It’s hard not to love New York’s holdout buildings

A holdout building is a piece of property that refused the wrecking ball. Instead of bowing to threats of eminent domain or accepting an offer to sell, the building’s owner holds their ground and forces developers to change plans.

In New York City, that doesn’t seem to usually stop developers; they simply build around the holdout. and that leads to some pretty incongruous streetscapes, like this one above. Here, a late 19th century tenement continually gets the squeeze from two postwar towers on East 79th Street between First and York Avenues.

Some holdout buildings stood their ground decades ago. This yellow brick walkup was probably part of a long line of once-fashionable townhouses on East 20th Street near Fifth Avenue in the mid- to late 1800s. Tall loft buildings replaced them in the early 1900s…but the set-back holdout at number 34 remains.

Was this holdout in the Diamond District on West 47th Street once bright white and glorious? That balcony makes it look like a palace flanked by two dour bullies.

This skinny holdout (only wide enough for one window per floor!) was built in 1865, when West 46th Street was near the magnificent Croton Reservoir at 42nd and Fifth. I imagine this was another block of residences slowly replaced by tall loft buildings after the turn of the century…except for this one.

Nat Sherman Cigars operated out of this townhouse for years before closing up shop in 2020, a casualty of the pandemic. Though the townhouse itself wasn’t built until 1971 at 12 East 42nd Street, a previous holdout building stood its ground between these bigger guys, reserving the space.

This last one is a holdout mystery. The photo was sent to me years ago, and I’ve had no luck tracking down where exactly it was taken. In any event, it’s hard not to love the little cabin and the walkup behind it (those shutters!), both almost swallowed up by the cityscape around it.

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