By: Jake Haddock

       On a frigid Friday night in December, I walked around as I kept an eye out for people I could interview for their stories. After walking up and down Hanover street many times to no avail, I decided to call it quits for the night and head back home. I walked along the windy backstreets and came upon Hull street. I sharply turned the corner and immediately noticed an older gentleman with an easel, paintbrush and a canvas. After a few minutes of quietly watching him paint,  I approached the man and introduced myself, explaining that I was interviewing people for a project. He told me that he would be glad to help out, after he had finished for the night. We agreed to meet at Caffe Paradiso at 10pm later on.

      At 10 pm sharp, the man walked in and hung up his peacoat. He introduced him self as just “Rocky” and took a seat. He asked if I minded ordering him a cappuccino, so I did. After we sat for a few minutes and quietly drank our beverages, I asked him what he did for a living. He responded that he was homeless and was between jobs at the moment. “I’m 54 years old and I don’t have a job. That might make you feel bad for me, but don’t. I’m happy.” Rocky then explained to me that he sometimes stays at shelters, but for the most part, he sleeps on park benches or at his friend Ricky’s place. He told me he hd been good friends with Ricky for years and that the two helped each other through a lot. I asked him about his work and he explained that painting was his source of income for him at the moment. “I’ve been painting for over 25 years now, I started doing it as a way to calm myself, now I do it because it passes the time.”

     “I grew up here in the North End. I lived here since 1979. I moved to Buffalo in 1990, but came back in 2001. It’s where I have spent most of my life, you know. My Mother was also a painter, but back in the day,  she put it aside to raise me and my brothers.” Rocky went on to explain that he was a construction worker for the “Big Dig”, the most expensive highway project in the United States. A project that greatly impacted how Boston is shaped geographically now. “I’ve seen this place (the North End) change a lot over the years.” I asked Rocky what the greatest moment of his artistic career was and he told me it was when he sold his first painting. 

     “I sold my first painting in 2008, a long time after I started doing this painting thing. When I started, I didn’t think about doing it for money, it was just something fun I did. But after I started doing it a while and getting good, I decided why not. Ricky was paying for all my materials at the time and so I thought it would be a good idea to try and find a way to pay him back and help out since he’s done so much to help me. I started working on this painting, not knowing I was going to sell it. Most of my paintings are of places I see around here and this particular painting was of the Old North Church, one of the most popular places around here. I painted this one for a week, going out with my materials every morning. The rest of my paintings usually only take me a day or two but since this was a house of god, I needed to pay it more respect. It took me two or three tries before I got the finished product that I wanted. But afterwards when it was done, I knew it was good and maybe my best painting yet.”

     “At the time, Ricky was getting evicted from his place near Jeffries Point. Ricky’s not a wealthy guy either so that was a tough time for him. Since I was sleeping on the couch at his place a lot and he was helping me out with with materials, I decided to try and sell my paintings to help him keep his place. At first, I tried selling my stuff on the street like you see some people do but that didn’t work out for me since I didn’t have a lot of paintings or business sense. After that, I tried reaching out to my other friends who were artists and who had sold some of their stuff in galleries. These galleries were for homeless people like me who could put their stuff up and if it sold they would split the commission with you. I reached out to those places but was rejected by them too. Eventually it was like 3 weeks of trying to sell these paintings but having no luck. One night, I couldn’t sleep at Ricky’s because he was out delivering pizzas so I had to sleep on the streets. I slept at the wharf and woke up to these two guys trying to take my stuff. They took my big bag that had all my materials in it and some other shit. After that night, all I actually had was my paintings. The next day, I went and got my paintings that I kept at Ricky’s house and went out try and sell them again. This time, I set up near the Old North Church and tried to sell the latest one I painted that I was talking about. It was the painting I liked most so I didn’t try to sell it before but now I needed cash so I did it, you know. It was early in the morning on Sunday and after church got out, the streets were flooded with people like always on Sunday mornings. Lots of people passed me by, looking at my paintings for a little but nobody wanted to buy them. Around 2 in the afternoon or so, a guy came up and looked at my stuff for a while. After a couple minutes, he asked me how much I wanted for the Old North Church painting. I told him to make me an offer. He asked me if $200 was ok and I couldn’t believe it, you know. I told him yes and he explained to me that he collected a lot of art and was visiting from Pennsylvania. He bought it, we shook hands and he walked away. It was the happiest I’d ever been, you know. It wasn’t much compared to the thousands that people make, but it was a lot to me. I gave it all to Ricky. He couldn’t keep his place, but he found another place right after. I’ve sold a few paintings after that but nothing made me as happy as the first time, being able to get paid for working hard on something. It was a good feeling, you know.” 

     After that, Rocky went on to tell me more about his situation now and how he was in a lot better of a place. He was happy on his own and was spending most nights crashing on Ricky’s couch now.  He told me he paints everyday. Once the interview was over, I looked up at the clock and realized three hours had flown by. I thanked Rocky very much for his time and we shook hands and each went on our way. It was amazing hearing about how his painting meant so much to him. The things he overcame and dealt with are incredible and a tribute to what art can do. Rocky paints all around Boston, but spends most of his time in the North End. If you see a humble gentleman quietly painting with his “materials”, it’s Rocky.