Watters is the product of a Quaker education. Born in Philadelphia, he attended William Penn Charter School, the oldest Quaker school in the world. The school emphasizes Quaker values — empathy for others and an appreciation for people from diverse racial, socioeconomic and religious backgrounds. Watters’ father and mother, Stephen and Anne, clearly believed in the school’s mission: They served as director of the middle school and director of lower school admissions, respectively.
When Watters was in high school, the family moved to Long Island, New York, where his father got a job as headmaster at The Green Vale School, an exclusive private school that runs through eighth grade, and his mother got a job as director of admissions. The Watters family lived on campus, but Watters was too old for Green Vale, so his parents sent him to nearby Friends Academy, another prestigious Quaker school attended by many Green Vale graduates.
Even before Watters’ first day at the school, there were signs he would follow a different path.
As part of the application process, Watters visited for something of a tryout, one of Watters’ former classmates recalled. “It was a school that a lot of people got rejected from,” said the classmate. “You kind of understood that if you were there for the day, you had to present yourself a certain way.”
But when class began on the day of his tryout, the gregarious Watters suddenly put his head down on his desk, the classmate said. It was a small class and a small room, and he was right in front of the teacher. But he didn’t appear to care, and it didn’t matter either. He got in.
“Obviously as the headmaster of Green Vale’s son, he was never going to be rejected,” said the classmate.
Watters repeated his junior year during his first year at Friends Academy, which Fox News explained was because of his family’s move from Philadelphia to Long Island. Once there, he immediately made his presence felt. He liked to debate the best way to wear the collar of a polo shirt, his friend Michael Shlofmitz said over email. Others said he would joke about his “hippie” parents, and people described him as friendly and charismatic. He played football and lacrosse. Parents generally liked him.
“He was surprisingly popular,” a second former classmate said.
But Watters was far from a star student, and he could occasionally display a shamelessness his peers found jarring. At one of his friend’s parties, Watters was told there was only one rule: Don’t go into Dad’s bedroom. He did anyway, and stuck chewing gum on the wall and left a burned hole in the carpet, according to two people who were there.
When the father found out, he chased Watters out of the house. “I would have killed him if I had caught him, he was so disrespectful,” the father said. (Watters denied the incident ever took place.)
Watters was often dismissive of authority figures, teachers included, multiple classmates said. “He wasn’t very troubled by shame,” the first high school classmate said.
“It was instantly recognizable, the sort of entitlement, the flippancy, the sort of ego-driven smile,” a third high school classmate said.
Watters’ time at Friends Academy was cut short his senior year after he and a friend got in trouble for leaving campus during school hours. But the school did not formally suspend or expel Watters. Instead, it allowed him to spend his final semester interning at a publishing company while still receiving his diploma on time.
Classmates wondered whether Watters’ father’s influence at The Green Vale School, which fed many students into Friends Academy each year, helped him and his friend avoid harsher punishment. “With his father being in that position of power, I don’t know if he ever had to deal with consequence,” the second classmate said.
The situation was part of a familiar pattern for Watters. “He was just one of those people,” said the third classmate, “that just sort of sailed through life.”
