Ephemeral New York
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Hidden by billboards for over 100 years, the tiny holdout building in the middle of Macy’s is back in view
The enormous faux shopping bag that served as an advertisement for Macy’s is mostly gone, save for a patch of red facing Sixth Avenue.
Scaffolding covers the ground floor retail space, and dark netting swaths the brick and limestone upper floors.
What’s going on these days at the northwest corner of 34th Street and Sixth Avenue?
For the first time since the early 1900s, the five-story building that prevented Macy’s flagship store from owning the tip of the northwest corner of Herald Square is having its billboards dismantled.
Finally, the little holdout—a lovely if grimy structure, with large studio windows and terra cotta detailing—is once again a visible part of the cityscape.
This building might be the most famous holdout in Manhattan, and it serves as an illustrious reminder of Gotham’s bitter retail wars at the turn of the 20th century.
Macy’s new store and the corner plot, early 1900s
The story begins around 1901. At the time, Macy’s made plans to move its New York City stores from the crowded Ladies Mile shopping district along 14th Street between Fifth and Sixth Avenues to the more spacious and transportation-friendly Herald Square.
They planned to build the new store at 34th Street and Sixth Avenue. Macy’s bought out many smaller businesses that already existed on the site—including a restaurant, a barber shop, and the bawdy Koster & Bial Concert Saloon, where the first projected motion pictures made their debut.
The holdout building in 1906
The only lot they couldn’t get was a 30 by 50 foot corner remnant of an old farm that held an existing structure. “This tiny parcel was the property of an old-time New Yorker, Rev. Duane Pell,” wrote Edward Hungerford in his 1922 book about Macy’s, The Romance of a Great Store.
“It was given to understand that \[Pell’s\] asking price for the small corner was $250,000, an astonishing figure for such a tiny bit of land . . . but Dr. Pell felt that he had held the key to the entire important Herald Square corner and that he was justified in asking any price he saw fit.”
Despite the high price, Macy’s ultimately agreed to buy the plot from Pell, as they felt it was crucial to own the corner.
The holdout building covered in ads, 1907
Yet before Macy’s could sign the deal, Pell sold the plot for $375,000 to an agent for Henry Siegel, the owner of rival department store Siegel-Cooper, according to New York’s Architectural Holdouts, by Andrew Alpern and Seymour Durst.
Known as “The Big Store,” Siegel-Cooper was a massive emporium with 120 departments and 3,000 employees on Sixth Avenue and 18th Street.
Macy’s billboards in 1964
Opened in 1896, Siegel-Cooper occupied a section of Sixth Avenue near other legendary department stores of the era, like B. Altman’s and Hugh O’Neill’s.
Once the plot was transferred to his name, Siegel cannily offered it to Macy’s in exchange for one of their 14th Street stores, which Macy’s planned to leave vacant after the move to Herald Square.
2026 image from the New York Post
Macy’s emphatically turned Siegel down. Instead, they built the Herald Square store around the holdout corner, a spiteful move that suggested Macy’s power and dominance.
“In 1903 Siegel-Cooper, defeated after Macy’s had opened the year before, demolished the small structure that occupied the corner and constructed a five-story building, designed by William Hume,” states Urban Archive.
At some point in the early 1900s, Siegel lost ownership of the five-story building. Since the 1920s, Macy’s has leased billboard space on the facade and plastered it with Macy’s ads, including the ad for the red and white shopping bag.
So what prompted the holdout building to emerge out of the shadows now?
Apparently the owner of the building for more than 60 years, Kaufman Realty, planned to lease the facade space to another company. A New York Post story from 2021 describes the company as a “prominent online retailer.”
When, or if, the new billboards make their appearance on this 34th Street corner isn’t known. Get a closeup view of this long-hidden holdout while you can—an emblem of how powerful corporations are willing to fight for precious real estate in Midtown Manhattan.
\Third image: unknown; fourth image: [MCNY, X2010.7.1.1948; fifth image: Wikipedia; sixth image: MCNY, F2011.33.428; seventh image: Jimin Kim/SOPA Images/Shutterstock via New York Post\]
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Tags: History of Macy's on 34th Street Herald Square, Holdout Building on 34th Street Macy's, Holdout buildings Herald Square, Holdout Buildings in New York City, Macy's holdout building, Macy's shopping bag ad on neighbor building, Siegel-Cooper The Big Store NYC
This entry was posted on July 27, 2026 at 12:50 am and is filed under Defunct department stores, Midtown, Random signage. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.
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