On a rainy August night in 1962, a group of about a hundred protesters gathered at the corner of Sullivan and Broome Streets in Soho. The weather added a somber air to what was already supposed to be a solemn occasion: a New Orleans-style funeral march through the streets of the neighborhood and then up to the iron fence surrounding Gracie Mansion. The protesters carried signs that read, "Death of a Neighborhood" and "Little Italy—Killed by Progress." Artist Harry Jackson had adorned the signs with tombstones and skulls.

What the marchers had gathered to protest was the Lower Manhattan Expressway, a 10-lane superhighway connecting Long Island to New Jersey. In renderings, LOMEX (as the highway is often known) looks like something out of a dystopian vision of New York’s future, its elevated superstructure slicing through swaths of Little Italy and Soho—neighborhoods that would no longer exist as we know them if it had been built.

The highway was to be a crowning achievement in the career of Robert Moses, the so-called "Master Builder" of New York. At the peak of his career, Moses held 12 diverse city and state government jobs simultaneously. It was Moses’s devotion to the automobile that drove nearly all of his thinking. As he once remarked, "cities are created by and for traffic. A city without traffic is a ghost town." LOMEX was to be the fulfillment of Moses’s vision for a modern, efficient, car-centric New York.

When the marchers reached the block of Broome between Mott and Mulberry, they paused for speeches from local residents, assorted politicians, and the woman behind this effective publicity stunt: Jane Jacobs. The celebrated author of The Death and Life of Great American Cities had already tangled with Moses over Washington Square and the slum designation of her own West Village neighborhood. Armed with grassroots connections and an anti-development playbook, Jacobs was able to shut the expressway down.

But at what cost? In many ways, Soho today doesn’t resemble the neighborhood that Jane Jacobs fought so hard to save.

The idea for a highway in Lower Manhattan dates back to the opening of the Holland Tunnel in 1927; its first year, 8.5 million vehicles used the tunnel, clogging up the narrow streets of Soho (then still a light manufacturing district), Little Italy, and Chinatown.

Two years later, when the Regional Plan Association released its Regional Plan of New York and Its Environs, it called for major improvements to traffic, though it focused more energy on container shipping, trunk-line railroads, and suburban rapid transit than on solving the issues of Manhattan gridlock. For Lower Manhattan, the plan simply suggested an artery extending from the Holland Tunnel "for vehicular traffic...connecting on the east with the Manhattan Bridge to Brooklyn." This was exactly the sort of plan Robert Moses could embrace.

Moses had literally grown up with the car. When he was five years old, the Duryea brothers had road-tested the first American-made auto; by the time Moses started his five-decade career in New York public service in 1919, there were nearly five million cars and trucks registered in the United States. By the time the Regional Plan Association issued its call for more roads in 1929, Moses, who never learned to drive and would come to employ "a staff of chauffeurs on 24-hour call," saw the automobile as the defining characteristic of modern life.

However, Moses, whose biggest job was head of New York State Parks Commission, was not yet in a position to do much about building a highway in Manhattan. The regional plan’s vaguely worded recommendation languished until 1939, when it was put forward again by the City Planning Commission as the Lower Manhattan Crosstown Highway.

In the intervening decade, Moses had vastly expanded his powers. In 1934, he’d been appointed by Mayor Fiorello La Guardia to oversee a consolidated, five-borough New York City Department of Parks and to head the newly created and wide-reaching Triborough Bridge and Tunnel Authority. With Moses now basically in charge of city traffic, the highway seemed inevitable.

The City Planning Commission officially approved the road in 1941, noting:

This is a much-needed crosstown connection between the Manhattan and Williamsburg bridges, and the Holland Tunnel, serving local cross-Manhattan traffic as well as traffic from the bridges and the tunnel. This connection would not only provide additional needed capacity for crosstown traffic, but would also help relieve congestion on north-south streets by minimizing delays at heavily traveled crosstown streets, such as Canal Street.

When the United States entered World War II at the end of the year, Moses included the planned highway in his 1941 National Defense Proposal, making it "a key connection between Long Island and the interstate system." In 1944, the New York State Legislature approved funding, but the project stalled. Moses already had too many other construction projects pending to move the Lower Manhattan Expressway (as it was now called) forward.

Moses's pending projects included the Brooklyn-Queens Expressway and the Brooklyn-Battery Tunnel, the construction of which called for the removal of Castle Clinton in Battery Park. Though Jane Jacobs was not a direct participant in the battle to save this War of 1812 fort, the skirmish proved to be a turning point in public opposition to Moses’s construction projects. If nothing else, it proved that Moses could lose.

After being decommissioned, Castle Clinton had been converted into a theater named Castle Garden (1825), and then subsequently turned into the Castle Garden Emigrant Landing Depot (1855), the precursor to Ellis Island. When the federal government took over immigration duties in 1891, the fort was remodeled by McKim, Mead & White into the New York Aquarium.

In renderings, LOMEX looks like something out of a dystopian vision of New York’s future, its elevated superstructure slicing through swaths of Little Italy and Soho.

To Robert Moses, none of this history mattered. In a lengthy rant published in February 1941 in both The New York Times and the Brooklyn Daily Eagle, Moses criticized the building and the "stuffed shirts" who hoped to save it. Castle Clinton, he wrote, "has no history worth writing about." The fort was "an ugly wart" and a "monstrosity," and after pointing out that it was unsuitable for the aquarium, Moses concluded his screed by reminding readers that the city had already restored "scores of historic structures, monuments and memorials," including Gracie Mansion. The editorial had a valedictory tone: Castle Clinton would soon be rubble, and he’d laid out for posterity his compelling reasons why it needed to go.

Yet Moses could not manage to tear it down.

Moses’s opponents bypassed him, and in 1946, Congress stepped in and declared Castle Clinton a national monument. In a rebuke to Moses, the Secretary of the Interior noted the fort was worth saving as it had "played a significant role in the nation’s history and growth."

Compared to the amount of construction that was still moving forward under Moses’s watch, the preservation of one tiny castle seems insignificant. But just as Jane Jacobs—who would later take Moses to task for banishing the aquarium from Castle Clinton out to Coney Island—began to become enmeshed in issues regarding urban planning and renewal, small victories such as this were a bellwether of things to come.

Jane Jacobs began her career as a freelance writer for magazines such as Vogue and the Sunday Herald Tribune before landing a job writing for the State Department’s publication Amerika during World War II. She met and married her husband while working at the State Department, and they bought a rundown townhouse on Hudson Street in the West Village that they planned to rehab themselves. In the 1950s, she moved to Architectural Forum, where she began tackling issues of urban development, arriving at the magazine during the height of Robert Moses’s efforts to remake the city—including her own backyard. Through observation of her neighborhood and others around the city, Jacobs developed a philosophy of urban planning that clashed with Moses’s. As she would later encapsulate in her book The Death and Life of Great American Cities, Jacobs believed that city planners should focus on preserving neighborhoods as diverse, walkable, mixed-use areas, paying close attention to the intrinsic value of older buildings while shunning car-centric construction.

It’s little wonder that Robert Moses would later characterize the book as both libelous and inaccurate.

In 1952, he had proposed a four-lane roadway through Washington Square linking Fifth Avenue to West Broadway. Shirley Hayes, a nearby resident whose children played in the park, spearheaded a campaign to not only stop this new construction but to remove traffic from the park altogether. In her first direct tangle with Moses, Jane Jacobs joined the fight, and in 1959, Hayes’s Save the Square coalition successfully got all traffic banned from the square. Moses was stunned. "There is nobody against this," he allegedly remarked. "Nobody, nobody, nobody but a bunch of...a bunch of mothers."

In February 1961, just as The Death and Life of Great Americans Cities was about to be published, Moses attacked Jacobs’s neighborhood again by claiming the 14-block area surrounding her Hudson Street home was a "blighted" slum ready to be torn down and redeveloped.

Jacobs, who’d learned the value of publicity and grassroots organizing from the battle over Washington Square, quickly mobilized a Committee to Save the West Village. Hundreds turned out for court hearings and protests, and by September, Mayor Robert Wagner—likely worried about his reelection prospects—asked the City Planning Commission and Robert Moses to abandon their urban renewal of the West Village. By October, the plan was officially dead, and it had taken just eight months to kill it.

In 1955—in the midst of the battle over Washington Square—Robert Moses’s Triborough Bridge and Tunnel Commission had issued a Joint Study of Arterial Facilities that revived plans for the Lower Manhattan Expressway. For the first time, the roadway’s actual path—containing both elevated and sunken areas—was laid out:

East of the Holland Tunnel, the widened right-of-way would follow the north side of Watts Street, continuing eastward as an elevated eight-lane route along the north side of Broome Street. Near Centre Street, the outer lanes of the highway would descend and pass under Elizabeth Street, continuing eastward in an open-walled cut to the Williamsburg Bridge Plaza. All streets except Mulberry and Mott would be carried across bridges over the depressed highway. At Suffolk Street the alignment would meet Delancey Street.

Of the $72 million the commission budgeted for the project, $28 million was for acquiring real estate. Countless historic structures were in the path of the highway, including the renowned Haughwout Building, a cast-iron gem and home of the first commercial elevator. In her book Jane Jacobs: Urban Visionary, author Alice Alexiou notes other significant structures that would have needed to be knocked down, including

the gargantuan domed Italianate Police Department headquarters… [and] Engine Company Number Fifty-Five, a little gem of a firehouse built Renaissance Revival style. LOMEX would have wiped out the pastry shops and restaurants of Little Italy, and then eaten up the lighting and restaurant supply stores clustered in and around the Bowery. Finally, it would cut across Chrystie Street, wiping out the shady park in the street’s center….

None of this bothered Moses. As with Castle Clinton, he saw the positive benefits of the highway far outstripping any loss of architecture. The highway would "encourage improved housing, increased business activity, higher property values, a general rise in the prosperity of the area, and an increase in the real estate tax revenues therefrom." The buildings to be demolished were merely decrepit reminders of old New York. "When you operate in an overbuilt metropolis," Moses remarked, "you have to hack your way with a meat ax." In all, 1,972 families and 804 businesses were set to be displaced by the expressway.

Soon after Jane Jacobs’s victory over Moses in the West Village, Gerard La Mountain, one of the priests at the Church of the Most Holy Crucifix in Soho, came to Jacobs to ask for her help in battling LOMEX. In early 1962, despite not being fully funded, construction was slated to begin on a small section of the highway at the corner of Broome and Chrystie streets. After 33 years of LOMEX existing only as diagrams on paper, this was no longer a hypothetical battle: if Moses wasn’t stopped, entire neighborhoods would be uprooted.

Jacobs quickly formed a Joint Committee to Stop the Lower Manhattan Expressway, pulling other organizations together to oppose the highway, including the Lower East Side Businessmen’s Association, whose unofficial headquarters, Ratner’s, was one of the neighborhood fixtures destined for the wrecking ball. Not only did Jacobs rally people to her mock funeral along Broome Street (or send them to public meetings wearing gas masks to protest the pollution that the highway would rain down on them), she also distributed materials like a lyric sheet for the song, "Listen, Robert Moses," supposedly written by Bob Dylan. Though Dylanologists have questioned his authorship, Jacobs's son Jim has recently confirmed that Dylan came to their house to work with Jacobs on the lyrics. The song encapsulates the frustration of Soho’s residents:

Listen, Robert Moses, listen if you can It’s all about our neighborhood that you’re trying to condemn We aren’t going to sit back and see our homes torn down So take your superhighway and keep it out of town

Subsequent verses talk about the 20-year "shadow" hanging over the area, its residents worried the bulldozers could arrive at any minute to make room both for the highway and subsequent "fancy stores." Little did they know that the fancy stores were coming, highway or no.

Threatened with LOMEX’s "de-mapping" in 1963 due to a lack of money, Robert Moses redoubled his efforts, bringing together good government groups like the Citizens Union to show their support for the highway. In November 1963, a tenement on Broome Street was condemned as "unfit for human habitation." As the New York Times—a strong supporter of the highway—pointed out in its coverage, it was just such buildings that would thankfully be cleared out to make room for LOMEX.

Meanwhile, Porter Flushing Realty Corp., a commercial property owner along the highway’s proposed route, took the city’s planning commission to court, arguing that the city’s indecision about whether or not to start building the highway was devaluing properties. In February 1964, the New York State Supreme Court agreed with the plaintiff, ordering the city to make up its mind about building LOMEX. Even though the state’s appellate court soon overturned that ruling, the highway remained stalled by government inertia.

When John Lindsay was elected mayor in 1965, he inherited both Moses and LOMEX. Though Lindsay had originally been opposed to the highway both as a congressman and as a candidate, he changed his mind, commissioning the architect Shadrach Woods to look into how the plan could move forward without the "expressway [becoming] a scar on the body of the city." Complicating Woods’s planning was the fact that work on the highway would now be constrained by a new wrinkle: the city’s brand-new Landmarks Preservation Commission. Just before Lindsay’s election, the commission had landmarked its first set of properties, including the Haughwout Building, which lay directly in the path of the proposed elevated roadway. Woods eventually recommended making much of the highway a sunken thoroughfare built using cut and cover techniques. This, combined with the inclusion of new housing linked to the highway’s construction, made Woods’s plan more sympathetic both to the residents and the architecture of the area. At the same time, the Ford Foundation commissioned former Yale School of Architecture Dean Paul Rudolph to envision his own possibilities for LOMEX. Following Woods’s lead, Rudolph’s vision included housing, a depressed roadway, and—in a move that Robert Moses surely would not have condoned—public transportation in the form of monorail "people movers."

But neither Woods nor Rudolph’s plans could keep LOMEX alive.

Indeed, despite Moses’s ongoing efforts, for decades the project had essentially been a zombie—seemingly dead, but never buried.

On April 10, 1968, Jane Jacobs found a way to kill it once and for all.

That evening, the New York State Department of Transportation held a public meeting at Seward Park High School on the Lower East Side to inform residents about LOMEX’s progress and to solicit feedback from the community. It was a pro-forma meeting, hastily scheduled so that the state could say it had fulfilled its role of being publicly accountable. As Anthony Flint notes in his book, Wrestling With Moses: How Jane Jacobs Took on New York’s Master Builder and Won, the "ostensible purpose of the meeting was to collect opinions about the project," but the speed with which the affair had been put together was probably to discourage turnout. Instead, a large crowd showed up and—knowing Jacobs was in the audience—began to chant "We want Jane!"

A large crowd showed up and—knowing Jacobs was in the audience—began to chant 'We want Jane!'

When Jacobs finally took the microphone, she addressed the audience, not the officials. "What kind of administration could even consider destroying the homes of two thousand families at a time like this?" she said to cheers. "If the expressway is put through," she added, "there will be anarchy."

Exactly what happened next is unclear—as Flint notes, some claim Jacobs tore up the stenographer’s records so that there would be no official record of the meeting. Certainly, she encouraged other protesters to join her onstage and was ultimately arrested. The police took her down to the station (with many protesters trailing behind) and booked her for disorderly conduct. For hours, supporters stood outside the police precinct chanting, "We want Jane!"

The next day, Jacobs’s arrest made the papers, shedding light on the battle over the expressway in a way that protests and public hearings and letters to the editor never could. With Robert Moses’s power within City Hall waning, John Lindsay withdrew his support for the project in 1969. It was quietly de-mapped in 1972, more than four decades after it had first been proposed. By the following year, when the Soho/Cast Iron Historic District was created, many of the buildings that would have been either destroyed or overshadowed by the highway were individual landmarks, making a revival of the plan impossible.

Throughout her life in New York, Jane Jacobs consistently viewed the sort of change Robert Moses brought to a neighborhood—be it a Title I housing project, a highway, or Lincoln Center—as antithetical to the best interests of the residents of that area. She argued that these developments impeded the diversity of uses and structures that made for vibrant neighborhoods. For example, Jacobs feared that Lincoln Center was being "planned on the idiotic assumption that the natural neighbor of a hall is another hall. Nonsense. The natural neighbors of halls are restaurants, bars, florist shops, studios, music shops, all sorts of interesting places." She never imagined that Lincoln Center might spur the creation of restaurants, bars, and the like.

Similarly, there’s no way to know today what the ultimate effect of LOMEX would have been on Soho and its environs. The idea of a 10-lane elevated highway in Soho and Little Italy seems outlandish today, but it’s easy to forget that in the years immediately following World War II, areas like Soho were seen as symbols of urban blight. Known as "Hell’s Hundred Acres" due to the propensity of the buildings to catch on fire, the area that now boasts some of New York’s priciest real estate was on the verge of being torn down. LOMEX would surely have been the catalyst for the wholesale destruction of the neighborhood so that Moses could start from scratch.

But keeping LOMEX out of the neighborhood didn’t save it. While it is true that much of the architecture was spared, decades of gentrification have seen the area radically transformed into the high-priced residential and retail neighborhood that it is today. That transformation pushed out the very long-term tenants that Jacobs was fighting to protect, and Soho is now chock full of the "higher property values" that Moses craved and the "fancy stores" the former residents feared.

There’s also no way to know what effect Jane Jacobs might have had on the gentrification of Soho had she stayed in New York. Four months prior to her arrest at Seward Park High School, she’d already been arrested for protesting the draft. Following the LOMEX victory, she became determined to move her two draft-age sons out of harm’s way, and the family quickly left for Toronto, Canada. Even when President Carter pardoned American draft dodgers in 1977, the Jacobses chose not to move back to New York, where they would have been returning to a city still in a downward economic trajectory. Jane Jacobs had become enmeshed in battles over development in Toronto, where she stayed until her death in 2006 at age 89. She would never live in her beloved Greenwich Village again.

Soho is now chock full of the 'higher property values' that Moses craved and the 'fancy stores' the former residents feared.

Because Jacobs left New York in 1969, she was not around to fight the increasingly complex preservation battles of later years. Gentrification is a double-edged sword—the preservation of buildings often comes at the expense of people—so it can be tough to practice what Jane Jacobs preached: create new buildings that complement and draw upon the older streetscape in places like Greenwich Village. In New York, the creation of landmark districts—which often preserve buildings that would not normally qualify for individual protection—can stifle economic development, at least in the eyes of some residents and developers. Or such districts can lead to rampant gentrification, rending a neighborhood unaffordable for middle-class New Yorkers. This is, of course, exactly what Jacobs fought against.

And then there’s the traffic issue. As Manhattan Borough President Scott Stringer noted back in 2012, "For residents of the SoHo and Hudson Square communities, horn honking has become the lullaby of lower Broadway." In the subsequent years—with today’s falling oil prices making driving ever more attractive—vehicle traffic has only gotten worse. And with an influx of Financial District residents that neither Jane Jacobs nor Robert Moses could foresee 45 years ago, there’s mounting pressure to find better ways to move people around.

Someday, the Second Avenue Subway will connect all the way downtown, but that will do nothing for all those people trying to get across Manhattan. A congestion tax might keep some of those people off the road, but proposals for such a fee can’t clear the necessary hurdles in Albany. Though it seems impossible that it would ever get revived, one could consider a scaled-down version of LOMEX—perhaps an elevated highway over Canal Street shuttling traffic from the Williamsburg Bridge to the Holland Tunnel.

Robert Moses dreamed of a modern city of traffic and skyscrapers. Jane Jacobs argued for the possibilities of tight-knit neighborhoods of brownstones and mixed-use buildings. Perhaps we are lucky that the Manhattan of the 21st century is an uneasy truce between these two seemingly divergent points of view, an ongoing dialogue between the need to preserve the past and build the future.

Editor: Sara Polsky