From the June 17, 1949 edition of the Gazette:

Among the many youths graduating from Island high schools this week, there has been one who was slightly bewildered by an honor accorded him. He is Robert Waring, 18, of Oak Bluffs High School, who doesn’t “know why I was picked as class pessimist.” He hasn’t even managed to convince himself that it was entirely an honor.

He is a tall, slim young man with close-cropped black hair and strong arms, and he talks with an occasional broad grin containing a suggestion of embarrassment. Asked why he had been chosen as pessimist, he said, “You just have to ask Harry Dorr, our English teacher. He picked me. I don’t know why. I’m not pessimistic.”

The honor entailed his presenting a talk at the class day exercises in the Oak Bluffs High School gymnasium, whose gray frame exterior Bob pointed out from the front porch of the Waring house just below the high school itself on School street. The exercises were held Tuesday in a crowded auditorium, and he admits that “people laughed at my talk.”

He reports, however, that his remarks did not come easily to him, the pessimist being a role to which he is unaccustomed. But the substance of his talk had a ring of conviction which may have indicated to the casual listener that Mr. Robert Waring would just as soon see the world atomized as continue on in its present sorry way.

“I haven’t the slightest idea why I was chosen as the class pessimist out of such an enormous class (eleven pupils),” his talk began, “when there are so many other candidates. It seems to me I agree with everything that goes on in our class.”

He told the crowd that he had first entered this school six years before, and that at that time “I doubted very much that the class of ‘49, especially myself, would ever see this graduation year.” His fellow students remember him even earlier than that. “Shy Bob went lazily around the room getting acquainted with the rest of the prisoners,” is the way he is described in the class history as deporting himself when a first-grader in 1937.

“Browsing through the gold-paved corridors,” his talk continued, “one sees the future seniors. I see the seventh graders as a group of Dr. Jekylls and Mr. Hydes; at one instant they are sweet little angels and at the blink of an eye they are transformed into many tiny little gremlins gumming up the precise procedure of Oak Bluffs High School.”

Bob had equally uncomplimentary things to say about other of his schoolmates. The sophomores who are studying to be electricians, for instance, were described as “all qualifiers for the executioner’s job at Charleston: they like to give people shocks . . .” The seniors got off easier. “I see the seniors as the master minds and geniuses of the future,” he said. “They will be so clever in solving the world problems, that they will put the whole universe in a state of wild madness.”

At this point in his address, Bob encountered a modified form of censorship. He had naturally had to submit a copy of the proposed address before actually delivering it, and there had been objection to one paragraph as “too sarcastic,” which was expurgated from the talk in its final form. “I don’t understand what the fuss was about,” he said quietly. “I was only trying to stay in character — the character they gave me.”

His conclusion was on a happy note. “In twenty years I would like to see how my classmates fared,” Bob announced. “Half of us will probably be haggard and decrepit, old and broken before our time, and lost in the fog of the world.”

“I don’t really believe that, though” Bob confided, balanced on the wooden railing of his front porch. “I haven’t thought about it much.”

Bob says that he thinks the school is really “pretty good.” He attended its first three grades, and returned for his sixth and seventh years after spending two years off-Island. He was in Boston schools for the eighth through eleventh grades, and came back once again this year to finish his high school education at Oak Bluffs. He likes the Island, but isn’t sure whether or not he’ll spend much more time here. His ambition is to enter the civil service, perhaps as a postal employee.

In a section of the mimeographed class day program, which serves as a sort of year book, he prophesies that the future will probably find him a “nervous wreck,” but he is apparently merely remaining in character as a pessimist.

At one point during the Gazette’s talk with Bob, a girl passed up the road in front of the Waring porch. She was abreast of it when she stopped in her tracks and shouted “Hey, stuck up!” Bob looked at here and smiled. “I spoke to you and you didn’t even speak to me,” she hollered.

“Hi,” he yelled to her, laughing. He seemed both friendly and joyful in his greeting to her, and it was necessary to strain one’s imagination to picture him cast as the pessimist of the year at the Oak Bluffs High School. If it was type-casting, the class of 1949 must be an extraordinarily jovial bunch.

Compiled by Hilary Wall