Photo: Illustrations by Mark Nerys/New York Magazine

It’s been nearly 50 years since New York enacted the law that protects its landmarks, and the Museum of the City of New York’s “Saving Place” exhibition looks back on that record of rescue. The most self-evident work has been done: Old, precious buildings soldier on under legal protection, and all five boroughs are daubed with historic districts where construction is severely restricted. Decisions by the Landmarks Preservation Commission are regularly met with outrage, but New York is no longer divided into preservationists and everyone else.

Yet even as the celebrations get going, the American Folk Art Museum sits on death row. New debates, over quirky youngish buildings tailored for highly specific use, are trickier than the old. This city is full of adaptable architecture—sugar factories that become condos, sweatshops turned into tech-start-up offices, synagogues made into theaters. Still, Elizabeth Diller, one of the designers of MoMA’s next incarnation, has referred to the Folk Art building as “bespoke” architecture, meaning that the architects Tod Williams and Billie Tsien fitted it so artfully to their client’s needs that it won’t meet anyone else’s.

Time isn’t always kind to innovative design. When occupants move on or functions fade, refined, idiosyncratic buildings become vulnerable. With no consensus about their architectural importance, they can be hard to defend; cumulatively, they provide an antidote to the march of generic efficiency. Consider these six buildings, some of which have been at the center of recent landmarking fights, ­others of which may be in the future. What would you try to save, and why?

Top Photo: U.N. Secretariat Building, by Oscar Niemeyer, Le Corbusier, and Wallace Harrison:

Saved By Its Own Idealism
The derelict symbol of global diplomacy needed new everything.
The United Nations may be an icon, but since it’s not technically in the city, or even in the U.S., it can’t be landmarked. And the obvious way to deal with the narrow, cramped, beat-up Secretariat Building (and its low-rise neighbors) was to tear it down. The U.N.’s Vatican-like aversion to change—plus a desire to avoid the international arguments that a new structure would foment—may be what saved it, leading to a $2.1 billion renovation that involved entirely new glass-curtain walls. The Conference Center and General Assembly Building are being restored with similar reverence.
Status: Under Meticulous Renovation

O’Toole Building, by Albert Ledner:
The Accidental Survivor
A Village symbol was sacrificed to a developer but redeemed by bankruptcy.
Built in 1964 for the National Maritime Union, the “Overbite Building” later became the heart of St. Vincent’s Hospital and an icon of the struggle against AIDS. In 2008, the broke hospital’s administrators decided that the building had to go to make way for a larger complex. St. Vincent’s went under before the deal could be consummated, leaving the O’Toole Building in preservation purgatory. Now it’s being reborn as an emergency medical center, its architectural identity crisply restored. Chalk this one up to luck. 
Status: Saved and Restored

2 Columbus Circle, by Edward Durell Stone:
Hated Too Quickly, Loved Too Late
Its defenders defeated, the late-modern oddball was stripped and reskinned.
When Huntington Hartford’s Gallery of Modern Art opened in 1964, the Times’ Ada Louise Huxtable memorably ridiculed it as a “die-cut Venetian palazzo on lollipops.” Her successor Herbert Muschamp later pinpointed its pre-Stonewall gay life (“The bar poured the swingin’est Singapore sling in town,” he wrote). The gallery closed after just five years, and the building grew seedy. By the 1990s, despite growing support, the Landmarks Preservation Commission refused to even discuss protecting it. In 2005, the Museum of Arts and Design plowed through opposition and gave it a gut renovation and a new façade.
Status: Heavily Altered

Fifth Avenue Apple Store, by Bohlin Cywinski Jackson:
The Building As Brand
Ultimate minimalism, but would another business ever want an Apple hand-me-down?
The glass cube that opened in 2006 accomplishes a staggering number of architectural tasks. It places a giant Apple logo in a display case, evokes the beloved Power Mac G4, translates a corporate design aesthetic to huge scale, and redeems the GM Building’s grim sunken plaza. In 2011, the pioneering assemblage of 90 sheets of glass was replaced by an even more transparent structure of only 15 pieces. But those qualities are exactly the ones that might make a future tenant balk—especially since one of those immense panes reportedly cost $450,000 to replace when a snowblower shattered it in January. 
Status: Unthreatened (For Now)

IAC Building, by Frank Gehry:
One Man’s Fantasy
A media mogul’s seat of power may be difficult to sell.
The billowing white-glass schooner anchored at the western edge of Chelsea was commissioned by IAC chief Barry Diller, who has a thing for boats. In an orthogonal city, it dares to wobble and wave. Sure, the interior spaces can be arrestingly odd, but the building carries a message about the company’s defiance of conventional wisdom. However, if IAC’s empire should crumble, Diller retire, or tech get square, who will cherish Gehry’s folly? Glass-curtain walls get old, and future owners may flinch at the appalling expense of replacing all those custom-curved, fritted panes. 
Status: Safe Today, But Who Knows?

Queens Public Library, by Steven Holl:
A Built-in Identity Crisis
With the public library’s function in flux, a new building could be obsolete even before it’s finished.
Holl’s effusive branch library at Hunters Point isn’t even built yet, and already it seems ­brilliant—and possibly doomed by a wayward budget. The original design with its seemingly hand-carved openings is as much flexible public space as it is book repository. The process for public building being a tortured one, the architecture could go all stolid by the time it’s built, and the conventional wisdom on book spaces is likely to have changed by then, too. Like Eero Saarinen’s TWA terminal at JFK, it could end up as a charmer that doesn’t fit future needs.
Status: Still Unbuilt; ­Potentially Compromised

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