Sudhir Venkatesh - Gang Leader for a Day

After a few months of this, I told J.T. that I was frustrated by my interactions with Ms. Bailey. I couldn’t tell if she trusted me.

J.T. enjoyed seeing me struggle. He had warned me that getting to know her wouldn’t be easy and perhaps wasn’t even worth trying. “It took a while before I let you talk with my boys,” he said.

“What makes you think she’ll just walk you around and show you everybody? Things don’t go so fast around here.”

He had a point. If Ms. Bailey needed time to feel comfortable with me, then I would just have to wait.

As the Chicago winter began to settle in, Ms. Bailey asked me to help her with a clothing drive. Tenants and squatters in her building needed winter coats, she said, as well as blankets and portable heaters. She wanted me to collect donations with her from several stores that had agreed to contribute.

A friend of mine let me borrow his car, a battered yellow and brown station wagon. When I went to collect Ms. Bailey at her building, she was carrying a large plastic bag. She grunted as she bent over to pick it up and again as she set it down on the floor of the car. With labored breaths, she directed me to our first stop: a liquor store a few blocks from her building.

She instructed me to drive around the back. She told me she didn’t want the manager to see me, but she didn’t explain why.

I parked in the alley as Ms. Bailey went inside. Five minutes later a few employees came out the back door and began loading the station wagon with cases of beer and bottles of liquor. Nothing expressly for winter, I noted, although a stiff bourbon could certainly help take the sting off the Chicago cold. Ms. Bailey climbed into the car. This donation, she told me, was made with the understanding that she would direct her tenants to visit this liquor store exclusively when they needed booze.

We drove a few miles to a grocery store on Stony Island Avenue. We went in the back way and met with a man who appeared to be the manager.

“Hey, sweetheart,” Ms. Bailey said. She introduced me to Mr.

Baldwin, a large, pear-shaped black man with a round face and a wide grin. He had a clipboard in his hand, marking off the sides of beef hanging from a ceiling rack.

Mr. Baldwin gave Ms. Bailey a hug. “I got what you want, babe,” he said. “All in the back. I got them ready for you yesterday.”

He pointed us toward a younger man, who led us over to a few big garbage bags filled with puffy black jackets. At first glance they looked exactly like the jacket the young man was wearing, which had the name of the grocery store prominently displayed on the sleeves and chest. Were they the same jackets? I wondered if Ms. Bailey’s tenants would wear clothing with a grocery store’s name on it.

As I hauled the bags to the car, Ms. Bailey shouted at me. “And bring three cases of beer in here, Sudhir!”

I did as I was told. Even I, middle-class naïf that I was, could sense a horse trade.

Back in the car, Ms. Bailey anticipated my question. “I know you’re wondering what we were doing at the food store,” she said. “Take a look at the jackets.” I reached into the backseat and grabbed one. It smelled distinctly of bleach, as if it had been disinfected. The store’s patch had been either removed or covered up with another, even larger patch. It read ROBERT TAYLOR PRIDE.

Ms. Bailey smiled. “Those jackets are warmer than what most families can buy in the stores. These workers are sitting in a meat locker all day, so you know they have to stay warm. The manager donates about twenty to me each Christmas.”

“And the patches?” I asked.

“The guy who makes the jackets for him does it for free-for us.”

“And the beer?”

Ms. Bailey just smiled and told me where to drive next.

We hit several more stores that day. At Sears, Ms. Bailey exchanged pleasantries with the manager, and they asked about each other’s families. Then he handed over a few boxes of children’s coats; Ms. Bailey directed me to put the rest of the beer in his car. At a dollar store, Ms. Bailey traded some of the liquor for a bundle of blankets. At a hardware store, Ms. Bailey gave the manager the heavy plastic bag she’d brought along, and he gave her three portable heaters.

“Don’t ask what’s in the bag,” she told me as I carried the heaters back to the car. “When I know you better, I’ll tell you.”

Only once did Ms. Bailey receive a donation that was actually a donation-that is, something for free. At one grocery store, she got some canned food without having to exchange any beer or liquor.

By the time we finished, we were on the far southern edge of the city. We hit traffic on the drive back to Robert Taylor, which gave me the opportunity to pepper Ms. Bailey with questions.

“When did you start doing this?” I asked.

Ms. Bailey told me that she had grown up in public housing herself. Back then, charities, churches, city agencies, and individual volunteers all helped out in the projects. “But the volunteers don’t come around anymore,” she said wistfully. “Have you seen any of those nice white people since you’ve been around? I didn’t think so. Nobody gives us money, nobody runs programs. Not a lot of people are doing the free-food thing anymore. Even the churches really don’t do what they did in the past.”

“But I don’t understand why the people we saw today want to give you things. I mean, how did you get to know them?”

“Well, first of all, most of them grew up in Robert Taylor or they have family in the projects. Lots of middle-class people don’t like to talk about it, but they came from the projects. It’s easy to forget where you came from. But I try and remind these people that they were once like us. And a few times a year, they do the right thing.”

“So why give them beer and liquor?” I asked. “If it’s a donation, it should be for free, no?”

“Well, things ain’t always that simple,” Ms. Bailey said. She brought up the incident I’d seen some months back, when the woman named Boo-Boo wanted to kill the Middle Eastern shopkeeper who’d slept with her teenage daughter. “That’s what a lot of women have to do around here to get some free food,” she said. “I don’t want to see it come to that. So if I have to give away a few bottles of gin, that’s fine with me.”

Back at her office, Ms. Bailey organized the winter gear and prepared large baskets filled with canned food and meat. Word spread quickly, and families from her building soon began to drop by. Some were shy, others excited. But everyone seemed happy, and I watched as children smiled when they tried on a new coat or a warm sweater.

I noticed that some people received food but no clothing. Others got a jacket but no food. And some people just stood around until Ms. Bailey told them, “We don’t have anything for you today.” She said this even though the food baskets and clothing were in plain view, so I didn’t know why she was withholding the gifts from them. Did she play favorites with some families?

One day Clarisse, the prostitute, walked into Ms. Bailey’s office. There were several women already in front of her. Ms. Bailey’s assistant, Catrina, was writing their names and noting exactly what each of them received.

“You got something for me today?” Clarisse asked, a lilt in her voice. Then her eyes landed on me briefly, but I didn’t seem to register. She smelled like liquor; her blouse was undone so that one of her breasts was nearly popping out. Despite the cold weather, Clarisse was wearing a black miniskirt and sliding around perilously on high heels. Her face looked vacant, and her mouth was frothy. I had never seen her in this condition before. She had told me herself that she didn’t do drugs.