The ups and downs of Ashkenazy’s $10 billion portfolio
Since getting into real estate investing as a teenager, Ashkenazy has assembled a portfolio worth an estimated $10 billion. It hasn’t always been smooth sailing, however, especially in the wake of the Covid 19 pandemic that cost him several prime properties and a hefty slug of his personal wealth.
15 million square feet
His portfolio includes 15 million square feet in prime commercial buildings, including The Plaza.
$10 billion
Ashkenazy acquired the long-term lease for this popular tourist attraction in 2011 from mall operator General Growth Properties for a reported $136 million. In 2020 officials with the city of Boston, which owns the land, sent a notice of default after Ashkenazy’s firm failed to pay $2 million in payments. In January 2024 Ashkenazy sold the marketplace for an undisclosed sum to lender J. Safra.
The ones that got away
Looking to grow
“The market is so ripe,” Ashkenazy told Crain's. “It’s the most attractive I’ve seen in a long time.”
— Ben Ashkenazy in 2025
The market is so ripe. It’s the most attractive I’ve seen in a long time.”
Ashkenazy's entire portfolio, estimated to be worth $10 billion, includes hotels, retail and housing.
Ashkenazy's properties
625 Madison Ave.
635 Madison Ave.
Union Station, Washington, D.C.
Faneuil Hall Marketplace in Boston
The developer owns properties across the country.
The Plaza hotel
700 N. Michigan Ave., Chicago
South Station, Boston
Residence of the Little Nell, Aspen, Colorado
The Shops at the Bravern, Seattle
Shops at Rivercenter, San Antonio
9570 Wilshire Blvd., Beverly Hills
Ben Ashkenazy
Buck Ennis
Buck Ennis
Buck Ennis
Bloomberg
— Ben Ashkenazy in 2025
“The market is so ripe. It’s the most attractive I’ve seen in a long time.”
Ashkenazy acquired the land underneath this 17-story Midtown office building in 2013 for about $400 million. He defaulted on its mortgage in 2021 and lender SL Green moved to seize the property. SL Green then sold it for $632.5 million to Related Cos., which plans to build a new luxury apartment tower on the site.
Ashkenazy acquired the land underneath this 150,000 square-foot Midtown tower in 2008 and held it until last year, when lenders foreclosed after he defaulted on the $90 million mortgage.
Ashkenazy acquired the rail hub’s ground lease in 2007 and defaulted on more than $400 million in loans in 2020. In 2022 Amtrak moved to seize the property via eminent domain. Ashkenazy fought, but a federal judge ruled against him. He is now appealing the matter.
Ashkenazy Acquisition
Photos courtesy Ashkenazy Acquisition