WHEN Pennsylvania Station met its sorry end 42 years ago last fall, Ralph Stephenson, a counterman at the station's Savarin restaurant, was asked about the fate of the majestic granite-clad structure. "This city's got the right name -- New York," he remarked. "Nothing ever gets old around here."

New York has long reigned as the citadel of creative destruction. Spires thrust ever higher, the old sloughed off to make way for the new. To New Yorkers at the dawn of the modern preservation movement, however, the sacking of Penn Station was a rude awakening. Demolition would forever be an unsavory affair, the wrecker a wanton agent of destruction.

Yet contrary to demolition's enduring status as an architectural crime, the unbuilding of New York has shaped our city as powerfully and poignantly as the storied skyline's construction. Though largely relegated to history's footnotes, demolition contractors, with caroming cast-iron wrecking balls and ledge-dangling bravura, have left a mark on the city in the form of conspicuous absences. In the heady optimism of the early 20th century, demolition was an evocative, even enthralling part of the urban scene. Sidewalk superintendents were agog at the daredevilry on display. Far from today's well-regulated wrecking world, which is safer but hardly as entertaining, the city under siege could be a vista of sublime, lyrical beauty, and the lowly wrecker a workaday hero in our midst.

In the heyday of heroic Gotham demolition, no wrecker loomed larger than Jacob Volk. The son of a Delancey Street butcher, Mr. Volk "pulled down the best places, and was proud of it," according to a profile in The New Yorker, which went on to add, "He never passed a tall building without an appraising glance and a sigh." His Park Avenue offices were stylishly appointed, and upon his death, in 1929, the essayist E. B. White described him as "the greatest wrecker of all time."

In 1910, Mr. Volk vanquished the 22-story Gillender Building in Lower Manhattan, loosing 250 men upon the tallest building that had ever been razed. The flabbergasted press called it "the first time that such a high-class office building, representing the best type of modern fireproof construction, has been torn down to make way for a still more elaborate structure." (The Gillender was only 12 years old.) Enter Mr. Volk, who strode over busted balustrades like an admiral on his bridge, barking through a megaphone at his crew. Swarms of masons and mechanics crushed cornices and stripped away stone while Mr. Volk used pneumatic guns to blast brickwork. "If it cannot be managed with the air guns," he declared, "we shall use dynamite." When the building had been stripped to its steel frame, power-winches lowered beams to idling trucks. Just 45 days later, no trace of the Gillender remained.

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Though caricatured as cloddish brutes, wreckers of Mr. Volk's day were exceptionally skilled tradesmen. They would whittle away a structure to gather salvageable spoils of the trade. Demolition was construction in reverse: fixtures and appliances were sold; wood studs and flooring pried up, studiously denailed, and tied in bundles for reuse; and bricks cleaned by fiendish characters who could knock the mortar off 5,000 bricks a day. Laborious, yes. Wasteful, no. It was an elegant way to wreck.

By the 1930's, builders had no time for such niceties. When the old Hotel Majestic at Central Park West and 72nd Street was sundered, wreckers smashed marble bathroom fixtures with sledgehammers and punched out windowpanes with poles. To recut the rosewood, mahogany and black walnut used in the hotel's old Glow Room and Rose Room was simply too expensive, according to the developer Irwin S. Chanin, who built an apartment house on the site. "It is going out of the Majestic as badly splintered firewood," he told The New York Times in 1929.

The quest for destructive speed soon yielded that world-jarring tool of the trade: the wrecking ball. The restaurateur Toots Shor used it to brilliant effect when his establishment at 51 West 51st Street was demolished in 1959. Toots Shor's "was almost surely the most widely known saloon on earth," the columnist Red Smith later recalled, so it was a moment for the history books when the structure made way for a planned 48-story hotel. On the fateful morning, Shor got behind the controls of a crane and swung the one-and-a-half-ton iron wrecking ball -- painted to look like a baseball, in honor of his sports-bar milieu -- and then cheekily posed with his handiwork.

Colorful characters like Toots abounded in the wrecking world, none perhaps more flamboyant than Morris Lipsett, the onetime junk dealer whose company took down Pennsylvania Station. Mr. Lipsett's prowess with an adding machine and a wrecking ball turned him into one of the nation's biggest wreckers. In business with his brother Julius, Morris got his first big break tearing down an aging hotel near Chautauqua, N.Y., hard by Lake Erie. Hope of profits evaporated after their ruinous attempt to take down the structure. (When Mrs. Lipsett suggested that her husband might consider a different line of work, Morris replied philosophically, "You should always look for money where you lost it.")

MANY successes followed, and the brothers' bid to take down the Third Avenue el in 1955 made them veritable civic saviors. A throng of 25,000 turned out to say farewell to the 77-year-old line as city officials led a raucous street pageant from Chinatown to Harlem, passing celebrating citizens along the way: Greeks at 77th Street, Hungarians at 79th, Irish at 84th, Germans at 86th, Puerto Ricans at 106th and Italians at 116th, where Mayor Robert F. Wagner was served pizza and Chianti.

As the Lipsetts knew well, demolition could offer urban revelation. In 1967, when wreckers razed the 47-story Singer Building in Manhattan, at Broadway and Liberty Street, passers-by gazed in wonder at the structure, which many hadn't noticed until it came under attack. Among its heralded Beaux-Arts splendors were silver-gray marble slabs and a cacophony of consoles and cartouches. Such opulence called to mind the 18th-century Italian engraver Giovanni Battista Piranesi, whose etchings of Roman ruins had long been a touchstone for sublime destruction. "Piranesi, anyone?" Ada Louise Huxtable asked as the Singer's domed vaults devolved into rubble. "The master never produced a more impressive ruin than the Singer Building under demolition." Those curious enough to risk being beaned on the head by a chunk of Pavonazzo marble, she said, "will find a scene of rich, surrealist desolation."

Such Piranesian splendors have in turn become history.

Just as the destruction of precious urban artifacts is no longer affably tolerated by many New Yorkers, the lovable, lowly wrecker has changed too. He (and now, increasingly, she) must master hazardous materials management, soil decontamination and mold remediation. Armed with exotic hunks of heavy machinery, these "industrial hygienists" rove through a landscape of sundry perils that have made wrecking sites subject to a battery of federal regulations. Especially in a post-Sept.-11 world, wrecking in New York may never again be as intoxicating as it was in Jake Volk's days.

By the time the Lipsetts began blasting at Penn Station, even they seemed to sense that wrecking times were changing. Nonstop ruin had left them feeling empty. "Just tearing things down didn't make Morris Lipsett happy," The New York Times reported in 1955, noting that the famed destroyer had gone into the construction business "as a sort of balance." Morris had been laying a transmission line across South Dakota and toiling on a new subway in Philadelphia. "Makes a man feel better," he explained.

CITY LORE Jeff Byles is the author of "Rubble: Unearthing the History of Demolition," published in November by Harmony Books.

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