It was a record. A massive, staggering, $1.8 billion record. In 2007, when the Kushner Companies decided to buy 666 5th Ave Kushner was just a name associated with a rising real estate scion, Jared, who wanted to make a splash in the big pond of New York City. They didn't just make a splash. They jumped into the deep end with a lead weight tied to their ankles.
At the time, the purchase price for the 41-story aluminum-clad tower was the highest ever paid for a single office building in the United States. It was the peak of the market. Everyone was drunk on cheap credit and the belief that Manhattan real estate only went up. But then the world broke. The 2008 financial crisis hit, and suddenly, that $1.2 billion in debt sitting on the property looked less like a bold investment and more like a ticking time bomb.
Honestly, the building became a bit of a ghost. Not literally, though the address—666—certainly invited plenty of "omen" jokes from the press. It was a ghost in the financial sense. It wasn't making enough money to cover its bills. For a decade, the saga of this midtown skyscraper was a masterclass in high-stakes survival, international diplomacy, and the kind of "too big to fail" maneuvering that makes the average person's head spin.
Why 666 5th Ave Was Such a Massive Gamble
You have to understand the math, or rather, the lack of it. When Jared Kushner orchestrated the deal, the building’s net income was roughly $50 million. The annual debt payments? About $100 million.
You don't need a Harvard MBA to see the problem there. The plan was basically a "value-add" play. The idea was to hike rents, renovate, and maybe turn the whole thing into a mix of ultra-luxury condos and high-end retail. But the timing was brutal. By 2011, the Kushners had to sell a 49.5% stake in the office portion to Vornado Realty Trust just to keep the lights on and the lenders at bay.
Vornado, led by the legendary Steven Roth, isn't known for doing favors. They are sharks. For years, Roth and Kushner were locked in a stalemate. Jared wanted to build a massive, Zaha Hadid-designed skyscraper that would have required tearing the whole thing down and spending billions more. Roth? He wanted to just keep it as an office building and wait for the market to turn. It was a deadlock. Two different visions, one crumbling balance sheet.
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The Search for Global Capital
By 2016, things got weird. Jared Kushner was now a key figure in Donald Trump’s presidential campaign. Suddenly, a struggling office building on 5th Avenue wasn't just a real estate problem; it was a potential national security concern.
There were talks with Anbang Insurance Group, a massive Chinese conglomerate. That deal fell apart under intense public scrutiny. Then there were reports of meetings with Qatari investors. Critics were screaming about conflicts of interest. Imagine being a foreign government—if you "save" the building owned by the President's son-in-law, what do you get in return?
The Kushners eventually bought out the remaining years of Jared's interest to distance him from the business, but the shadow of 666 5th Ave Kushner followed him into the White House anyway. It became the ultimate symbol of the intersection between private wealth and public power.
The Brookfield Bailout: A 99-Year Lifeline
In 2018, the saga finally reached its climax. Just as a massive $1.4 billion debt payment was coming due—the kind of payment that usually ends in foreclosure—Brookfield Asset Management stepped in.
They didn't just buy it. They signed a 99-year lease for the office portion and paid the entire 99 years of rent upfront. That’s nearly $1.3 billion. It was a miracle. Or a very calculated bet.
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Brookfield is one of the biggest players in the world. They saw something others didn't. They immediately set to work rebranding the building to 660 Fifth Avenue. Gone was the 666. Gone was the dated aluminum "skin" of the building. They spent hundreds of millions replacing the facade with massive, floor-to-ceiling glass windows.
Why the Rebrand Matters
- The Address Problem: Let’s be real, 666 is a tough sell for certain tenants. Moving to 660 Fifth Avenue was a psychological clean slate.
- The Light: The old building had these tiny windows. In modern office culture, if people don't get natural light, they quit. Brookfield changed the entire aesthetic.
- Retail Value: The retail at the base of the building, which includes Uniqlo, is actually incredibly valuable. It’s one of the busiest corners in the world.
The Reality of Commercial Real Estate Today
The story of this building is actually a microcosm of what’s happening in New York right now. Older, "Class B" office buildings are dying. If you have a building from the 1950s with low ceilings and bad HVAC, you're in trouble.
Brookfield’s gamble was that by spending enough money, they could turn an old dog into a new trick. They bet that top-tier companies would still pay premium prices for "Class A" space in the best location in the city. And for the most part, it's working. They've signed major tenants like Macquarie Group and some high-end law firms.
But for the Kushners, the exit was more about survival than a victory lap. They walked away with enough cash to pay off the lenders, but the astronomical profits they imagined back in 2007 never materialized. It was a decade of stress for a break-even result.
Actionable Lessons from the 666 5th Ave Saga
If you’re looking at this story and wondering what it means for the "regular" investor or just curious about how the big boys play the game, here are a few things to take away.
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Never bet on a perfect market. The Kushners bought at the absolute top with no margin for error. If your investment requires everything to go perfectly just to break even, it’s not an investment; it’s a prayer.
Debt is a double-edged sword. Leverage makes you rich when things go up, but it destroys you when they stall. The 2018 deadline could have ended the Kushner real estate empire if Brookfield hadn't seen a path to profit.
Rebranding is more than a name change. You can't just change the number on the door. Brookfield understood that to fix the "Kushner building," they had to physically transform it. They stripped it to its bones.
Watch the "Flight to Quality." In 2026, we're seeing a massive divide in real estate. The best buildings are doing great. The average buildings are being converted into apartments or sitting empty. If you're looking at property, the "middle" is the most dangerous place to be.
To really understand what happened, you should look into the specific zoning changes that allowed the renovation. It shows how much the city government influences these billion-dollar deals. You can also research Brookfield’s current portfolio—they are essentially the "fixers" of Manhattan's distressed assets. Tracking their next move usually tells you where the smart money is heading before the rest of the market catches on.