stop, he said. You really should.
The meeting ended. Mike left feeling more disoriented than ever, and the feeling just worsened as the year went on. Most of all, he felt alone going through the biggest culture shock of his life, a shock that was not about race. He’d attended a largely white school at St. Mary’s, so being the rare black at Milton was not a foreign experience. It was the wealth; he’d never been around or seen such wealth before. He became acutely self-conscious. Seeing some of his classmates’ mansions left him paralyzed socially. “I was petrified to bring anyone from school to my house. It was just embarrassing, you know. Oh my God, look at the house I live in, look at how these people live.” He dodged conversations on campus when classmates talked about where their fathers went to college—Yale, Princeton, Harvard, and other elite schools. He was embarrassed his aunts and grandmother were maids. He was even embarrassed his mom’s name was Bertha.
Mike could not figure out how to make Milton work. He was a day student when most of the kids boarded on campus. With his commute, team sports, and the piles of homework, he found himself in a hole academically. “I had a lot of D’s and C’s at first.” It wasn’t as if the schoolwork was too difficult for him, he just could not find time to complete it. “The perception was that I wasn’t doing my homework because I couldn’t do it. But I wasn’t doing my homework because, at the time, I was just tired all the time and, I mean, there was a lot of stuff going on in my life.”
Meetings with teachers and advisers did not help—mainly, once again, because Mike let stand their assumption that the work was over his head.
You can’t do this, can you? Mike was asked. It’s really difficult, right?
“I was just like, ‘Yeah, I guess so.’”
By early spring, Mike thought he was making progress. Not playing a sport, he had more time for his schoolwork, and his grades improved. But it was apparently not enough. “My adviser went from ‘You smoke pot, don’t you?’ and ‘You have trouble doing the work, don’t you?’ to ‘You don’t really want to be here, do you?’”
It became a refrain: You’re not happy, are you?
Mike did nothing to rebut the school’s wrongful assessment, a response that was becoming a pattern. The next thing he knew, he would not return to Milton Academy. His mother and oldest sister Cora began working with administrators at Milton to find Mike a new school. In the spring and summer he visited other campuses, such as the Northfield Mount Hermon School in western Massachusetts and the Wooster School in Danbury, Connecticut. Mike was not impressed. “They all looked the same to me,” he said. And both schools meant he’d have to leave home and board. “I didn’t want to be a boarder.”
But what Mike thought did not matter. “My mother told me I was going to Wooster because it was a full scholarship and everything was booked—the whole nine yards,” said Mike. “So it was decided for me.”
In 1981 when Mike went to the Wooster School, he joined a sophomore class that numbered between thirty and forty students. The Episcopalian school, founded in 1926, took pride in its small size and its progressiveness. It became coeducational in 1970. Mike’s class had a few more boys than girls in it, and he was one of a handful of blacks. One of the other black scholarship students—a senior during Mike’s first year—was Tracy Chapman. They had very different interests. Mike’s focus was sports; Tracy was interested in politics, the black feminist poet Nikki Giovanni, and her music. She played at the campus coffeehouse Friday nights, where she sang songs she was working on, including one she titled, “Talkin’ ’bout a Revolution.”
Mike’s mom, dad, and sister drove him down from Boston at the start of school in September. Most of the other kids were already on campus and unpacked. Mike was