Ray says his own personality came through loud and clear as early as the fifth grade. His teacher assigned the age-old paper: "What I did last summer."
Ray refused to do the assignment because "I said I didn't do anything," he explained in the same incredulous tone his teacher must have heard 45 years ago. Ray was forced to write the essay, but not the principal, not his parents and later, not college, nor a stint at the CIA, nor even law school, could dampen Ray's desire to do things his way. Thousands of HB alums are thankful.
Ray spent his early childhood in Pleasant Hills, just south of Pittsburgh, where his poor academic performance was a constant cause for concern. "I was bad enough in school as a student that my parents actually thought about sending me away somewhere," he remembers.
Instead, his parents moved the entire family to the upper-middle-class suburb of Mt. Lebanon. "The idea was if the schools were better, maybe I'd be a better student. That was the theory, at least," Ray says.
Unfortunately for Ray's parents, their theory ran smack into reality: Ray's grades didn't change. Ray says it wasn't so much that he wasn't interested in studying as it was he was interested only in certain topics and not necessarily what his teachers assigned. "Occasionally," he remembers, "I would have a teacher who would let you study what you wanted to and in the way you wanted to. And I obviously would do better in that class."
That pattern continued in 1959 when Ray began his freshman year at Penn state. He majored in arts and letters -- a degree that offered students flexibility in choosing courses and, consequently, his grades improved. Ray also experienced what would be a feature of HB Woodlawn's curriculum by taking the only independent study class offered at Penn State.
Though never a conservative, Ray believes he became more liberal in college and, when he became eligible to vote at age 21, he registered as a Democrat -- "A violation of family history for several generations."
While Ray's world view moved leftward at Penn State, his life changed in other ways, too. One day during his junior year, Ray started arguing campus politics with a woman in the dining hall. Before long, they realized they had something in common. They began dating and the next year, on June 9, 1963, the same day they graduated, Ray and Sara Peterson were married. They've been married ever since.
After graduation, Ray went to work for the CIA in Langley, Virginia. He explains that in the early '60s, the Agency was not such an unlikely choice for a liberal-minded young man as some might think today. Many liberals, he says, believed the CIA was fighting the good fight around the world.
Ray wrote reports and did research while being trained as a spy. It didn't take long before Ray's rosy view of the CIA turned darker.
He remembers that after the Bay of Pigs crisis in 1961, 'the CIA kept on doing infiltrations ... In 1964, I know I was working with Cubans who were still going in ... All of that was kind of unknown .. even in Congress."
His ultimate disillusionment came in 1965 when President Johnson sent the marines to the Dominican Republic to put down an uprising viewed as potentially communist. When critics questioned this move, the President sought intelligence information from the CIA that he use to justify the action.
Ray was assigned to investigate one of the apparent leaders of the communist takeover and began pouring over intelligence reports. He concluded that while the target of his investigation was a leftist and a socialist, he was not a communist or a revolutionary.
"I gave this to my supervisor, kind of pleased with myself for my precision," Ray recalls. "He looked at it and he said 'well, this won't do. We can't say he's not a communist. The president has to tell Congress these are all communists.'" The supervisor rewrote the report and -- although he didn't know it -- the next chapter in Ray's life.
Disheartened with intelligence work, Ray hung around until 1967, when he left to complete a master's degree at American University. He also became certified to teach.
In late 1968, a job opened up at Wakefield High School. Ray began teaching history and social studies.
But he soon found himself constrained by traditional education and, unsure that he had a future in teaching, applied to some local law schools.
Then it happened.
Around Christmas 1970, Ray and his wife were driving in their VW camper to visit his parents. Ray was mulling over his frustrations when he said "what we really need to do is have a completely different kind of school."
His wife pressed him. "Well, what kind of school would you like?"
Ray began naming a few ideas and suddenly realized he was onto something. "I said get out some paper and write this down. And so I dictated this five-page memo."
In six short months, Ray's vision became a reality. To keep his options open, he went to law school part-time, eventually earning a degree from GWU in 1976, but he was having too much fun to look back. Until recently.
As HB has grown older and developed a reputation for top-notch academics, Ray worries that it has become more like the tradition high schools to which it was supposed to be an alternative.
He notes that in the old Woodlawn Program (before it merged with Hoffman Boston in 1978), the English teachers refused to teach AP English because they considered it elitist. "Now we pride ourselves on our AP scores," he says. "We exceed the national average by more than half a point." He also remembers when students laughed at proms and were more interested in politics and theater than getting into Ivy League schools.
Part of the change may be due to the faculty ("we're acting our age," Ray quips) and part may reflect a new generation of students. But in acknowledging a shift toward the conventional, Ray maintains that, at its core, HB is still progressive. "There's still a town meeting, there's still electives, there's still an open campus," he argues. "The structure that gives student control over their own education is still there."
After more than a quarter century, Ray is concerned with leaving a legacy. Although he can retire in two years, he wants to stick around so he can pick replacements for about half the current staff who will be retiring early in the next century.
One can imagine the resume items that might catch Ray's eye: "published poet," "leads spiritual wilderness trips," "Oberlin College grad." On the other hand, he might just be looking for some disenchanted former CIA operatives with law degrees whose parents wouldn't vote Democratic to save their lives.
In either case, his goal will be the same: to ensure that come 2010, HB is still HB, even if there is a prom, students aspire to Harvard, and the principal isn't named Ray Anderson, hard as that may be to believe.