I felt relieved. I hoped no more tests were coming my way, but Ms. Bailey kept going. “Let’s say I took away your house key and you had to sleep outside,” she said. “A man from the city comes over and counts you as ‘homeless.’ What would you say?”

“Umm.” This one seemed even harder. “I’d say you’re wrong. I have a place to stay, so… no! I’m not homeless!” I thought I had nailed this one.

But she looked exasperated at my answer. “Wow, have you ever had to do anything for yourself?” she said.

I was at least smart enough to know that she wasn’t literally asking me to reply.

“If I took your house key away,” she barked, “what does that make you?” She leaned across the desk, and I could feel her breath on my face.

“Well, I guess you robbed me. So I’m not homeless, I’m a victim.”

“Okay, we’re getting somewhere. Now let’s say I tell the police to stop coming to your block and to go only where I live. And then I write that you live in a crime-infested neighborhood, that there’s more crime on your block than mine. What would you say?”

“Well, I guess I’d say that it’s not really fair because you have all the police, so-”

“Mr. Professor, we’re really getting moving now!” Ms. Bailey threw up her hands in mock celebration. “Okay, so let’s go back to the original question. You want to understand how black folks live in the projects. Why we are poor. Why we have so much crime. Why we can’t feed our families. Why our kids can’t get work when they grow up. So will you be studying white people?”

“Yes,” I said. I understood, finally, that she also wanted me to focus on the people outside Robert Taylor who determined how the tenants lived day to day.

“But don’t make us the victim,” she said. “We’ll take responsibility for what we can control. It’s just that not everything is in our hands.”

Our subsequent meetings were much the same. I would walk in to discuss an issue-the 60 percent dropout rate, for instance, among the project’s high-school kids. “Research today says that if kids can get through high school, they have a twenty-five percent greater likelihood of escaping poverty,” I said, as if giving a lecture. “So early education-keeping them in school-is the key. Also-”

Ms. Bailey interrupted. “If your family is starving and I tell you that I’ll give you a chance to make some money, what are you going to do?”

“Make the money. I have to help my family.”

“But what about school?” she said.

“I guess it will have to wait.”

“Until what?”

“Until my family gets enough to eat.”

“But you should stay in school, right?” she said, sarcasm rising in her voice. “That’s what will help you leave poverty.” She paused. Then she smiled triumphantly and made no effort to hide her patronizing tone. “So… you said you wanted to talk with me about high-school dropouts?”

It took a while, but I eventually realized there was no point in trying to act even remotely authoritative around Ms. Bailey. There was part of me that felt like the expert researcher, but only a very small part. Once I learned that there was no way around Ms. Bailey’s Socratic browbeating, I decided to give in and just let her teach me.

I usually dropped by her office during the hours she reserved for open visitation from tenants; otherwise it could be hard to track her down. When a tenant came by, Ms. Bailey would ask me to step out. Our longest conversations, therefore, rarely lasted beyond fifteen minutes. Ms. Bailey remained formal with me, as if she were keeping her guard up. She never shared details about specific tenants; instead she spoke in generalities about “families who live around here.”

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.