This is the latest in a series of (edited, condensed) walks around the city. Jerold S. Kayden teaches law and urban planning at the Harvard Graduate School of Design, where he holds a chair named after the lawyer who greatly influenced the drafting of New York’s (and America’s) first comprehensive zoning legislation. Mr. Kayden clerked for Supreme Court Justice William J. Brennan Jr., and is an expert on the city’s so-called Privately Owned Public Spaces. He doesn’t seem to mind being referred to as the Pops of POPS. He mapped a legal-minded itinerary along 42nd Street from Times Square to the East River, taking in the United Nations, Tudor City and Kevin Roche and John Dinkeloo’s recently, lovingly renovated Ford Foundation, all architectural must-sees. For the sake of brevity, we decided beforehand to skip other obvious landmarks like the Chrysler Building, the New York Public Library and the Daily News Building. In the event, we covered a semester’s worth of land-use law by the time we reached Grand Central, which seemed enough for one walk, so we won’t get to any of those East Side favorites in this conversation.

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In the mid-80s, Philip Johnson and his partner John Burgee proposed turning Times Square into a kind of antiseptic office park with four Postmodern office towers and a giant sculpture of an apple by Robert Venturi and Denise Scott Brown. That might have been a bullet dodged but I can’t say that what we ended up with is either very attractive or wholesome.

Speaking of wholesome, an interesting issue that arose was where the adult entertainment businesses would go. The city decided to enact what some of us in the land use field refer to as “erogenous zoning”: prohibiting adult entertainment uses from residential areas, some manufacturing and commercial districts, requiring that they could locate no closer than 500 feet from schools, day care centers, houses of worship. That ordinance was challenged on constitutional grounds, because adult entertainment also has rights under the First Amendment free speech clause. On another, related note, you remember the controversy over the Elmos and desnudas in Times Square?

In 2015, Mayor Bill de Blasio entertained the then-police commissioner Bill Bratton’s idea of ripping out the Bloomberg-era pedestrian plazas — despite their popularity and the fact that they boosted business and lowered the number of traffic accidents — because they had attracted some unruly costumed panhandlers and topless women wearing body paint. An anti-Semitic Elmo was reportedly ranting outside Toys “R” Us and a Cookie Monster shoved a 2-year-old.

Elmo and Cookie Monster have free speech rights, too, which the city can regulate by declaring where they can operate, within designated zones. Under the Constitution, the government can say, “Here you can speak, there you can’t. You can do it at this hour, but not at that hour, you can speak in a normal voice but not use a bullhorn.” But it has to be reasonable regulation.

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