You’ve seen it. Even if the name Five Times Square doesn’t immediately ring a bell, if you’ve walked through the neon-soaked intersection of 42nd Street and Seventh Avenue, you’ve stood in its shadow. It’s that massive, sleek tower of glass and steel that anchors the southern end of the most famous crossroads in the world. It’s a building that shouldn't really work, yet it defines the modern corporate aesthetic of Manhattan.
Honestly, it’s kind of a miracle it exists at all given how messy the 42nd Street Development Project was back in the day.
Most people just walk past the retail shops on the ground floor—maybe grabbing a coffee or looking at the digital billboards—without realizing they’re looking at a piece of real estate history. This isn't just another office block. It’s a 1.1 million-square-foot behemoth that basically signaled the end of the "Old Times Square" and the birth of the corporate playground we see now.
The Ernst & Young Legacy and the Big Move
For the longest time, Five Times Square was synonymous with one name: Ernst & Young (EY). They weren't just a tenant; they were the soul of the building for two decades.
In the late 90s, Times Square was still shaking off its grittier reputation. Bringing a "Big Four" accounting firm into the heart of the theater district was a massive gamble by the developers, Boston Properties. It worked. EY signed a lease that was legendary in real estate circles, taking up nearly the entire tower. It was a statement. It said that Times Square wasn't just for tourists and theaters anymore—it was for serious, global business.
But things change. Trends shift.
By 2017, the buzz started. EY was looking at the shiny new Hudson Yards development. They eventually moved their headquarters there, leaving a massive hole at Five Times Square. You might think a million square feet of vacant space in the middle of Manhattan would be a disaster. Kinda. But it actually paved the way for a massive $150 million renovation that is currently turning the building into something much more modern.
Why the Architecture Actually Matters
The building was designed by Kohn Pedersen Fox (KPF), a firm that basically specializes in making glass look cool. They didn't just build a box. The tower has this distinct, sloping facade that mimics the chaos and energy of the street below.
💡 You might also like: Zimbabwean Dollars to USD Explained: What Most People Get Wrong
- The structure stands 37 stories tall.
- It utilizes a complex "curtain wall" system.
- The tower is actually built over a subway station, which made construction a literal nightmare for the engineers.
KPF had to deal with the strict "zoning" requirements of Times Square. In this part of the city, you have to have bright lights. You have to have signage. The building was designed to integrate these massive LED displays into its very skin. It’s one of the few places where the architecture is legally required to be loud.
The Billion-Dollar Handshake
Let's talk money, because Five Times Square is a goldmine. In 2014, the building sold for a staggering $1.5 billion. Think about that number. That’s more than the GDP of some small countries.
The buyer was David Werner, a legendary (and somewhat private) figure in the New York real estate world. He partnered with RXR Realty and other investors to pull off the deal. It remains one of the largest single-asset real estate transactions in the history of New York City.
People often ask why a building would cost that much.
Location? Obviously.
But it’s also about the "credit-worthiness" of the tenants. When you have a massive firm paying rent for 20 years, the building becomes a "bond with a roof." It’s a safe place for billionaires to park their cash.
The Post-Pandemic Pivot
The world looks different now. Remote work is real. Office towers are struggling. So, what happens to Five Times Square?
RXR Realty isn't just sitting around. They are currently overhauling the place to appeal to the "next generation" of workers. We’re talking about "amenity centers" that look more like luxury hotels than offices. There’s a new lobby, a fitness center, and even a rooftop terrace which, frankly, offers some of the best views of the New Year's Eve ball drop without having to stand in a pen for 12 hours.
The ground floor retail is also a major player. Disney had a massive presence here for a long time. These storefronts are some of the most expensive per square foot on the planet. Why? Because millions of people walk past them every month. It’s not just a shop; it’s a billboard that sells products.
Common Misconceptions About the Tower
People often confuse Five Times Square with its neighbors. It is not the building where the ball drops (that’s One Times Square). It’s also not the New York Times building (that’s on 8th Avenue).
Another mistake people make is thinking it's an "old" building. Compared to the Art Deco skyscrapers nearby, Five Times Square is a baby. It was completed in 2002. It represents the "millennial" phase of NYC architecture—lots of glass, very efficient, and designed specifically for computer-heavy workspaces.
The "Subway" Secret
One of the coolest things about the building is what’s underneath it. Because it sits right on top of the Times Square–42nd Street station, the developers had to integrate the subway entrance into the building's footprint.
If you go into the basement levels, you are essentially inside the busiest transit hub in North America. The engineering required to keep a 37-story tower from vibrating every time the Q train rolls through is nothing short of insane. They used specialized dampening materials and heavy-duty foundations that go deep into the Manhattan schist (the super-hard bedrock that allows these towers to stand).
What’s Next for This Landmark?
As we head deeper into 2026, the focus for Five Times Square is all about "ESG" (Environmental, Social, and Governance) standards. Modern companies won't rent space in "dirty" buildings anymore. They want LEED certification. They want energy efficiency.
The current owners are pouring millions into making the building "greener." This includes:
- Upgrading the HVAC systems to be more efficient.
- Installing "smart" glass that reduces heat gain.
- Redesigning the interior to maximize natural light (which supposedly makes workers 15% more productive, according to some studies, though I suspect it just makes them less grumpy).
The loss of EY was a blow, but the repositioning of the building seems to be working. New tenants are signing on, drawn by the fact that you can’t get more "New York" than an office overlooking the red steps.
📖 Related: 60 Hong Kong Dollars to US: Why the Math Might Surprise You
Actionable Insights for Your Next Visit
If you’re a tourist, a local, or a business professional looking at the building, here’s how to actually "use" Five Times Square:
- Don't just look up. The retail level often features flagship stores that have exclusive merchandise you won't find in your local mall. It’s worth a quick walkthrough for the "spectacle" factor alone.
- Use the "Secret" Entrance. The subway entrance built into the building is often slightly less crowded than the main entrances on the corners. It’s a pro tip for avoiding the worst of the tourist crush.
- Appreciate the Lighting. If you’re there at night, look at how the digital signs are integrated into the glass. It’s a masterclass in how to do "commercial" architecture without it looking like a giant neon mess.
- Business Intelligence. If you’re in real estate, keep an eye on the leasing activity here. Five Times Square is the "canary in the coal mine" for the Midtown office market. If this building stays full, the city is doing just fine.
The tower stands as a monument to the era when Times Square went corporate. It might not have the history of the Empire State Building, but it has the heartbeat of the modern city. It’s expensive, it’s loud, and it’s unapologetically Manhattan.