Macy's Herald Square Iconic Red Bag Sign Removed, Revealing Historic Holdout Building

A Familiar Landmark Departs Herald Square

New York City's Herald Square is undergoing a visual transformation as Macy's has removed its iconic, giant red shopping bag sign from its flagship store. The massive four-story sign, which had been a fixture at the busy intersection of West 34th Street and Broadway for decades, has been taken down as part of a modernization effort by the billboard owner. The removal has not only stirred nostalgia among New Yorkers but also revealed a piece of the building's history previously hidden from view.

Unveiling a Century-Old 'Holdout'

The most striking consequence of the sign's removal is the revelation of a century-old building nestled behind it. This structure, known as a 'holdout', dates back to the early 1900s. Its existence is the result of a real estate rivalry from when Macy's first planned its move to Herald Square. A competing downtown retailer reportedly purchased the small plot to prevent Macy's from acquiring the entire block, forcing the department store to build its flagship around the building. The now-visible structure showcases its original brick architecture, complete with boarded-up windows and a weathered exterior.

Reasons Behind the Removal

Macy's stated that the current sign, while beloved, was outdated and its removal is part of broader updates by the billboard owner, Kaufman Realty, to modernize the space. A Macy's spokesperson commented, 'For generations, the iconic sign at Macy's Herald Square has been a recognizable part of the 34th St. experience and a symbol of our deep roots in New York City. As the neighborhood continues to evolve, the current sign – while beloved – is outdated and is being removed as part of broader updates by the billboard owner to modernize the space.'

The situation is understood to stem from a real estate impasse. According to reports, the owner of the holdout building and the billboard owner failed to reach a new agreement regarding the advertising space. Dan Biederman, president of the 34th Street Partnership, explained, 'One firm owns the building and the other wants to keep an advertising sign up on it. They have to make an agreement, and evidently, that didn’t happen.'

A Look Back and Forward

While the exact year the red shopping bag sign first appeared is not definitively stated by Macy's, archival Getty images suggest an early iteration was present by 1994, with some form of large signage occupying the spot since the 1950s. The sign's removal has led to public reactions ranging from sadness and nostalgia to curiosity about what will replace it. Social media users have expressed a desire to see the historic holdout building restored to its original beauty, while others debate the embrace of modern LED signs.

Macy's has indicated that new branding for its Herald Square flagship is forthcoming. 'Soon, Macy's will announce refreshed and dynamic branding for Macy's Herald Square that honors our heritage while reflecting the future of our flagship,' a spokesperson shared. Permits have been issued for the installation of two new LED signs, signaling a move towards modernization, though the specific advertisements remain unannounced. The department store ranked No. 8 on National Jeweler’s 2025 “$100 Million Supersellers” list, with an estimated $1.27 billion in jewelry and watch sales, underscoring its significant retail presence.