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Jeffrey Epstein Taught at Dalton. His Behavior Was Noticed.

Some students at the esteemed Manhattan prep school recall that Mr. Epstein, now charged with sex trafficking, was willing to violate norms in his encounters with girls.

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In the mid-1970s, students at one of New York’s most esteemed prep schools were surprised to encounter a new teacher who pushed the limits on the school’s strict dress code, wandering the halls in a fur coat, gold chains and an open shirt that exposed his chest.

The teacher, Jeffrey Epstein, would decades later face allegations that he coerced and trafficked teenagers for sex. At the Dalton School on the Upper East Side, some students saw Mr. Epstein as an unusual and unsettling figure, willing to violate the norms in his encounters with girls.

Eight former students who attended the prestigious school during Mr. Epstein’s short tenure there said that his conduct with teenage girls had left an impression that had lingered for decades. One former student recalled him showing up at a party where students were drinking, while most remembered his persistent attention on the girls in hallways and classrooms.

“I can remember thinking at the time, ‘This is wrong,’” said Scott Spizer, who graduated from Dalton in 1976.

None of the female students who spoke to The New York Times in recent days remembered Mr. Epstein making unwanted physical contact with them, and he has not been accused of any crimes related to his time at the school.

But a few students said they had been discomfited by a close relationship he had with one of their female peers, a concern that had escalated so much that one of them had raised the issue then to a school administrator.

Dalton has long been known for its rigorous academics, repeatedly ranking among the nation’s best private schools while drawing the sons and daughters of New York titans of finance, media and art. Among the alumni are the CNN journalist Anderson Cooper, the actress Claire Danes and the comedian Chevy Chase.

Mr. Epstein’s time at Dalton was brief, and an administrator said it ended in a dismissal. While Mr. Epstein later developed a reputation in the world of finance as a man of brilliance — “He was a Brooklyn guy with a motor for a brain,” New York magazine wrote in a 2002 profile — the administrator told The Times that he had dismissed Mr. Epstein for poor performance.

But the accounts offer a window into Mr. Epstein’s early adulthood, before he developed extensive private wealth that allowed him to acquire a $56 million mansion just a mile south of the Dalton School. It was there, prosecutors said this week, that Mr. Epstein and his employees paid “numerous” underage girls to engage in sex acts with him.

Federal prosecutors in New York charged Mr. Epstein, 66, with sex trafficking on Monday. He has pleaded not guilty. His lawyer did not respond to a request for comment.

Officials with the Dalton School also did not respond to requests for comment, but news of the charges has led alumni to reconnect and swap memories of a young teacher who sometimes seemed to defy the expectations of behavior for an authority figure.

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Like much of the rest of the country, the Dalton School in the 1970s was in the midst of a culture war.

The school, which had been a progressive haven for the children of artists and writers, was undergoing a shift under a new headmaster. Donald Barr, the father of Attorney General William Barr, came in as a disciplinarian focused on beefing up the academics of the school, and on enforcing a strict code of conduct.

In a school known for creativity, administrators had prohibited denim jeans and “bizarre and eccentric costumes.” If Mr. Barr caught students using marijuana, he would often send them to therapy as a condition of staying in the school. He himself described his leadership style as “by ukase,” using the Imperial Russian term for an edict from the czar.

Staff members would sometimes turn students away from their morning classes; girls for skirts that were too short, and boys for hair that was too long.

Some students and parents balked at the constraints. Still, the school continued to draw families of fame. Around the years of Mr. Epstein’s tenure, records show the student roster included Prudence Murdoch, the daughter of the media mogul Rupert Murdoch; the fashion designer Jill Stuart; and several future actresses, including Jennifer Grey, Tracy Pollan and Maggie Wheeler.

While Mr. Barr was strict on the school culture, he made it a point to hire teachers from unconventional backgrounds, recalled Susan Semel, a social studies teacher at Dalton from the 1960s to 1980s who later wrote a book on the history of the school.

“Barr didn’t care about credentials as long as you were interesting and knew your stuff,” Ms. Semel said.

In February 1974, Mr. Barr had announced that he was resigning as headmaster, protesting the meddling by the board of trustees, but that he would stay on until the end of the school year. It is unclear whether Mr. Barr hired Mr. Epstein during that time.

Mr. Epstein, from Brooklyn, was just 21 when he joined the faculty at Dalton, arriving without a college degree. The school’s student newspaper reported in September 1974 that he was starting that year as a math and physics teacher.

The next year, he participated in a school musical for parents and faculty, and he appeared in later editions of the paper as the coach of the Dalton Tigers math team until the beginning of 1976.

The school had new leadership under Gardner Dunnan, who tentatively explored a rollback of some of its strict rules. Mr. Dunnan announced in early 1975 a policy that would allow denim inside the building, although students were still told to be neat and clean.

In the years since, however, Mr. Dunnan has faced allegations of his own inappropriate conduct. A former Dalton student said in a lawsuit that she had been invited to live with Mr. Dunnan at age 14, and had suffered repeated sexual assaults under his care. Mr. Dunnan denied the allegations. The lawsuit was dropped, but the woman’s lawyer, Mariann Meier Wang, said she intended to refile it.

At Dalton, Mr. Epstein was known as a charismatic, young teacher who at times acted more like a friend than an authority figure to students.

The urban school inside a brick building did not have outdoor spaces to congregate, so students gathered in halls and in rooms that spanned the building’s many stories. That included lab rooms dedicated to various subjects, providing a more informal and intimate setting for students to get help outside of class from their teachers.

It was in one of these lab rooms that Leslie Kitziger, who graduated from Dalton in 1978, first met Mr. Epstein.

Ms. Kitziger remembered him as a flamboyant dresser and lively jokester. “He was goofy and like a kid himself,” she recalled.

Ms. Kitziger said she became close to Mr. Epstein at a time when she was struggling at home with her parents’ divorce. She confided in him, and remembered him as caring and attentive.

“He listened,” Ms. Kitziger recalled. “I was a 14-year-old and he helped me through a time when there wasn’t anybody else to talk to. I felt like he really cared that I was having a rough go.”

She stressed that Mr. Epstein was always professional with her.

But other students, including Millicent Young, a graduate of the school’s 1976 class, saw things differently. Ms. Young never had Mr. Epstein as a teacher, but the school was small enough that she would spend time around him. She recalled observing Mr. Epstein flirting with the girls at the school, which drew her attention because it was so different from how other teachers behaved.

“There was a real clarity of the inappropriateness of the behavior — that this isn’t how adult male teachers conduct themselves,” Ms. Young said.

Mr. Spizer, the fellow student who graduated the same year, said he had a clear recollection of disliking Mr. Epstein because he was spending so much time with girls in the school.

Some other students spoke on condition of anonymity, fearing retribution from Mr. Epstein. One recalled that he had made efforts to spend time with her outside the school, and she remembered raising concerns about Mr. Epstein’s conduct with another student to Mr. Dunnan. An attorney for Mr. Dunnan said the former headmaster had not been aware of any concerns about Mr. Epstein’s conduct at the school.

Another student, who also requested anonymity, fearing reprisals from Mr. Epstein, recalled seeing Mr. Epstein at a high school party in an apartment on the Upper East Side where students were drinking and socializing. Mr. Epstein was the only teacher there, which raised eyebrows among the students.

“It was weird,” said another former student, Paul Grossman, a 1978 graduate who did not attend the party but remembered hearing about it. “Everyone talked about it,” he said.

Peter Thomas Roth, who graduated from Dalton in 1975 and later founded a cosmetics and skin care company with his name, said Mr. Epstein was such a “brilliant” teacher that his father later hired him to tutor Mr. Roth in statistics.

Mr. Roth said he never heard of any rumors about misconduct at the school.

“He was like your friend, you know?” Mr. Roth said.

But Peter Branch, who was an interim headmaster after Mr. Barr and later the head of the high school, was not as fond of Mr. Epstein’s teaching. He said that he did not recall anyone raising concerns to him about Mr. Epstein’s conduct with students, but that he had heard concerns from the faculty about Mr. Epstein’s teaching, and eventually determined that the teacher needed to go.

“Epstein was a young teacher who didn’t come up to snuff,” Mr. Branch said. “So, ultimately, he was asked to leave.”

Mr. Roth, the former student, said he and Mr. Epstein did not stay in close touch. But a couple of years ago, he got an invitation to Mr. Epstein’s home after running into him.

It was the only time he had been invited to Mr. Epstein’s palatial townhouse, he said, and so he went over for an afternoon gathering. Everyone present was in their 40s and 50s, Mr. Roth said, and there was no untoward behavior.

Michael Gold contributed reporting.

A version of this article appears in print on , Section A, Page 16 of the New York edition with the headline: New Teacher in Gold Chains, and Lingering Questions Over Conduct. Order Reprints | Today’s Paper | Subscribe

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