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Times Square Good, Times Square Bad

Nicole Gelinas

July 18, 2024

A new book explains how New York remade Times Square before the turn of the millennium — and reveals its potential re-unmaking.

A new book explains how New York remade Times Square before the turn of the millennium — and reveals its potential re-unmaking.

Preply, the online language-learning company, has bad news for Times Square: The firm’s survey called it “the world’s most stressful tourist trap,” with reviewers condemning the crossroads of the world as “underrated” and “overwhelming.” This May, a resident of a nearby homeless shelter randomly stabbed a female tourist in the chest at Eighth Avenue and 43rd Street, one of a number of unprovoked attacks since an upsurge in violence that began in 2020. This June, a 22-year-old woman was stabbed to death just feet from the New York Times headquarters; in July, a resident of an area supportive housing facility stabbed another tenant to death. Things could be better. They could also be much worse, as Lynne Sagalyn’s lively and well-illustrated “Times Square Remade” reminds us. Which way will things go? “Times Square Remade” offers five lessons — and a warning — for today. 

Sagalyn is New York’s premier redevelopment historian. A now-retired Columbia Business School real estate professor, her previous tome, “Power At Ground Zero,” unspooled the decade-long saga of rebuilding lower Manhattan after 9/11, and she wrote an earlier book about Times Square, “Times Square Roulette.”

The earlier book focused on the intricacies of the government-led redevelopment of Times Square beginning in the mid-1980s. Over close to two decades, New York State and City denuded Times Square of its porno theaters, sex shops and “pross hotels” by using the state’s eminent-domain power to declare 42nd Street from the Broadway and Seventh Avenue bowtie west to Eighth Avenue as blighted. The City, broke after the 1970s financial crisis, funded redevelopment by auctioning the rights to build four skyscrapers at the crossroads to private investors, conjuring money out of the sky by allowing developers to build more densely than they could have — “enormous densities piled high on relatively small sites,” Sagalyn reminds us in the new book. The developers paid up-front, funding the City’s property condemnations. The City has repaid them over the ensuing decades via credits against their property taxes. 

The City used much of the developer windfall to fund 42nd Street’s less profitable cultural rejuvenation, including subsidizing theater and entertainment. The New Victory Theater, the skin-flick-house-turned-children’s-theater, reopened in 1995; “The Lion King” came to the New Amsterdam Theatre two years later; and Four Times Square, the first of the four office towers, opened in 1999. Two commercial multiplex first-run movie theaters anchored the west end of Eighth Avenue, across the street from each other, a symbolic and real victory over the years of on-screen flesh peddling.

The redevelopment has always had detractors. Times Square’s office towers are bad design: like the buildings that anchor the World Trade Center site, or Hudson Yards, they’re non-descript glass shapes. The towers are corporate welfare: The city gave away a lot in the 1980s; developers even wriggled out of a commitment to renovate the subway station. Former redevelopment official (and my former colleague) Bill Stern argued that the City could have achieved the same public-safety and economic-development result without the huge new towers — through preventative policing, broader tax cuts or credits, and zoning to outlaw sex shops — while somehow still respecting the Constitutional right to speech.

Rather than revive bickering over unknowable alternative paths, though, Sagalyn’s book offers a more constructive takeaway: it would have been better for New York not to get to the point where it had to declare the central part of its city blighted and take full control. So why did that happen — and what does that mean for a post-COVID Times Square and New York?

Times Square’s office towers are bad design: like the buildings that anchor the World Trade Center site, or Hudson Yards, they’re non-descript glass shapes.

Lesson one: “Adaptive reuse” is not always a good thing. “Adaptive reuse” — which means repurposing old buildings and infrastructure — is a shibboleth urban-planning phrase, wielded with increasing frequency in the post-COVID planning era. Don’t know what to do with that 11% retail vacancy rate (double that rate in some Midtown areas)? The market will adaptably reuse it for something else!

As Sagalyn writes, 20th-century Times Square was “built on speculation.” Developers speculated that the area would become an office hub. The Times Tower, opened in 1902, was a promising start. But Times Square was too far west of the Grand Central suburban commuting terminal, which opened in 1913, and so that process would take a while, until East Midtown was fully built, and office towers began marching west. 

In the meantime, Times Square thrived as an entertainment mecca. Impresarios such as Oscar Hammerstein knew that “what tourists wanted was not always the uplifting art museums, historical monuments, and public parks, but the satisfaction of good plays, enjoyable food, jolly rides about town, … and live music and entertainment at nightclubs and roof gardens,” as Sagalyn describes.

Developers, as ever, overreached. By 1928, 76 houses offered live performances or movies. But live theater never recovered from the Great Depression. For a while, demand for movies and spectacle filled the gap. 

By the 1950s, though, Times Square felt cheap, with storefronts filled in by “nuisance establishments — freak shows, wax museums, shooting galleries.” But it was a wholesome cheap: “edgy, but …not yet terribly dangerous” or sordid.

As the decades passed and TV and suburban movie theaters and malls competed with Times Square, tenant after tenant left. Times Square’s property owners didn’t leave their theaters and storefronts empty because they couldn’t find a new tenant like the old one. Instead, they adaptively reused them — or allowed new tenants to do so — by turning them into the porn theaters, peep shows and tourist-trap electronics stores that defined the 1970s and 1980s. 

Lesson two: Private profits don’t guarantee a public good. It would have been one thing if this adaptive reuse turned out to be less profitable than earlier uses; real-estate owners would have had an incentive to revert to a better use, and to demand better policing from the city to safeguard quality of life. 

Instead, the odd thing about the Times Square of the 1970s and 1980s — and an obstacle to redevelopment — was that it wasn’t a market failure. It was a small-business success. Elected officials often romanticize small property owners and mom-and-pop entrepreneurs, but a critical mass of small Times Square property owners (and big ones), as well as entrepreneurs, were happy to hawk sex — or, if they weren’t happy, didn’t let their unhappiness interfere with their businesses. For some of the people who came to Times Square to patronize these businesses, including perfectly respectable suburban white-collar commuters, the illegal street activity that ruined the quality of life and public safety for everyone else — drugs for sale, sex for sale — was the attraction. 

The odd thing about the Times Square of the 1970s and 1980s — and an obstacle to redevelopment — was that it wasn’t a market failure. It was a small-business success.

One example of a flexible owner was the mid-century developer Irving Maidman. In 1960, as Sagalyn recounts, Maidman had visions of elevating Times Square, opening four “legitimate” theaters. When his venture failed, he tried to find socially positive uses for his properties, advertising them as arthouse venues or sites for “musical comedy presentations.” By the early 1970s, though, his theaters were running sex shows. Similarly, a few blocks north, Maidman’s Lark Hotel became a “pross” hotel, essentially a brothel. Maidman and fellow property owners could plausibly deny that they condoned or even allowed this activity. Maidman leased the hotel, for instance, to two brothers who “in turn leased to another [party] who was fronting for yet another who held the operating license on the pross hotel. The chain of ownership and leasehold interests aimed to confuse.” 

Lesson three: Social uses don’t guarantee a public good. Local government could have served as a counterbalance to the market’s turn toward the sex and drugs trade. Instead, City Hall acted pro-cyclically, not counter-cyclically, exacerbating Times Square’s downturn. With fewer people staying in Times Square hotels built for middle-class travelers, the City solved this problem by simultaneously solving another problem: where to shelter families who joined New York’s welfare rolls starting in the 1970s. Previously respectable, if shabby, properties, from the Carter Hotel to the Holland Hotel, built in 1919 “as an elegant residence for young women,” became city-subsidized welfare hotels, whose disproportionately dysfunctional, idle tenants further attracted drug dealers and pimps.

Lesson four: Policing wouldn’t have fixed all these problems — but it could have helped. Sagalyn minimizes policing’s potential role. As she notes, by the late 1970s, “Forty-second Street … recorded more than twice as many criminal complaints as any other street in the precinct, with dangerous drugs, grand larceny, robbery and assault topping the list” despite “the greatest concentration of law enforcement officers.” She argues that the fact that this policing ostensibly failed means that policing wasn’t a solution to Times Square. Even with extra police in the area starting in 1978, law enforcement was “of limited efficacy because constitutional safeguards and judicial practices constrained police efforts to control street traffic in drugs, remove alcoholics and vagrants and prevent loitering.” Conclusion: “for more than 40 years, each and every approach — policing, licensing laws, anti-sleaze legislation, anti-loitering laws” and others — “had failed to alter the depth of depravity that infested the Deuce.”

Sagalyn’s argument is that by shuttering 42nd Street’s porn shops and theaters after its efforts at policing failed, the City cut crime even before it built anything to replace the closed storefronts. As she describes the August 1992 scene, “crime dropped so fast it was stunning” after “the state secured title to 34 properties occupied by 250 businesses and a few resident individuals.” Yes, shutting sex-based businesses did decrease sex-based and drug-based crime — between 1990 and 1993, serious crime in Midtown South fell by 31%. Crime also declined citywide for the first time in two decades, as Mayor David Dinkins added police officers and the City moved toward data-driven policing. 

Even as Times Square redevelopment stalled until the late 1990s, crime in Midtown South continued to fall, with felonies down 51% between 1993 and 1998, neatly tracking the drop citywide.

But when Sagalyn says that policing had tried and failed to fix the problems, she’s referring to ineffective, reactive 1970s- and 1980s-style policing: responding to crimes or engaging in high-profile stings that achieved few long-term results. Police arrested small-fry prostitutes and drug dealers, but they were on the street again in days. As Stern has noted, the Midtown South police precinct did experiment with quality-of-life policing in the mid-1980s and saw promising results: a 12% crime drop from 1984 to 1991. But without broader city support, it wasn’t enough.

Moreover, even as Times Square redevelopment stalled until the late 1990s, crime in Midtown South continued to fall, with felonies down 51% between 1993 and 1998, neatly tracking the drop citywide. A more comprehensive lesson is that both physical reinvestments, as well as policing and prosecution, were necessary; throughout the city, Mayor Ed Koch substantially rebuilt the South Bronx beginning in the mid-1980s, and middle-class New Yorkers began renovating brownstones from Harlem to Park Slope. One would not have worked without the other.

Lesson five. Times Square might have withstood any one of these negative forces, but not all of them. Times Square might have recovered from the desertion of its first-run movie theaters and “legitimate” storefronts had the porn industry not been instantly so lucrative for property owners. Unlike many downtowns, New York never lost a mass of commuters to Midtown — commuters who might have patronized ordinary shops that could have rented storefronts at cheaper prices. New York might have lessened the impact of the lucrative sex industry on Midtown if, at the same time, city government wasn’t flooding the area with welfare hotel tenants — or if, at the same time, city government was making life difficult for the porn business by applying preventative policing to the illegal activities — drugs and sex trafficking — that spilled from those businesses. 

But Times Square couldn’t survive the quadruple whammy of the transformation of its legitimate entertainment venues into cash-cow sex shops at the same time as it flooded the area with dysfunctional welfare tenants and had no consistent strategy for policing and prosecution.

Like the city overall, Times Square has lost a decade and a half’s worth of the previous 30 years’ progress in cutting serious crime.

What does this portend? 

The echoes between yesterday’s Times Square and today’s are almost deafening. Today’s editions of porn shops are the cash-only marijuana shops that have colonized many storefronts on Eighth Avenue and even on Broadway, stores that attract harder drug dealers hanging about outside and also attract robbers and thieves; after two years of complaints, the City, under a new state-law framework, is only just now shuttering these shops. Today’s version of welfare hotels is the City’s inexplicable decision, at Times Square’s most fragile moment since the 1960s, to convert thousands of area hotel rooms, including The Row on 8th Avenue, as well as the Candler Building, one of Times Square’s oldest office buildings, into shelters for migrants, including young men who have nothing to do but hang out on the streets. Some of these young men and the people who come to visit them have repeatedly stolen goods from area stores, including a shoplifting case earlier this year that escalated to a tourist being shot. Migrant hotels have welcomed crime-prone transients just as the city is undergoing an experiment in State-driven and DA-driven criminal justice “reform,” reforms that retard the police department’s ability to engage in quality-of-life and broken-windows policing. 

Early results are dispiriting. Through the first half (plus two weeks) of 2024, the 1,831 felony crimes in Midtown South, though down from the 2022 post-COVID peak of 2,142, were 43% above 2019 levels. Like the city overall, Times Square has lost a decade and a half’s worth of the previous 30 years’ progress in cutting serious crime.

No, the City’s failure to learn from its past mistakes doesn’t mean we’re heading back to 1970. But letting the area deteriorate back then until the only option was to nuke it carried a long-term cost. As Sagalyn reminds us, “gone too” in the redevelopment program, along with the porn shops, “were most of the old-time businesses, bars and grills, boxing clubs, and other second-floor activities,” the good condemned along with the bad. Wholesale obliteration hastened Times Square’s transformation into chain-store monoculture, one of the reasons tourists get bored there. 

More practically, we might not have the option of destroying Times Square to save it anew. The millennial redevelopment plan was a microcosm of New York’s overall economic strategy of the past two-thirds of a century: encourage the construction of hyperdense class-A office buildings and then milk them and their income-tax-paying businesses and commuters for money to fund social, public and cultural services. 

But today’s version of the overbuilt theaters and entertainment palaces of mid-twentieth century Times Square is … overbuilt office space, with a 20% Manhattan vacancy rate. Class-A tenants don’t want to be in Times Square today for the same reason they didn’t in the early twentieth century: it’s far away from Grand Central, and it is an entertainment district, complete with Elmo (Sagalyn has nearly a whole chapter on Elmo and his discontents). With East Midtown rezoned for higher office buildings and Hudson Yards beckoning to the west, Class A tenants have their choice. (Yes, Hudson Yards is also far from Grand Central, but, for now, it has the lure of the shiny and new.) It’s not clear, either, that demand exists to continue to sustain two first-run movie theaters on 42nd Street and 8th Avenue, especially as the avenue has become so unpleasant to walk along. What will happen to that space if it goes dark? 

Whether redevelopment of Times Square through eminent domain was necessary or whether New York could have achieved the same result through quality-of-life policing, broader tax cuts and zoning changes and patience may become a moot point if the first option proves economically impossible. Best to heed the history Sagalyn tells.