WHEN Ayinde Alleyne arrived at the Trinity School, an elite independent school on the Upper West Side in Manhattan, he was eager to make new friends. A brainy 14-year-old, he was the son of immigrants from Trinidad and Tobago, a teacher and an auto-body repairman, in the South Bronx. He was soon overwhelmed by the privilege he saw. Talk of fancy vacations and weekends in the Hamptons rankled — “I couldn’t handle that at that stage of my life,” said Mr. Alleyne, now a sophomore at the University of Pennsylvania — and he eventually found comfort in the school’s “minority corner,” where other minority students, of lesser means, hung out.
In 2011, when Mr. Alleyne was preparing to graduate, seniors were buzzing about the $1,300-per-student class trip to the Bahamas.
He recalls feeling stunned when some of his classmates, with whom he had spent the last four years at the school, asked him if he planned to go along.