The fall of the Berlin Wall led Eskenazi out of Queens into the larger world. After trips to Germany and Romania for their first democratic elections he traveled to Russia in 1991, just before the August coup that marked the end of the USSR, and has returned many times since culminating in a photography book project called Wonderland: A Fairy Tale of the Soviet Monolith, winner of Best Photography Book 2008 by Pictures of the Year International.
In 2004 he received a Fulbright Scholarship to return to Russia to make a series of large format color portraits called Title Nation with a Russian colleague which will be published Fall 2010.
Jason Eskenazi has received numerous awards including a Guggenheim Fellowship, 1999; The Dorothea Lange/Paul Taylor Prize, 1999, for his work in a Jewish Village in Azerbaijan; and The Alicia Patterson Foundation Grant, 1996. His work has appeared in many magazines including Time, Newsweek and The New York Times and Soros Foundation publications.
In 2004 -2005 Eskenazi organized a Kids with Cameras workshop in the old city of Jerusalem, teaching photography to Arab Muslims and Jewish children, which toured many U.S. cities.
For economic reasons as well as to obtain health insurance Eskenazi took a job as a Security Guard at the Metropolitan Museum of Art from March 2008 – Nov 2009. He created and co-edited a new independent magazine for the guards called SW!PE which received a lot of media attention. And also created the Americans List.
Eskenazi quit the museum and used saved funds in order to continue photographing for his next project The Black Garden set in the geographical locations known to the ancient Greeks, investigating the east-west divide, while basing himself in Istanbul. He was also the International Curator/ Creative Director for the Bursa Photo Fest for its first 2 years.
He is also a co-founder and editor of DOG FOOD, a newspaper blending Cynic Philosophy and Photography.