Inside the Woolworth Building: The Cathedral of Commerce That Changed New York Forever

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In 1913, a man who had built his fortune selling five-cent trinkets stood in a brand-new skyscraper in downtown Manhattan and wrote a check for $13.5 million — in cash. No mortgage. No loan. Just a personal check, handed over for the tallest building on earth. Frank Winfield Woolworth had arrived. And New York would never look the same.

For a decade after it opened, the Woolworth Building owned the sky. At 792 feet, it soared above everything else in the city — a neo-Gothic tower of terracotta and glass rising from Broadway like a medieval cathedral reimagined for the modern age. President Woodrow Wilson pressed a button in Washington D.C. to switch on eighty thousand light bulbs at the opening ceremony. The crowd gasped. New York had a new icon.

The Man Who Paid Cash for a Skyscraper

F.W. Woolworth did not come from money. He grew up on a farm in upstate New York and failed his first attempt at retail so badly that his employer refused to pay him. He was twenty-one years old and broke. What he discovered, through years of trial and error, was a radical idea: sell everything for five cents or ten cents, stack the shelves high, and trust that ordinary people would spend if the price was right. By 1909, Woolworth’s five-and-dime empire stretched across hundreds of stores. He was one of the wealthiest men in America.

He hired architect Cass Gilbert to design his monument. Gilbert’s brief was simple: make it the tallest building in the world, and make it beautiful. Gilbert delivered both. He drew his inspiration not from American commercial architecture but from the great Gothic cathedrals of Europe — flying buttresses, gargoyles, pointed arches, and soaring vertical lines. When the building was consecrated by a visiting clergyman who called it “a cathedral of commerce,” Woolworth was delighted. He used the phrase for the rest of his life.

Hidden Rooms and a Private Subway Stop

The Woolworth Building’s most spectacular secrets are not visible from the street. Deep in the basement, there is a private swimming pool — tiled in marble, perfectly preserved, built entirely for Woolworth’s personal use. He also installed a private railway car in the sub-basement levels, connected to the Interborough Rapid Transit system, so he could travel from his building to Grand Central without ever setting foot on the street. Whether he used it regularly is a matter of debate among architectural historians. That it existed is not.

The lobby, open to the public for decades after the building’s completion, was a masterpiece of excess. The ceiling vaults are covered in Byzantine-style mosaics. The walls are lined with veined marble. At the building’s completion, the lobby ceiling depicted allegorical figures representing commerce, labor, and industry — rendered in gold leaf and colored glass. And in the corner, disguised among the official portraits, Gilbert had sculpted two small caricatures: one of himself, hugging a scale model of the building; one of Woolworth, counting nickels and dimes.

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The Race for the Sky — and the Building That Dethroned Woolworth

For seventeen years, the Woolworth Building stood alone at the top of the world. Then, in 1930, two buildings raced to claim the title of world’s tallest in a contest so dramatic it reads like fiction. The Bank of Manhattan Trust at 40 Wall Street and the Chrysler Building competed in secret, each adding floors to beat the other. The Chrysler’s architect hid a 185-foot stainless steel spire inside the building’s crown, assembling it in secret and raising it through the roof at the last moment to claim the title by just two feet. The Chrysler held the record for eleven months. Then the Empire State Building opened in 1931, and the game changed forever.

Woolworth watched all of this from his tower. He died in 1919, before the great race of the 1930s, but in a curious way his building shaped everything that followed. The Woolworth Building proved that a skyscraper could be art — that height and beauty were not mutually exclusive. Every architect who competed for the sky in those extraordinary years was competing, in some sense, against the shadow Gilbert cast on Broadway.

The Conversion: Luxury Condos in a Cathedral

For much of the twentieth century, the Woolworth Building was an office building like any other — just taller and more beautiful than most. Then, in 2012, the upper thirty floors were sold for conversion into private residences. The “Woolworth Tower Residences” became some of the most coveted addresses in New York, with apartments selling for between $10 million and $79 million. The building that Woolworth paid $13.5 million to construct now houses individual apartments worth more than he paid for the whole thing.

The lower floors remain commercial, and the lobby — or what remains publicly accessible of it — retains its extraordinary mosaics and marble. But the building has been partially closed to casual visitors since the conversion, and many New Yorkers who have walked past it their entire lives have never seen the ceiling vaults or the sculpted portraits of Woolworth counting his nickels. That, in some ways, feels appropriate. The best buildings in New York always save their greatest surprises for those who know to look.

What to Know Before You Visit

The Woolworth Building stands at 233 Broadway, in Lower Manhattan, just a few blocks from City Hall and the old City Hall subway station. The surrounding neighborhood rewards exploration on foot: the Brooklyn Bridge is a short walk to the south, and the streets of Tribeca and the Financial District stretch out in every direction.

Tours of the upper floors and the lobby are available through the building’s management, and they are worth booking in advance. The view from the observation levels, now part of the residential conversion, offers one of the most extraordinary perspectives on Lower Manhattan’s skyline — and a reminder that the race to the sky, which defines this city more than any other, began here, on a winter morning in 1913, when a dime-store millionaire switched on eighty thousand lights and showed New York what it could become.

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Plan Your New York Trip

The Woolworth Building is steps from the Brooklyn Bridge, the 9/11 Memorial, and the best of Lower Manhattan’s historic streets. Give yourself a full morning — the neighborhood rewards slow exploration, and the stories hidden in these blocks could fill a book. Start at the Woolworth Building, walk south to the bridge, and let the city reveal itself as you go.