Real Estate’s Rags-to-Riches Legends Present Uniquely American Tales

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Stuart Elliott

It’s a tale of not-quite-rags to riches, followed by real estate rumbles.  

In our cover story this month, we recount how billionaire Ben Ashkenazy got his precocious start in the business at the age of 17, when he reputedly did a $2 million deal for a shopping center in the Bronx.  

As a youngster, the Israeli emigré traveled across the U.S. with his family in a van, staying in budget hotels with other tourists. A tour of historic Boston brought him to Faneuil Hall, the bustling marketplace. On a class trip to Washington, D.C., Ashkenazy saw Union Station. 

He would later buy both. Now he is in a billion-dollar battle with the government over Union Station, after the feds seized it through eminent domain last year. And he has been blamed for allowing Faneuil Hall to fall into disrepair. And for pushing iconic department store Barneys out of business. All while he’s going toe to toe with New York’s largest office landlord. 

So goes the third act for the so-called “shy billionaire,” who generally flies under the radar despite his 15 million-square-foot portfolio. Check out the great profile by Rich Bockmann (which includes hiring Drake to perform at a bat mitzvah and driving around a Porsche 911 in Houston in the 1980s).  

The Ashkenazy story is one of six in-depth profiles of real estate players in these pages — the most I can remember having in one issue.  

Besides making for great beach reading, I realize there is something uniquely American about the profiles we write, an ethos that also carries through to last month’s cover story about tycoon Joe Chetrit and our new book, “The New Kings of New York” (buy it here, if you haven’t already).  

Horatio Alger’s ubiquitous “rags to riches” legend has become one of the foundations of American society — anyone can succeed and achieve material prosperity through hard work.  

Once you add in the rumbles and battle royales at the top of the food chain, there is a straight line from that tradition to F. Scott Fitzgerald’s “The Great Gatsby” (or Sinclair Lewis’ “Babbitt” or Theodore Dreiser’s “The Financier”) down to more recent tales such as “The Wolf of Wall Street” and “Succession.”  

These stories are so different from anything in the European realm. When you think of authors like Trollope or Balzac, the Brontës or Proust — they don’t seem to relish scrappy entrepreneurship in quite the same way. 

As associate publisher Hiten Samtani told me, if you think of real estate titans as the new robber barons, The Real Deal is telling stories of American ingenuity and enterprise, warts and all.  

So anyway, something uniquely American to celebrate this Independence Day. 

Our other profiles in the issue span the country.  

We take a look at Michael Reschke, the developer who has been called the Harry Houdini of Chicago real estate and is facing his latest challenge.  

And in Los Angeles, as developer Rick Caruso runs for mayor, he has pledged to put his company — one of the nation’s largest privately held real estate companies — into a trust if he wins. We look at Corinne Verdery, the CEO-in-waiting.  

We’ve also ranked the most active developers in New York, who are staring down interest rates and recessionary headwinds, plus dealing with (or dodging) the city’s increasing red tape. 

Brokerages, too, are shedding staff and warning of slowing sales as a darker outlook looms over the housing market.  

It’s enough to make you want to head to the beach. So kick back with these pages and enjoy the summer.



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