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A Life-Changing Day: The Homeless… in New York… in Winter

Chapter 2: The Homeless in New York in Winter

My epiphany about how vulnerable I am—and how vulnerable we all are, when you get right down to it—came unexpectedly on a bitter cold day in late January, 2004, in the middle of New York City. Sometimes your eyes open up first…and then your heart.

Like most kids of the age I was then, I took a lot for granted, like my warm house, my room, and my bed. Like a refrigerator always stocked with food I like. Like parents who love and take care of me. I never thought about not having those things. They were just always there. But what if, someday, for some reason, things changed, and the people who loved me weren’t there for me? What if I found myself cold, hungry, and alone? If that could happen to someone else, why could it not possibly happen to me?

It was one of the coldest days of the year. Bruce had invited me to accompany him on a personal outing. It was nothing official, so we didn’t need press passes. Bruce has a special interest in photographing homeless people, and that was what we were out to do together: look for homeless people to photograph. I didn’t know whether he was planning to do a book of pictures of the homeless, or just what was behind his interest, but I have always been enthusiastic about photography outings with Bruce. One of the things I like about photojournalism is that you never know what great pictures you might get to take. If you’re lucky, you see something unexpected, and then, if you’re fast and know what you’re doing, you get a chance to capture that moment forever.

Up until this particular day, I honestly thought that was all there was to it, that you find a great subject—a person, animal, bird, or some great scene… whatever you want to shoot. Then you set up your shot and take it. After that, you just look around for your next shot. In this scenario, you’re not part of the picture; you’re the outsider, the observer. This day, I was going to be a lot more, but I didn’t know it yet.

The weather was brutal. The wind was howling like a banshee, and the few people on the streets were bundled up like Eskimos. Mounds of snow had been plowed to the sidewalks and were freezing into dirty walls of ice. Where I live, outside the city, the streets are always quiet and deserted, and when it snows, the big lawns become rolling hills with the pure white snow piling higher and higher, like layers of cotton sheets. Snow looks wonderful when you watch through your window as it comes down, a fire crackling behind you and a cup of hot cocoa with marshmallows in your hand.

But that day I was not in my cozy living room but out on the icy city streets, trying to stay warm and not fall on the ice and slush. I had my JanSport backpack on, and inside it was an extra sweatshirt and the $20 bill my parents had given me to buy lunch. I also had my Canon Digital Rebel camera ready and had set my ISO number to 200.

I’d never thought much about homeless people, for no reason except that to me they were subjects, like interesting buildings, landscapes, and anything else that offered a good composition. I wanted to find a few homeless people, take their pictures, and get out of the brain-numbing cold. I wasn’t even sure we could find anyone because it was so bitter cold out.

Besides the bus and truck fumes, which were not so great, there was something in the air that smelled outrageously delicious and made my mouth water. It was the aroma of my favorite treat, candy-coated peanuts coupled with the famed hot dogs of New York’s street vendors. I could also smell the hot pretzels and the shish kebabs being offered by other pushcarts. These men were also bundled up and probably wishing, like me, that they were somewhere else. I snapped a few of them as a substitute for the homeless who, I was quite sure, were all in shelters, churches, or soup kitchens. Nobody could survive long on these streets, I thought. I didn’t say anything to Bruce about it, though. He was still quite intent on finding them.

The smells from the carts and the cold itself had made me really hungry. I asked Bruce if we could eat, and we walked a few blocks over to one of my favorites, the Gemini Diner on Second Avenue and 35th Street. I happily anticipated a juicy hamburger and crispy french fries, but a “CLOSED FOR VACATION” sign was on the window. We would have to look elsewhere. Bruce said we should head back uptown, so we did. Along the way, I snapped photos of the towering skyscrapers. I liked how they looked in the stark winter light. I was still on the lookout for homeless people, yet still not expecting to find any.

As we made our way north, I stopped to take photos of discarded Christmas trees, closed shops, and the various passersby. The challenge in photography, according to Bruce, is to get the right picture at the right time. That’s what I was trying to do. But frankly, it was getting more difficult as my fingers were now pretty numb, even through my thick leather gloves.

Then I finally spotted a homeless person. Actually, I almost fell over him! He was lying down in what appeared to be an old refrigerator box and had covered himself with some raggedy blankets and dirty coats. The box rested on a pile of snow. This all made for an interesting shot, framed with the people walking around the box, not even noticing the human being inside it.

The sun had disappeared through the drifting clouds, and the temperature had dropped even lower. As I held my camera in front of me like a shield of invisibility, these thoughts entered my mind: How can anyone survive living outdoors in weather like this? Doesn’t this person have any family? How can this be allowed? Who gets blamed if he freezes to death out here?

I felt a little funny about leaning over the box with the camera in front of my face, but I wanted to see if this man was wearing anything warm. I was scared, but I edged closer. I could see that he was wearing a Yankees baseball cap, a white cotton t-shirt, ripped blue jeans, two muddy coats and dirty green boots. I didn’t see any food near him, and he sure didn’t smell good. I’d been looking all over for homeless people to photograph. Now I’d found one, and all I could think of was what I could do to help him. But I didn’t know what to do. Should I ask him if he needed help? Would he be drunk, crazy, or even violent? My thoughts were in a whirl, like the snow that was still coming down, and I also didn’t know what to say to Bruce, who was walking around the man, taking shots from different angles.

Looking across Fifth Avenue, I noticed a small Dunkin’ Donuts shop. I put my camera back in my backpack and made sure I still had the $20 in lunch money. Entering the store, I inhaled the coffee and donuts. It was comfortable in there, with the steam from the radiators giving off a blanket of warmth. I went to the counter and asked the clerk, “Can you please give me $20 worth of doughnuts and include two hot chocolates?” She brought my order, and I handed her the money. Hands full, I ran back to Bruce and handed him one of the steaming hot chocolate drinks. I told him the doughnuts and the other hot chocolate were for the man in the box. Bruce stared at me. “What are you doing?” he asked. “Well, I feel bad for this man here,” I said. “I can sure spare a meal, and he can use it. Let this man enjoy…something.” I bent down and put the box on the sidewalk, next to the man’s head, and asked him if he would like some hot chocolate.

Startled, the man looked up at me like he had awakened from a dream. Now that I was closer, I noticed that he had a long, dirty white beard. He also had dirt all over his face. As he stared at me, I noticed he was missing his right arm. Where that arm should have been there was an empty sleeve. With his left arm, he slowly opened the pink and orange box of doughnuts, like it was Christmas and he was a boy who had just gotten the best present under the tree. His surprisingly youthful blue eyes began to water. Then he put the box down with his one hand. He looked at me and said, “God bless you and your family, boy.”

I had not noticed till now that a few people had stopped and gathered around us. They were staring at me and the man, who was hungrily wolfing down his doughnuts while taking delicate sips of his hot chocolate. That made me smile, but I wanted him to have some privacy, and a few minutes of forgetfulness, perhaps. I hoped the others would go on their way too, unless one of them had a way to help him that went beyond staring.

I said goodbye to the man and walked away, with Bruce alongside me. “Richard, that was the greatest thing I have ever seen any kid do,” Bruce said. That made me feel really good, but I knew I was certainly no hero. What could I or anyone really do to help this homeless man who was lying in a filthy, flimsy cardboard box on a pile of dirty snow on a sidewalk in the middle of winter in the greatest city on earth? I still wish I could have done more for him. For the moment, I had to take satisfaction from doing even that small good deed, what my religion calls a “mitzvah.”

As we headed away into the darkening twilight, I realized that I had not taken a single photo of the man. When I thought about it, I realized that taking photos of that homeless man had not seemed as urgent once I stopped thinking about the “story” his picture might tell. Then I started thinking about the man himself, wondering what his story was, and how he wound up lying in the street, with one arm missing, and nobody noticing his misery or doing anything about it.

When I discussed my thoughts with Bruce, he said that the more I saw my subjects as real people, and the more insight I developed into the “what” and “why” of their lives before I captured them with my camera, the better I would get, not only as a photographer, but also as a man.

I didn’t totally understand what Bruce said, but I thought about it, and about my experience with the homeless man.

It definitely gave me a lot to think about. And I never take anything for granted anymore.

This is a chapter from the book: Apprentice! Lessons Learned on the Frontlines of Life by Richard Liebowitz. A nationally recognized copyright attorney Richard Liebowitz fights for the rights of photographers around the world. Learn more about his firm at and how their copyright lawyers may be able to help you.