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Published in Print: May 1, 2004, as Great Expectations

Great Expectations

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Drawing from her experiences, Chicago teacher Toni Billingsley pushes students with troubled backgrounds to excel.

Early on a slightly overcast morning on Chicago’s west side, in the basement of a 97-year-old school building, it was already show time for Toni Billingsley. Around her, 19 7th graders who’d only rolled out of bed an hour or so before were crawling on all fours, following her command to meow like lost cats. Billingsley chuckled. "OK, on the count of three, you will no longer be hypnotized," she told them. "Uno! Dos! Tres!" This was Spanish I, Billingsley-style: part introduction to the language, part aerobic workout, part improvisation workshop, and part stand-up comedy routine.

"Señor Jones, levántate!" she called out a few minutes later. A thick kid with a gray hoodie and plaited hair stood up. "Salta y tira la pelota como Miguel Jordan" ("Jump and shoot the ball like Michael Jordan"), Billingsley told him. Señor Jones reluctantly raised one arm in the air and stretched the other out behind him in a half-hearted approximation of Jordan’s celebrated dunking pose. "No es como Miguel Jordan," responded Billingsley, who then took a flying leap across the room and slammed an imaginary basketball through an imaginary hoop. "Eso es como Miguel Jordan."

Without missing a beat, she turned her attention to another student. "Señor Hill," she called out, and a boy with a short Afro and reddish skin tone sat up a little straighter. Billingsley held out a pen in one hand and a pencil in the other. "Toma la pluma," she commanded, and Señor Hill, after a momentary hesitation, took the pen from her. "Ahora, toma el lapiz." He took the pencil. "OK—la pluma besa el lapiz."

"What you say?" Señor Hill asked.

Poker-faced, Billingsley said it again, enunciating each word distinctly. Señor Hill—or Derrick, as he was more commonly known—screwed up his face. He looked around at his classmates, seemingly to confirm whether or not he’d heard his teacher correctly. They were all smiles. "La pluma besa el lapiz," Billingsley repeated.

Derrick quickly touched the pen to the pencil and made a soft smacking sound with his lips.

"No, no, no," Billingsley said. "Un besomuy sexy."

Derrick shook his head in disbelief, then again pantomimed the pen kissing the pencil—this time with a louder smooch of his own to accompany it.

"Muchas gracias, Señor Hill," his teacher said, then turned to the class. "And that’s the only sex scene you’ll ever see here in la clase de español."

Teacher Toni Billingsley.

A class period with Toni Billingsley is a blur of activity. ‘I think the learning experience has to be fun for both the teacher and the student," she says.
—Photograph by Kevin Horan



Clever puns, outright slapstick, sly references to black popular culture—they were all part of the program for the 27-year-old Billingsley, one of six teachers that I, a former teacher myself, had been observing for a book I was researching, about minority educators trying to make a difference in urban classrooms. While fun may be overrated as a condition for children’s learning, in Billingsley’s classroom it was an indispensable ingredient. "I think the learning experience has to be fun for both the teacher and the student," she told me. "If I’m bored, I’m not going to be teaching my best. If the students are bored, I’ll get frustrated, and I won’t be teaching my best then, either. So if I see the class is going the wrong way, I’ll crack a joke or something....Most of the time, we have fun."

The entire class period was a blur of activity, the tall and rangy Billingsley a whirling dervish in sweatshirt, jeans, and tennis shoes at the center of it all. "I’m the star," she told the class at one point. "Look at me." She was kidding, but it was hard not to focus on her. She was all over the place: pacing back and forth, jumping around, leading exercises, gesturing, teasing, making faces and sound effects, her voice rising and falling. The only thing that amazed me more than her stamina was the realization that, as soon as these kids left, another group would come in, and it would be show time all over again.


In 1996, with six years of classroom experience in Chicago public schools under my belt, I began working as an instructor at the Golden Apple Scholars of Illinois Summer Institute, part of a scholarship initiative that prepares undergraduate pre-service teachers from across the state to teach in what the program terms "schools of need." I noticed early on that many of the minority participants, especially those who’d grown up in urban areas, approached teaching with the belief that issues of equity and justice should be central to their work. They’d seen firsthand that public schools were failing many of the kids in their neighborhoods, yet they believed that with the collective efforts of young people such as themselves, schools could become engines of positive social change. Many hoped to teach in communities like the ones in which they were raised and felt committed to working with students with whom they shared racial or cultural backgrounds. Inspired by the determination of these undergrads, I decided in 2001 to seek out young educators—some not associated with the institute—already struggling to "teach for change" in Chicago schools and attempt to tell their stories.

Billingsley attended Chicago public schools from kindergarten through 12th grade, and she was raised for several years on the same South Side block where she and her 2-year-old daughter, Corey, were living. As a young girl, she’d been labeled "the smart one" by family members—her older sister was "the pretty one"—and she came to view her time in the classroom as a respite from some of the hardships she faced outside it.

"When I was a kid, my biggest struggle was my home life," she told me. "It wasn’t school. I had no problem with school. Clothing, bus fare—those were my main issues."

During Billingsley’s youth, her mother spent three and a half years in jail and continually battled drug addictions after being released. Her father, too, was an addict. Neither parent was a consistent presence. "On and off, I saw them," Billingsley said, "but I pretty much raised myself. My mom would come in and out of my life, and I would move around a lot, here and there."

Eventually, she found a semipermanent home with her grandfather, a man who became a constant source of strength and support. He reinforced the importance of education and taught even more important lessons, Billingsley told me, by the way he lived his life. "See, he was not my mother’s biological father," she said. "But he treated her as his own child. And never did I feel that he wasn’t my grandfather. He didn’t treat his biological grandchildren any different than he treated me....I learned from him a spirit of caring and giving and kindness, regardless of whether you’re family or not. You treat people kindly. You do good unto people. And good will come unto you."


Billingsley teaches at the Academy of Communications and Technology Charter School, in the West Garfield Park section of Chicago. At the end of the year, each student hands in a COW, or collection of work, a portfolio that’s used to assess performance. During a Spanish II lesson one morning, Billingsley’s students were revising COW assignments, and the teacher was sitting with Shalisa, a chubby girl in a camouflage shirt, talking over an essay she’d written.

"They was unhappy with the way things was going," Shalisa said. A butterfly-shaped hair clip was clamped to the collar of her shirt.

"What things?" Billingsley asked.

"Like the way the system was."

"What system?"

"The caste system."

The class had been studying New Spain (the name used between the 16th and 19th centuries for what is now Mexico), comparing and contrasting the race-based caste system there with the racial and economic stratification in contemporary U.S. society.

"And why did that make them unhappy?" Billingsley asked.

"’Cause they wasn’t being treated right. The darker you was, the worse off you was. The Indians, they got it bad. And the blacks got it worst—just like now."

Helping her students make connections, Billingsley believed, was a vital part of her work as a teacher. After all, she’d seen firsthand how powerful such learning can be. As a young girl, she’d grown up breathing in the homophobic air that swirled around her: An aunt who helped care for her insisted that homosexuals were hell-bound sinners, and most of her family and friends thought the same. Television and movies amplified the message, and by the time Billingsley went to Illinois State University, where she double-majored in Spanish and psychology while getting certified to teach, she thought her mind was made up on the issue.

I noticed early on that minority teachers approached teaching with the belief that issues of equity and justice should be central to their work.

When one of her college professors offered extra credit to those who attended a meeting of the gay and lesbian alliance on campus, Billingsley balked, thinking she’d be labeled as gay herself. "But I ended up going," she told me outside of class, "and, at the time, they were talking about whether gays should be allowed in the military. And as I listened, I realized that a lot of the reasons people wanted to keep homosexuals out of the military were the same reasons they used to keep African Americans out of the military—and they’re completely unfounded! So I made a connection. And just by making that connection, of me and them being discriminated against for some of the same shit, something just clicked, and I was like, ‘That’s not right.’"

Back in her Spanish II class, Billingsley looked up at the clock.

"One more minute on the computers," she called out to a group that had been working for nearly 30 minutes. "And then you four need to let other people on. If you’re not finished, you can come back after school. I’ll be here ’til 4:30." She turned back to Shalisa and pointed to the second paragraph of her paper. "OK, one thing you need to work on here is writing more about why things were the way they were. Not just what happened, but why."

Watching Billingsley now—low- key, subtle, patiently helping students think about their work—she almost seemed like a different person from the show-stopper I’d marveled at in Spanish I. But that only served to confirm what I’d suspected already: that the jokes, the grandstanding, the look-at-me posturing—they weren’t so much about ego as they were deliberate interventions she thought would help kids learn. When they were appropriate, Billingsley used them—and she had a ball doing so. But just like any good teacher, she had other tools in her kit.

Billingsley was in her fifth year in the classroom. She’d spent the first two of those years at William Rainey Harper, a mostly black high school on the city’s South Side, before being lured to ACT by two former Harper teachers, Sarah Howard and Michelle Smith, who were the fledgling charter school’s co-directors. They hadn’t had to give Billingsley the hard sell to convince her to come. Harper had been put on probation by Chicago Public Schools’ board of education because of low test scores and then been reconstituted—a polite way of saying it had been taken over—which, Billingsley said, had created an atmosphere that was both oppressive and depressing. Teachers would spend hours in meetings with administrators and board officials talking about changes that needed to be instituted, only to watch the reforms fall by the wayside a short time later.

By the middle of her second year, the pressure was becoming unbearable. Billingsley was feeling run-down, even physically ill, and she knew she had to make a change. "When Michelle called me, I didn’t care what the school sounded like—I was like, ‘OK.’ But when I came in, I liked what I saw. I liked that you could create your own curriculum. I liked that nobody was breathing down my back saying, ‘You must do this in this way.’"

By most demographic and statistical measures, the student populations at Harper and ACT were not much different. At both schools, the student body was roughly 97 percent African American, more than 90 percent qualified as low income, and average scores on standardized tests were well below state averages. One important difference, however, was size: Whereas Harper had nearly 1,500 students, ACT had just 270 in grades 6-12.

ACT’s smaller size, Billingsley said, made for a more respectful, reciprocal relationship between teachers and administrators. "At Harper, I had to make an appointment to see the principal," she remembered. "Here, I can just walk into Sarah and Michelle’s office anytime. When they come into my classroom, I love it. They’re not intrusive, and it’s not an evaluation—they just come in to see how things are going. They’re very supportive, and that’s important for a teacher."


No matter how flexible the environment, however, some harsh facts about urban school life simply can’t be avoided. "Race is a big issue for these students," Billingsley told me one afternoon, following ACT’s weekly faculty meeting. "And it affects their attitudes towards new teachers when they come in."

While numerous neighborhoods in Chicago remain highly segregated, school is the one place where many poor African American and Latino kids have day-to-day contact with white people. According to board of education figures, nearly half of the teachers in Chicago’s schools in 2001-02 were white, even though 87 percent of the system’s students were black or Latino. At ACT, the faculty was evenly divided between blacks and whites. "I think the fact that I’m an African American female helps me relate to my African American students," Billingsley admitted. "I don’t know if it’s respect or what, but I think it makes it a little easier. I’ve seen some teachers who have had some wonderful lesson plans, who would be outstanding teachers, but one of the things that hurt them in the classroom was that they were white."

Tawanna (Toni) Billingsley.

‘I think the fact that I'm an African American female helps me relate to my African American students. I don't know if it's respect or what, but I think it makes it a little easier,’ says Toni Billingsley.
—Photograph by Kevin Horan



The problem wasn’t simply a difference in skin color but rather a clash of expectations. "One guy had a lot of liberal ideas that the kids were not used to," Billingsley explained. "Same thing with this other female teacher. She was a wonderful teacher, but she came in and was all about the students making decisions about the curriculum, and they could not understand that. They saw her as a pushover. In their minds, they’re thinking, ‘You’re the teacher. You’re supposed to come in here and say: We’re gonna do this, this, this, this, and this.’ You know, with an iron fist."

The teachers had apparently expected to be viewed as authority figures by virtue of their position. Their students, on the other hand, had expected them to earn their authority by showing they knew how to exercise it. It was a distinction many beginning white teachers in urban schools failed to fully grasp. I certainly hadn’t figured it out during my first few years.

But, according to Billingsley, a number of white teachers at ACT had built strong, mutually respectful relationships with their students. I asked her why they were able to succeed where others failed. "Because they hang in there," she answered. "From day one, you can tell that they care about the students, and they stick in there. See, with these other teachers, after a year, they left. And to the kids, it’s like, ‘Oh, you’re another white person who’s abandoning us. You’re trying to save us, you think that it can’t be done, and then you leave us. You’re not willing to stick with us.’"

While Billingsley thought it was important—crucial, even—for African American kids to have good black teachers, especially black men, in their lives, she believed having teachers from other racial and cultural backgrounds was necessary, as well. "How else are we going to learn different viewpoints if we don’t learn from somebody else’s perspective?" she wondered aloud. "I think it’s a good thing for African American students to have African American teachers—but not only African American teachers. It’s a good thing for Latino students to have Latino teachers—but not only Latino teachers. You bring something different into the classroom as a teacher than I bring into the classroom. Black kids need a teacher who cares, and if that teacher happens to be black, fine. But you can learn from whoever teaches you."

Nevertheless, Billingsley recognized the value of being able to connect on a personal level to her students. As a young girl, she’d struggled against many of the same obstacles they were facing, and she’d seen up-close how an alienating school experience could have devastating consequences.

"Too many of my friends didn’t have a good experience with school, and so they didn’t finish," she told me. "I don’t know if their teachers related to them or not, but I can honestly say that most of my teachers didn’t relate to me. Not many made an effort to get to know me. So I want my students to have a good experience with school. I don’t necessarily want to be the students’ friend, but I do want them to know that there’s somebody outside of their family who cares about them, somebody who’s been through some of what they’re going through. I want them to know that they have somebody they can talk to."


JoJo walked into the room singing: "We got the chicken and the corn bread...."

Book club day had arrived in Billingsley’s reading class, and the accompanying banquet looked impressive. On four pushed-together tables in the center of her room were three plates piled high with fried chicken, two large bowls of macaroni and cheese, a pan of corn bread, a homemade lemon cake, two dozen Krispy Kreme doughnuts (my contribution), a bowl of popcorn, several bags of chips, and a couple of two-liter bottles of pop. There was even a bag of Flamin’ Hot Chee-tos that had apparently slipped through Billingsley’s checkpoint.

The problem wasn’t simply a difference in skin color but rather a clash of expectations.

"Next time we do this, I don’t want to see any half-filled-in sheets," she told the class as she went around to see who had completed the assignment that was supposed to be their admission ticket to the feast. "I’m going to let a couple people slide today, but next time, if you’re not ready with your homework, you can’t participate. The whole point of coming up with questions and passages from the reading ahead of time is so we can be ready to have a good discussion."

"I’m ready, Ms. B," said Nathaniel, eyeing the chicken. "I just didn’t write everything down."

Billingsley wasn’t having it. "What if I said I was ready for us to eat, I just didn’t bring any food? We need more than food on the table to do this—we need food for thought, too. Remember that next time."

She had chosen Lynne Ewing’s young adult novel Drive-By to read with her class for three reasons: It was a well- crafted narrative, the vocabulary was simple enough that her students wouldn’t get frustrated reading it on their own, and it addressed issues she knew concerned them. The story centers around Tito, a 12-year-old who is pressured to join a gang after his older brother, Jimmy, is killed over stolen drug money.

The lure of "quick dollars," according to Billingsley, was one of the most critical issues facing the kids she taught. "They see kids their age who aren’t even in school making big money," she explained. "So they’re thinking, ‘You’re telling me to stick with this school thing, which means I have to not only finish grammar school and high school, but also possibly college if I want a career. That’s a long way off. And here my 7th grade friend is selling drugs and he has all this money in his pocket, and next year he’s going to buy a car.’ So when they see that, they’re like—‘What is all this for? My family is struggling, we can’t pay the rent. I need the money now.’"

As important as Billingsley thought it was to make space for her students’ lives and experiences in her teaching, she acknowledged that it could be a tricky balancing act. "You have this curriculum that, in your mind, you have to teach," she told me. "Even if it’s not set by the administrators. You think, ‘I have to get through this because I want my students to know this content.’ But then the kids will come in talking about being harassed by the police or something like that, and sometimes you just have to put your lesson aside. I don’t have to teach these vocabulary words today if the kids need to talk about that. But it’s hard sometimes as a teacher just to say, ‘Wow, this is a teachable moment—I should go with it.’ I know I’ve missed a few."

Once the book talk started, it didn’t flow as smoothly as Billingsley had hoped. Kids had to stop and wipe their hands every time they went from handling greasy chicken to turning pages, and many of the students’ questions were of the factual—"What’s a crowbar?"—rather than the interpretive variety that make for substantive discussion. A few kids couldn’t add much to the discussion because they hadn’t read the book. Still, it was quite a scene: 15 young people sitting around a table, enjoying each other’s company, sharing homemade cake and Flamin’ Hots, and talking seriously about literature. Oprah would have been impressed.

"So when the guy asked Tito, ‘How’s Jimmy’s business?’ he musta been thinkin’ that Jimmy was involved with the gang," Shalisa offered tentatively.

"Bam! That’s it! Right there!" The words shot out of Billingsley’s mouth. "Now you’re thinking!" Shalisa smiled ear to ear. "OK, how about this passage right here," the teacher continued. "On page 40. What did Tito mean when he said, ‘Jimmy always said he wanted to hear life sing’?"

Students flipped to the spot and scanned the paragraph. "He sayin’ he wanted to make life happy and good," JoJo said. All that was left on his plate were three naked chicken bones.

"Yeah," agreed Shontay. "He wanted to enjoy hisself, to be able to do what he dreamed about doing."

The discussion about Drive-By, coupled with the book club feast, struck a delicate balance that Billingsley constantly tried to maintain in her teaching. On the one hand, she believed in paying unblinking attention to the tough issues that affected her students’ lives and in finding ways to bridge the divide between life inside and outside of school. At the same time, she believed in making her classroom a sort of refuge, a place where happiness and goodness and even fun were plentiful, where students felt significant and valued.

Billingsley knew there were battles for her students to fight out in the world, but there was also beauty to behold. Teaching them to keep their eyes open to injustices and hard realities was important. So, too, was giving them opportunities to hear life sing.


Vol. 15, Issue 6, Pages 29-32

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