Walk down Fifth Avenue between 52nd and 53rd Street and you can't miss it. Or, well, you can't miss what it used to be. For decades, the aluminum-clad skyscraper at 666 Fifth Avenue stood as a shimmering, slightly ominous monument to mid-century corporate ambition. It had that embossed "666" glowing in red neon high above the Manhattan skyline, a detail that launched a thousand conspiracy theories and more than a few jokes about the devil’s real estate portfolio.
But the real story isn't about numerology. It’s about money. Specifically, a lot of money—and one of the most aggressive, perhaps even reckless, real estate gambles in the history of New York City.
When the Kushner Companies, led by a then-26-year-old Jared Kushner, bought the 666 Fifth Avenue building in 2007, they didn't just buy an office tower. They bought a massive headache. The price tag was $1.8 billion. At the time, that was the highest price ever paid for a single office building in the United States. They put down about $50$ million in equity and borrowed the rest. It was a play based on the assumption that rents would keep skyrocketing forever. Then 2008 happened. The global financial crisis didn't just move the goalposts; it set the whole stadium on fire.
The Debt Trap and the Quest for a Savior
The math never really worked. To break even on a $1.8 billion acquisition with that much leverage, you need tenants paying top-tier, record-breaking rents. But 666 Fifth Avenue wasn't exactly the shiny new toy on the block anymore. Built in 1957 by Tishman Realty and Construction, the building featured 1.5 million square feet of space but had relatively low ceilings by modern standards. It felt a bit cramped compared to the glass-and-steel giants rising in Hudson Yards or the newly renovated towers on Park Avenue.
By 2011, the building was struggling. The Kushners had to sell off the retail podium—the highly valuable storefronts—to Vornado Realty Trust and others just to keep the lights on and the debt serviced. Honestly, for about a decade, the building became a symbol of "the deal that went wrong." It was a giant, vertical albatross.
People often forget how desperate the situation got. There were rumors of talks with Anbang Insurance Group from China and even potential Qatari investors. The optics were messy, especially once Jared Kushner moved into the White House as a senior advisor. Every meeting about the building's debt was scrutinized by the press as a potential conflict of interest. It wasn't just a business problem; it was a political lightning rod.
The Pivot to 660 Fifth Avenue
Eventually, something had to give. In 2018, Brookfield Asset Management stepped in with a 99-year ground lease, paying $1.286 billion upfront. This was the lifeline. It allowed the Kushner family to pay off the massive mortgage and walk away with their shirts still on, though arguably with a bruised reputation in the tight-knit world of Manhattan real estate developers.
Brookfield didn't just want the building; they wanted to erase its past. They spent upwards of $400 million on a total "reimagining" of the space. The first thing to go? That infamous address. The building was officially rebranded as 660 Fifth Avenue.
They stripped the old embossed aluminum panels—the "skin" of the building—and replaced them with floor-to-ceiling glass. It’s a complete transformation. If you look at it today, the aesthetic is entirely different. It went from a heavy, 1950s metal block to a light, transparent, modern office hub. The red neon 666 is gone. In its place is a sleek, minimalist facade designed by the architecture firm Kohn Pedersen Fox (KPF).
Why the Location Still Commands a Premium
You might wonder why anyone would bother spending half a billion dollars to renovate an old tower instead of just tearing it down. In Manhattan, it's all about the bones. And the dirt. 660 Fifth Avenue sits in the heart of the Plaza District. You have MoMA right there. You're a few blocks from Central Park. You're surrounded by the flagship stores of some of the world's wealthiest brands.
The building also has massive floor plates. In a city where many older buildings are skinny and inefficient, 660 Fifth Avenue offers large, open spaces that modern tech and finance firms crave.
- Natural Light: The new glass curtain wall isn't just for looks; it allows light to penetrate deep into the floor, a massive upgrade from the original small windows.
- Infrastructure: Brookfield gutted the elevators, the HVAC systems, and the lobby. It’s basically a new building inside an old frame.
- Outdoor Space: They added several landscaped terraces, which became a "must-have" feature for office tenants following the COVID-19 pandemic.
It's a weird irony. The building that almost bankrupted its owners because of a bad bet on the market has become one of the most successful examples of "adaptive reuse" in Midtown. Companies like Macquarie Group and the law firm Cadwalader, Wickersham & Taft have signed major leases there recently. They aren't moving into a cursed building; they’re moving into a Class-A masterpiece.
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Lessons from the 666 Fifth Avenue Saga
What can we actually learn from this saga? First, that leverage is a double-edged sword. In a rising market, borrowing 95% of the purchase price makes you look like a genius. In a flat or falling market, it makes you a target. The Kushners weren't the only ones who overpaid in 2007, but they were the most visible.
Second, the "666" branding was a legitimate hurdle. While New Yorkers are generally cynical, having your corporate headquarters at an address synonymous with the "number of the beast" isn't exactly great for the vibes. The rebranding to 660 Fifth was a masterstroke of corporate boringness. Boring is good in real estate. Boring is stable.
Third, the office isn't dead—it's just bifurcated. We hear a lot about the "office apocalypse," but what’s really happening is a flight to quality. Lower-tier buildings (Class B and C) are dying. But top-tier buildings with great light, air, and amenities are still commanding high rents. 660 Fifth Avenue managed to jump from the "struggling" category to the "elite" category through sheer force of capital.
What to Look for Next
If you’re tracking the New York real estate market or just interested in the history of the skyline, keep an eye on the retail portion of the building. While the office floors are filling up, the Fifth Avenue retail corridor is still recalibrating. The success of the building's ground-floor tenants will be the final indicator of whether this massive turnaround was truly a success.
You should also look at the "Brookfield Model" for other aging Midtown towers. There are dozens of buildings from the 50s and 60s along Third, Sixth, and Lexington Avenues that are facing the same fate 666 Fifth once did. Expect more "re-skinning" projects as developers realize it’s often cheaper and faster than starting from scratch.
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Actionable Insights for Real Estate Watchers
- Study the "Ground Lease": If you're into the mechanics of big deals, look into how Brookfield structured the lease. It’s a fascinating way to control a property without technically owning the dirt forever.
- Monitor Occupancy Trends: Watch the leasing velocity at 660 Fifth compared to the newer towers at Hudson Yards. It tells you if tenants prefer "prestige" locations (Fifth Ave) or "new" neighborhoods.
- Architecture Matters: Take a walk past the building and compare it to the older photos. The shift from aluminum to glass is the best real-world lesson you can get in how facade design impacts a building's perceived value.
The building at 666 Fifth Avenue—now 660 Fifth—is no longer a cautionary tale of debt. It’s a case study in how a billion dollars and a new name can make people forget almost anything. It's not about the devil anymore. It's just about the rent.