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I’ll never forget the Upper West Side moms of my sixth-grade class chuckling amongst themselves while purposefully mispronouncing 50 Cent’s name as “Fiddy.” But as quickly as that early fad in rap music came, its honeymoon at my school was over. On the after-school bus heading downtown, the sound of 50 Cent ringtones disappeared.

Yet something about the hip-hop aesthetic touched me. Every day after school in sixth grade, I dragged my best friend on a long stroll through the nearby Frederick Douglass public housing projects, where someone was usually sitting on a bench playing 50 Cent from a stereo. And so on my way back to Yale’s campus from Union Station during my freshman fall, curiosity welled up in me each time I passed by the housing development called Church Street South. I wondered what went on just past the convenience store, where the path is hidden from view by the oddly angled buildings.


To find out, I first needed the name of the hip-hop clothing store that served as the backdrop for local online rap battles. I was working on an article about New Haven hip-hop for The Yale Herald. I was looking for a way to understand the city, and the underground hip-hop scene seemed like a good place to start. After guessing the wrong store, it took a day of trudging through New Haven and West Haven to find a contact who could help me. Finally, a few days later I hopped off the Dixwell Avenue bus at the intersection of Dixwell and Henry, a desolate corner surrounded by abandoned storefronts about seven blocks north of Payne Whitney Gym.

I had been told the store’s name, Fun City, but there was no sign indicating it anywhere. Finally I saw a tiny “open” sign in a window next to photos of famous rappers. The burly man I had come to meet, Twan “Cuzin Twiz” Singleton, had to come unlock the door, and I received a hearty greeting as he invited me in.

The store was mostly empty except for CDs, videos, and the computers that he uses to edit Cuzin Twiz TV, an occasionally vulgar documentary-style series that airs on Citizens Television. In one of the videos, a local rap battle between two not-very-sober individuals devolves into a brutal beating. After seeing the video, I was nervous to meet the man who had videotaped the exchange.

As soon as we started the interview, however, I felt at ease. He spoke boisterously of the broad problems facing young men in New Haven, and both the positives and negatives of hip-hop’s prevalence. All my fear was overcome by his charisma.

While it may just have been his disinterest in details, I did get the sense that Twiz was being careful about secrets. He claimed hip-hop artists from different neighborhoods didn’t have serious disputes, a statement I already doubted based on the videos I had seen. It was only after I slowly accumulated knowledge on the city that anyone was willing to discuss topics like the neighborhood-based violence that often accompanies New Haven hip-hop.

I stayed in New Haven for the following summer interviewing and eventually drinking with some of the city’s best-known local rappers. I would interview one rapper, and then ask him to refer me to another. I realized that I had come upon something of a solution to the problems of communication between Yale and the city. The local artists had a vested interest in talking to a journalist since they were trying to get more listeners, more viewers for their YouTube videos. This desire overrode most people’s negative feelings about Yale students. I told everyone that I was a Yale student writing a book about the New Haven rap scene, and only a single artist out of the 27 I approached outright refused to talk to me.

Going from interviewing to hanging out wasn’t a difficult transition. One rapper, perhaps because he pitied me when I misinterpreted the slang word “kis,” slang for kilograms of crack, as actual “keys,” decided to teach me New Haven’s neighborhood handshakes. They’re surprisingly simple greetings that involve smacking hands a certain number of times based on what neighborhood you’re from. Those handshakes alone, which I used at the start of most of my interviews, were usually enough to make my interviewees laugh. After realizing I knew a thing or two about the city, people seemed willing to chill with me, if only so they could tell their friends about the Yale kid who knew the Newhallville handshake.

By the end of the summer, I put the book on hold as I realized my own curiosity was about more than just hip-hop. It was about the whole workings of inner-city New Haven — the neighborhoods, the economy, the violence — in a way that certainly encompassed music, but also went beyond it. Just hanging out with locals and learning the city’s workings seemed like the right way to proceed.


Hugh “H.G.” Gallman was the first close friend I made in New Haven, and the first person I didn’t have to interview to get to know.

We spent more and more time together when I was helping start a student group called Middleman that connects Yale students with New Haven residents they wouldn’t otherwise meet, either for projects like interviews and photo shoots or simply to hang out. H.G. helped us take students around neighborhoods, and he introduced us to major underground players in New Haven. In October 2011, he gave a lunch lecture to Urban Studies students about the underground economy in the Elm Haven high-rises where he grew up. We shared numerous informal dinners in the Silliman dining hall, and some friends had to swipe him in for me when my extra dining hall swipes ran low.

Meanwhile, he asked me to write a recommendation for him on Silliman College stationery, since he was involved in a legal battle regarding narcotic sales. This was a big secret between us — I wrote the letter, but I still didn’t know much about it.

I spent so much time with H.G. that I grew accustomed to his default expression: a blank grimace that would quickly transform into a hearty laugh, then back to a grimace with no expression in between. After a dinner at a dining hall in November 2011, H.G. invited me and a fellow Yale student to hang out at his place. I admit I felt a bit surprised by how normal H.G.’s apartment was — he had told us stories about selling drugs in the “pissy hallways” of Elm Haven, but his new place was modest and unremarkable. We watched “Homecoming,” a slapstick movie he and some friends had put together about a road trip, on his TV and stereo system. Meanwhile, the three of us sipped on a bottle of Peach Cîroc, a flavored vodka that has gained immense popularity in New Haven.

At the end of the night, H.G. drove us back to Yale at wildly high speeds in his Honda Accord, and as we approached Broadway, H.G. asked me and my friend what we thought of him. I was surprised by the question, and muttered something inadequate about not knowing him well enough to respond.

Three days later, H.G.’s friend told me that H.G. had been arrested. There was still a lot I didn’t know about the narcotics charge. I was left with the task of informing Elmseed Enterprise Fund, a Yale microloan organization to which I had connected H.G., that he wouldn’t be able to continue with the application process due to his incarceration. I never got a chance to give him a better reply to his question before his arrest, but I was honored he felt comfortable enough with me to ask.


Despite my relationship with H.G., I was still very much a Yale student. Rappers saw me as such, and wanted me to return their hospitality by giving them a glimpse of campus life.

One rapper, Jay-Quan “J-Dice” Dixon, was particularly enamored with the idea of partying on campus. So I invited him and his friends to join me on campus at a rap battle in September 2011 between Jacob Sandry ’15 and myself. I figured J-Dice and his friends would get a kick out of seeing two Yale students attempt something resembling hip-hop on the first floor of the Alpha Epsilon Pi house.

After the battle (which I lost after stumbling on a line), J-Dice freestyled for some friends of mine, but his sexual puns were vulgar enough to alienate most Yale students. As the party developed, J-Dice’s cohort seemed frustrated by the difficulty they had attracting Yale girls’ attention. The party was quickly becoming awkward for us.

Things got tenser later when J-Dice invited two high-ranking members of Klean Up Krew, a group that almost a year later was the target of a federal investigation which culminated in 105 arrests. The two men — Ronald “Kiki” Bidon and a man named Skeem whose real name I never caught — were shocked to discover it was a Yale party. When Skeem heard about my journalistic interest in local hip-hop, he started interrogating me about how much I knew about street politics.

I felt I should have known the evening would be awkward, and I worried the encounter could have been dangerous. Still, I was proud that I had made such an unlikely encounter possible.


The night of Sept. 14, 2012, I was planning to go with a few members of Middleman to a Newhallville fundraiser party for a charity group called Ice the Beef, for which I sit on the Board of Directors. Ice the Beef was started by Darrell Allick, a man I met through H.G. who has since become one of my closest friends, to help youth avoid the path of “guns and drugs” that he himself went down.

That evening, one of the members of Middleman was sick, and another wasn’t picking up his phone, so that left me and my friend, Victoria Sanchez ’13.

When we arrived at the house in the Ville, we were escorted to the basement, where there was a makeshift bar set up and a small crowd that was gathered around and taking shots. Cups of delicious Ice the Beef Punch were going around. I exchanged warm embraces with the Ice the Beef ladies, as Darrell likes to call them, who make up the bulk of the team.

Shortly after, Darrell came over to me smirking, and the questioning and pressure began. Besides trying to stop gun violence in New Haven and raise his three children, Darrell has decided he wants to find me a girlfriend. If subtlety were his strong suit, this plan would be fine, but he prefers discussing his designs in a more transparent fashion.

I tried to explain the situation to him — Victoria and I were just friends. She was interested in New Haven so I had invited her to tag along. I only prayed the blaring music made Darrell’s questions about who my “shorty” was less audible. I also hoped she didn’t understand his designs when he ushered us into the so-called V.I.P. lounge, two lonely chairs a few feet away from the bar.

As we chatted in the lounge, I couldn’t help but feel like I had made progress from where I started. We had come to one of the more notorious neighborhoods of New Haven to a party to which I had been personally invited. I knew at least a quarter of the people there, and it was easy enough to strike up conversation with the people we didn’t know.

I’m starting to enjoy Ice the Beef parties as much as Yale ones, and I’m starting to consider myself a New Haven resident as much as a Yale student. Darrell feels comfortable sharing secrets with me, like the details of the narcotics operation that made him famous in this city. And I feel comfortable letting him into my own life.