Ben Ashkenazy

Ashkenazy has not let the challenges of the past few years dampen his ambitions.

The “shy billionaire” has amassed a $750 million war chest from his own pockets and those of wealthy investors to buy up distressed retail and hospitality properties over the next two years. In July, he paid $72 million to buy the 374,000-square-foot Atlas Park shopping center in Queens.

This comes after the investor spent the better part of the last four years fighting to hang on to some of his treasured properties.

He lost his Union Station property in Washington, D.C., to the Federal government through eminent domain, and has been fighting with his lender there over his debt. He lost a decade-long battle with SL Green over his office tower at 625 Madison Avenue, and last year settled an epic, four-year battle with his partners the Gindis over their shared investments.

Ashkenazy brushes these losses off, insisting the properties he relinquished represent only a small fraction of his overall portfolio, which includes a piece of the Plaza Hotel and the former Barneys flagship on Madison Avenue.

And the mogul who built a reputation for avoiding the spotlight has come out of his shell: in 2024 he went on stage at The Real Deal’s New York Forum, and last year he sat down with Crain’s for his first on-the-record interview in a quarter of a century.