seen Scott, Larraine, and Pam and Ned evicted from the trailer park, I began looking for a new place to live on the North Side. One day, I mentioned this to Officer Woo, one of the security guards Tobin had been forced to hire to appease Alderman Witkowski. Woo’s real name was Kimball, but he told everyone to call him by his childhood nickname. A gregarious black man who tried to make friends with everyone in the park, he wore size 6 XL T-shirts and a security badge he had picked up at an army surplus shop.
“You talkin’ about moving out by Silver Spring?” Woo asked, thinking about an area where Milwaukee’s black inner city gave way to the northern suburbs of Glendale and Brown Deer.
“I’m thinking like city center,” I clarified.
“You want to be by Marquette?” Woo asked again, referencing the Jesuit university located downtown.
“Not by Marquette. I’m looking for an inner-city neighborhood.”
Woo squinted at me, assuming he had misunderstood. It took a few more conversations for Woo to realize that I wanted to live on the North Side, in a neighborhood like his, where the street signs were green, not blue like in the suburb of Wauwatosa. Once he did, Woo invited me to live with him in a rooming house on First and Locust. The rent was $400, utilities included. I accepted and paid the landlords: Sherrena and Quentin.
The rooming house was on the second floor of a duplex, white with green trim. Woo and I shared a living room, bathroom, and kitchen, whose cupboards could be padlocked to keep your roommates from eating your food. My room came with a window, draped with a heavy blanket, and a full-size bed, under which I found an empty can of Classic Ice, Narcotics Anonymous pamphlets, toenail clippers, and a typewriter in a hard plastic case. Behind the rooming house was an alley, tagged in rushed Gangster Disciples graffiti, and a small weedy backyard with a cherry tree that, come May, unveiled soft blossoms that looked like a spray of confetti. I lived in the rooming house until June 2009.
Woo had told Sherrena that I was “working on a book about landlords and tenants.” Sherrena agreed to an interview, at the end of which I made my pitch.
“Sherrena, I would love to be kind of like your apprentice,” I said, explaining that my goal was to “walk in [her] shoes as closely as possible.”
Sherrena was all-in. “I’m committed to this,” she said. “You have your person.” She was in love with her work and proud of it too. She wanted people to know “what landlords had to go through,” to share her world with a wider public that rarely stopped to consider it.
I began shadowing Sherrena and Quentin as they bought property, screened tenants, unclogged sewer pipes, and delivered eviction notices, just as I had done with Tobin and Lenny. I met Arleen, Lamar, and the Hinkston clan through Sherrena. Later, I met Crystal through Arleen, and Vanetta through Crystal. Doreen was lonely and happy to have someone to sit and talk with. Lamar warmed to me after I helped him paint Patrice’s old unit; I later sealed the deal by being decent at spades, which I used to play regularly during my days working as a firefighter in college.
Arleen was a much tougher case. At first, she kept me at a distance and would remain silent when I explained my project to her. When I tried to fill the silence, she would cut me off, saying, “You don’t need to keep talking.” Her biggest worry was that I worked for Child Protective Services. “I feel uncomfortable talking with you,” Arleen told me during one of our early conversations, “not because of how you are, but just because of all this stuff that’s happened to me. I’ve been in the [child welfare] system so long that I just don’t trust people anymore.” I responded by saying that I understood, giving her some of my published work—which I had learned to keep in my car for moments like this—and, later, taking it very slowly, limiting myself to only a handful of questions per meeting.
Other people thought I was a police officer or, in the trailer park, a spy for the alderman. Still others thought I was a drug addict or a john. (For a time, Woo and I lived with sex workers in the rooming house.) Sherrena introduced me as her assistant. To Tobin, I was nobody.
Some tenants suspected I