He also supports another project underway in town, in which the defunct headquarters of Reader’s Digest, constructed in 1939, is being converted into a mixed-income apartment building. “I still think there’s a character here that’s worth preserving,” Spade said. “A five- or six-story apartment building? I’d prefer not.”

But are activists making the perfect (aesthetically beautiful, ideally integrated affordable housing) the enemy of the good (more apartments for more people in better school districts sooner)? Holly Leicht, regional administrator at HUD, has been working with Westchester towns to remove barriers to affordable housing. She notes many teachers can’t afford to live in the upscale suburban communities in which they work. Leicht supports the Hunts Place building. “As someone who has seen affordable housing built in a lot of places, I look at that site and I think it seems like a pretty good site. You can walk to the train. It’s a five-minute walk to downtown. ... I am without a doubt that when the project is completed and they do the lottery, it will be overwhelmed.”

Town Supervisor Robert Greenstein agrees that the building will be popular if it ever gets built. “Quite honestly, as bad as I think the location is, I think the people who decide to live there so their kids can get this education are making a good decision,” Greenstein said. “As a parent, I would live on top of the railroad tracks. I think they absolutely are going to be happy living there.”

Westchester County has until the end of this year to prove to the courts that it is not only actively constructing affordable homes, but also identifying and fighting broader barriers to housing choice, like zoning restrictions. The Obama administration has already withheld tens of millions of dollars of the county’s housing funds, and U.S. Attorney Preet Bharara has threatened to hold Westchester County in contempt of court for failing to faithfully execute the settlement. If Judge Cote decides that local zoning remains a barrier, she could compel Astorino to sue his own towns and villages. Astorino likens that option to “dropping bombs on communities.” It could get ugly, and it would take a committed executive branch to pursue a fight with Westchester and other suburbs, which are home to some of the nation’s richest liberals and most influential swing voters. Would Hillary Clinton take on her own hometown? So far, she hasn’t said.