Gallery was a successful editorial photographer when, in 2010, he found his true calling in Haiti. He had gone there with a volunteer group of photographers and filmmakers from New York City to document the aftermath of the earthquake that took more than 150,000 lives and left more than million homeless, and he came away from the experience changed. “Something happened to me,” he says.

Back in New York, Gallery helped organize an event to aid Haitian relief efforts through sales of pictures he and the other photographers had taken. He went on to publish first book, Tent Life: Haiti, royalties from which were donated to Haitian relief organizations.

“The book got a lot of press and sold out, and for me that was a lesson in how photography can be of great use as tool to generate engagement to help people,” he says.

After Haiti, he stopped looking for magazine assignments. “Before that, I felt like I wasn’t doing what I was supposed to do,” he says. “I thought I was doing the magazine work so I could do personal work, but the assignments were taking up all my time. Haiti was a huge turning point. I decided I wanted to work with organizations that aided victims of natural disasters. After Haiti I felt like I was back on track — that I had a purpose and was doing work that really fulfilled me. I wasn’t making as much money, but I felt so much more happy about what I was doing.”

Gallery’s second book, like his first, resulted from a disaster-relief effort. In 2012, after Hurricane Sandy hit the New York City area, he organized an exhibition featuring pictures taken by 20 photographers, himself included, who had documented the aftermath of the storm using what was then a breakthrough journalistic tool — the iPhone. Sales of the images raised some $20,000 for rebuilding efforts; the follow-up book, #SANDY, was released a year after the storm.

Gallery’s third book, just released, returns his focus to the Caribbean, which you might call his second home, after New York. Or you might call it his first home, since he has spent much of his time there since graduating from New York University in 1997. Eight years ago he was living in Trinidad and shooting high-priced real estate throughout the region for the New York Times, and while working in Curacao he discovered the oldest Jewish synagogue in the Western Hemisphere.  

“It was from back in the 1700s, with sand-covered floors and hundreds of candle-lit brass chandeliers,” Gallery says. He later discovered other historic synagogues on Barbados and in Suriname.

A year later, after viewing the destruction he’d seen in Haiti, including that of the grand Cathedral of Our Lady of the Assumption in Port-au-Prince, Gallery decided he needed to photograph the synagogues.

“I realized this is what I’m supposed to do. I didn’t want to only photograph the aftermath of disasters,” he says. “I wanted to photograph the beauty of these synagogues before something happened to them.”

History Hidden From View

The new book, Jewish Treasures of the Caribbean: The Legacy of Judaism In the New World, is a journey through time. Gallery shot synagogues and historic sites in 10 locations — Aruba, Jamaica, Nevis, St. Croix, St. Eustatius, St. Maartin, and St. Thomas, as well as those in Curacao, Barbados, and Suriname.

“The project combined all these things I’m interested in,” Gallery says. “Both my parents are architects, so I’m interested in architecture, and I’m of Jewish descent, so the history was intriguing to me.”

That history is not widely known. It was in the 1600s that Sephardic Jews fleeing the Spanish and Portuguese Inquisitions made their way to the Caribbean, by way of Amsterdam and Dutch colonies in Brazil. Jewish communities at one time were powerful, shaping the economy of the region, but they eventually dwindled and now face extinction. Gallery’s book features essays tracing the history of Jews in the Caribbean by Dr. Stanley Mirvis of the Hebrew University of Jerusalem and Jonathan D. Sarna of Brandeis University.

Gallery found many of the sites he photographed by talking with local leaders of Jewish communities, and also by working with Rachel Frankel, a New York architect who has studied and documented historic Jewish sites throughout the Americas.

“I moved to Jamaica for two years to work on the project, and a local historian there introduced me to her,” he says. “I helped her by doing some of the photography she needed, and she took me along on a tour to various sites on the island.” Gallery shot most of the architectural sites with a Canon 5D Mark III DSLR using 17mm and 24 tilt shift lenses to control perspective. His photographs capture both exquisite detail and a sense of the mystery lingering in these spiritual places.

In some cases, he documented a history that has been hidden from view:  In the Jamaican town of Savannah La Mar he and Frankel uncovered Jewish cemetery after finding a 10-inch stone slab buried in a woman’s back yard.

Making Art History With a Super Pac

Gallery, who is from Philadelphia, discovered the Caribbean as a photography student at New York University. He and some friends took a trip to Costa Rica, and he became fascinated with the people and cultural history of the country’s Caribbean coast.

The next year, after he’d graduated, Gallery began exploring elsewhere in the region, first with an NYU grant and then a Fulbright Fellowship to photograph spiritual sites in Trinidad. He ended up living there for two years. His break as a professional photographer came when his photographs from the island earned him a spot on the PDN 30 list of emerging photographers in 2000.

He still spends about half of his time in the Caribbean. Last year, though, he took a break from work on his new book to help launch an art project in the US that ended up making news: Gallery joined with photographer and conceptual artist Hank Willis Thomas and video artist and activist Eric Gottesman to organize a political action committee — the first-ever artist-run super PAC.

Named For Freedoms  (after Franklin D. Roosevelt’s 1941 “Four Freedoms” address), the super PAC raised money to create advertising based on various types of artwork calling attention to issues such as gun control, racism, gender equality, reproductive rights and free speech.

One billboard in Mississippi featured photographer James "Spider" Martin’s famous 1965 photo of civil rights protesters confronting state troopers in Selma, Alabama. Superimposed over the image was Donald Trump’s campaign slogan, “Make America Great Again.” The billboard managed to provoke both pro- and anti-Trump voters.

“Our goal was to stir up political conversation, and we had good success at that,” Gallery says.

Officially the super PAC was not backing any particular candidate in the 2016 presidential election. It might not be entirely wrong, however, to see it, at least on Gallery’s part, as an attempt to head off a political disaster in the making. After the US was hit by Trump’s political hurricane in November, he and his collaborators were left wondering what to do next.

They’re working on answers now, in part through a residency at MoMA PS1  in New York that will run through the first 100 days of the Trump presidency. “We’re using it as a laboratory to figure out how the Four Freedoms model can be used in different ways,” Gallery says. “I think artists are ready to take a strong political stand in the next four years. I think they’re already doing it.”