I come from a family that’s still impressed by long distance travel by air. It’s not so much being in a foreign place but what flying says about your bank account. The Jefferson’s marked movin’ on up by the smells no longer stinking up their new kitchen but, because I’m an immigrant, flying became an early measure of upward mobility. I still recall the two outfits mom had specially made for me to travel by air: one to visit my aunt and grandmother in New York City and years later, another for the one-way trip. I was 9 then. I still equate flying with the cost for a single mom from a country village in Barbados to special order two tailor-made outfits.

I’ve been thinking about flying lately because Monday night PBS premiered "American Promise," the documentary about two black boys’ journey through my alma mater, The Dalton School. Popularly known for educating Claire Danes and Anderson Cooper (but really for attracting wealth that doesn’t court the camera), Dalton is a $40,000-a-year predominantly white and Jewish private school on Manhattan’s Upper East Side. The film joins other real and fictional accounts, including "The Prep School Negro," "Finding Forrester" and "School Ties," in depicting outsiders attending school with the children of the one percent. Most significantly, it opens up what has been an insular conversation around racial integration in one of the country’s few Ivy League feeders.

When I started in the seventh grade in 1989, I was fresh off three years at a public school that had been ranked as one of the worst in Queens the year before. Mom knew things were bad before the department of education, however. For at least a year, I’d been heading into different Manhattan buildings to take tests, including one for my IQ. I did well and chose Dalton because, compared to similar schools I’d visited, it allowed kids to "be." They lounged on floors. Their art covered walls and lockers. I received a significant scholarship, but paying for Dalton was still a hardship for my mom. I carried that burden daily until I graduated in 1995 and, for many years after.

Early that fall I tried making friends. I’d scooted up to a few white girls lounging on the floor and one of them was talking about flying to Paris. But here’s the thing: it was only for the weekend. She’d fly back in time for classes on Monday. I was used to kids, especially kids with only a dollar more, bragging. This was something else. Another working-class alum Erica Terry-Derryck explains our social education best. On the phone from the Bay Area, where she now lives with her family, she recently told me: "I describe Dalton to people as somebody pulling back a curtain."

What fascinates me about "American Promise" though is how the parents–particularly the filmmakers–expected, with no irony, that a majority white and super privileged space not just educate but also nurture and support their black children. That’s different. Why would a black person expect that level of care and love from a historically white, elite institution? It got me thinking about whether my crew from the late 80s and early 90s and our parents expected the same. And if they didn’t, is "American Promise" demonstrating a kind of progress with this demand or exhibiting a post-racial brand of naivete? I chatted with a few alums to try to figure it out.

* * *

"In our own way we were all the Ruby Bridges of independent schools," Christine Johns-Harris says on the phone from her home in Atlanta. Christine, an educator-turned-baker, was a year ahead of me. And while she agrees our experience doesn’t compare to a 6-year-old desegregating a white public school in 1960s New Orleans, our numbers, unique composition and time in which we entered Dalton help to make her point.

I didn’t realize it at the time, but I belong to the first critical mass of students of color to integrate elite day and boarding schools. Programs like Prep for Prep, The Oliver Scholars and A Better Chance, which creamed smart kids from public elementary and junior high schools, established this beachhead. At Dalton, that meant a class of 100 kids that had seen one or two students of color suddenly added 12. That number seems small but it was big enough for the black, Puerto Rican and Dominican kids to congregate. It was big enough to take over a cafeteria table. It was big enough to create an impression and shift conversations.

While I entered on my own, most kids of color entered Dalton through a program like Prep for Prep. That lifelong association meant they received extra academic help and mentoring and networking opportunities before, during and after Dalton. Most, though certainly not all of us, were on varying levels of scholarship. Among my crew there was a girl whose mom worked in the cafeteria and her dad was a janitor.

At the time New York City, more than it is today, was a racially segregated and angry city. A couple of weeks before I started seventh grade, a mob of young white men killed an unarmed black man. All that year, the media raged over five black and Latino boys who’d allegedly beaten and raped a white female jogger up the street in Central Park. Crown Heights, a low-point in the city’s black-Jewish relations, rioted a couple of weeks before I entered the 9th grade. I remember panic among some white kids in the hallways when Los Angeles exploded the spring of my 9th grade year. Dalton was and still is a cosseted space. But it did not exist in a vacuum–and to its credit, the school provided space for political expression that I can’t imagine finding in a public school or another prep school.

"Oh it was definitely a political and pro-black time," says class of ’94 grad Jerry Wallace, rattling off music and fashion like Public Enemy, X Clan, Brand Nubian and, laughing, he adds, Cross Colours clothing.

I didn’t come from a political family like many of my peers. In fact my West Indian mother complained during high school that I was, "too in to this black ‘ting." Looking back though, I’d begun my education in a country with a 99 percent literacy rate and where competitive education was the norm. I grew up being ranked, and in a community that paid attention to which children came first, second or third that year. That skin color influenced or determined achievement or lack thereof, I learned in the United States. What sparked my consciousness was knowing an alternative to the racial and class segregation that I was now living and, the dominant negative narratives about black people I now heard. Dalton, by collecting what struck me then as an admirable group of students of color, nurtured my nascent politics.

So many of my black classmates possessed a strength and confidence that I associated with their home lives. I don’t know if the other large co-ed schools like Trinity or Horace Mann gathered a similar fist but at Dalton, my classmates’ parents and family members were heroes in the National Black Arts movement headquartered in Harlem, South African exiles and anti-apartheid organizers, members of the Nation of Islam, and civil and human rights attorneys. I remember for a period, some of the older high school boys playing a game called, "bad habit." Every time someone said "nigga" they got smacked. Hard.

"We were all kente and mud clothed up and walking through Dalton," Christine says. "They weren’t prepared for intelligent kids who were not willing to assimilate. I think that was the difference with us."

All of the above bred within us, a certain defiance. Being large enough to congregate in what was often an isolating environment meant parenting and supporting each other. Getting to and from Dalton meant traveling up to three hours daily through our racially tense city, an education in ambassadorship and code-switching on its own. And unlike me, my friends had heard or learned about Biko, X, Garvey, Mandela, or Lumumba before their 10th birthdays. Certainly that defiance manifested along a spectrum of behavior. Some of the older kids regularly staged walkouts in protest of some offending thing at the school, in the world or around the country. I wrote–enough about racial integration in one year on our school intranet to fill a book.

Of the alums I’ve interviewed, I’m learning that some of their parents overtly managed their expectations. Assimilating into Dalton was not the goal. And, for some, neither was integration.

One day in the seventh grade, class of ’91 grad, Erica Terry-Derryck says she came home and pitched a fit. Everyone at school had the $60 canvas bookbag from Chocolate Soup on Madison and 75th and she wanted it too.

"Mom was like, you’re not everyone; you live in the Northeast Bronx," Erica says. The argument and the message are still clear today. She remembers her mom saying, "I’m sending you to school there so that you know how to excel and deal with white people who run shit. I don’t care if anyone likes you, or if you like it. That’s not why I’m sacrificing. The quicker you wrap your mind around that the better it’ll be."

"I still wanted that bookbag," Erica says. But, "that conversation also gave me a different orientation about what I was supposed to do there."

"Our parents said–and I know this–you’re going to get what you can get and leave," Christine says. "I think the kids who came [later], I think their parents were saying, ‘This is the best, this is what you aspire to.’ And I don’t think our parents ever said, ‘Aspire to be one of them.’"

* * *

Bunmi Samuel was one of two black boys who entered the seventh grade with me. Flipping through our yearbook the other day, a few quotes from his page held me captive: "I stand before you as a proud Black man…," "My hair would be…a statement of self-affirmation," and James Baldwin’s, "To be a Negro in this country and to be relatively conscious is to be in rage almost all the time."

"I was in defense mode, then" he tells me on the phone from Philadelphia. I knew what he meant before he explained.

I first learned the default assault when I was 12, from one of my Mom’s bosses. She, along with other Caribbean women, worked in the back office of an international bank. Her boss couldn’t hide surprise and a couple of other feelings when she introduced us. "How did you get into Dalton?" was what he really wanted to know but couldn’t ask.

Over time, I got to know that often intimated rarely verbalized question well. It wasn’t always present, but for self-protection it was best to expect it. Even adult supporters I found–people who otherwise were trustworthy–justified inquiries into the intellect of black people with debate.

To appreciate the impact of these assaults, understand that Dalton is a cathedral for the mind. PhD’s teach there because they find it intellectually stimulating. It’s not enough for students to be smart; they must love learning.

Even if Dalton students are too young to articulate it, exercising the mind is a defining element of our identities. Challenging or indulging questions about my intellect, then, undermined me at a time when I was forming my identity and figuring out where I stood in the world. I find it difficult to believe that white students then or now report a similar and sustained assault on their emotional and intellectual development. Silence, while these debates over black intellect rage and stereotypes fly, is no remedy. It’s child abandonment.

"White privilege was the invisible smoke in the room," says Bunmi, who adds that he thinks about Dalton in his work daily designing curricula and improving systems in Philadelphia public and charter schools.

"As a kid you can’t even articulate it and you’re trying to figure out how to clearly speak about what you see."

Jerry Wallace, like Bunmi, was a sports star. "A lot of people were cool," he says more than once during our conversation, "but you got the sense some people were like, What are they doing here?"

His first week at Dalton in the ninth grade, he says, a white girl came up to him after science class and introduced herself with the following question: "What sports do you play?"

"Why?" he recalls asking, "Are you a cheerleader?"

Jerry, known for a quick tongue, explains his reply this way: "If you’re going to assume one thing by looking at me, I’m going to assume one thing also."

Incidents like the above, left unchecked and repeated over time, corrode trust and faith not only in adults but in institutions, too. Which brings me to my mother.

* * *

My mom is a quiet and private woman. She had lived in the United States a couple of years before looking to trade up. She saw a school. She saw a good school. I was a child. I was a smart child. The good school would teach her smart child. Her decision-making at the time sprung from a Dick and Jane book–as did my own. Yes, I recall telling Mom when we first visited Dalton for my interview, "There’re a lot of white kids." But it was only an observation. It carried no judgment or expectation of all that lay behind the curtain.

Only over time I realize, now, in this very moment, did I learn to not expect care, protection or grooming from a historically white, elite educational institution. Use it for what I could get and move on, so goes the unspoken mantra of many strivers. But should it be that way? Didn’t I deserve the full measure, too? Looking back at my crew, we were all in our own and sometimes imperfect ways, asking those same questions. I’m grateful to "American Promise" for reminding me of a time when I still asked, of when I was very young and still saw with new eyes. Why would a black parent expect care and love for their whole child from a historically white, elite institution? Why not?