As we explored two weeks ago, the battle for Times Square was long and messy. On February 24, 1998, the Giuliani administration won a major legal battle when the New York Court of Appeals ruled that the City had legally re-zoned Times Square, a seeming death knell for the local adult entertainment industry.

One of the initiatives Rudy Giuliani is most known for is turning Times Square, a neighborhood that was awash in porn shops, strip clubs, and thinly disguised brothels, into a Disneyfied tourist destination. In 1995, the New York City Council amended the City’s Zoning Resolution, banning “adult” entertainment and businesses in certain commercial districts.

Even though Times Square had been known as a seedy part of the town since the 1930s, the number of adult establishments in New York City had grown from nine in 1965 to 177 in 1993, mostly in Manhattan. (Number may have peaked during the 1970s.) Many studies throughout the 80s and early 90s had proposed  “cleaning up” Times Square. Of course, most of these 177 businesses were operating legally, and when the Zoning Amendment looked certain to put them out of business, they sued.

The legal challenge, Stringfellow’s of New York v. City of New York, was always going to be an uphill battle, but it was far from frivolous. Impressive First Amendment lawyers lined up against the City: the New York Civil Liberties Union (a major Giuliani nemesis), which represented patrons of these establishments; Fahringer & Dubno (led by Herald Price Fahringer, Larry Flynt’s attorney), which represented the establishments; and Mark Alonso, who represented Stringfellow’s, a gentlemen’s club.

Yet this legal firepower couldn’t overcome the strong judicial presumption in favor of municipal re-zoning. Though the Court of Appeals, New York State’s highest court, acknowledged that the Zoning Amendment aimed to curb speech protected by the First Amendment, it gave deference to the City’s zoning powers. The courts may have been swayed by the City’s assurance that the establishments could open in industrial neighborhoods, like Long Island City. Over the years, however, Long Island City and many other neighborhoods were similarly re-zoned.

After two years of litigation, on February 24, 1998, the Court of Appeals ruled in favor of the City. One “Show World” patron lamented, “I’ve been coming here since I was ten. Where we gonna go now?”

Giuliani was triumphant, gloating that now the City could “reduce the number [of adult establishments] in the city to something like 20 or 30.” Given that his lawyers had argued precisely the opposite, this bravado nearly proved costly. The plaintiffs re-filed in federal court, but the District Court and Circuit Court were unwilling to re-litigate the case.

The story didn’t end there. The next question was how to define “adult establishments,” a murky term that led to topless bars adding everything from sushi to Shakespeare, porn shops adding action movies and adult theaters adding Bollywood in an effort to stay legal.  This sidestep obviously infuriated Giuliani, and right after 9/11, the City Council amended the law yet again. The constitutionality of the new, even more restrictive law, is still winding through the court system.

In the end the adult entertainment industry was most ravaged not by Rudy Giuliani, but the internet. Demand for erotic theater and videos took a huge hit, and many of those businesses shut down. Those that remained faced down the greatest foe to small business, rising commercial rents.

A 2009 report by blogger EV Grieve tracked down 11 strip clubs/peep shops/DVD stores in the Times Square/Port Authority area, and in 2010 there was a report of a hidden porn theater, like those last elusive checker taxis. When the last adult stores and venues are gone, the culprits will be the internet, the rent being too damn high, and the cultural tastes of midwestern tourists, not a legal brief or Rudy in a china shop, and despite the power of the First Amendment. Just another example of humans being tossed around by the riptides of history.

Read more from Today in NYC History on Untapped Cities. If you’re curious about more of the legal issues in this case, or just want to learn more about New York City political history, check out Janos.nyc.