The Outsider: Jeffrey Epstein at the Dalton School
Note: I wrote this story for Town & Country, where I am a contributing writer, before Epstein was found dead in his cell at the Metropolitan Correctional Center on August 10th. My editor thought that events had outpaced my reporting, but I think the connection between America’s most famous pedophile and a former all-girls’ prep school bears some scrutiny.
In 1978, Woody Allen was doing an interview with Newsweek’s Jack Kroll when a teenage girl asked him for his autograph. Staring longingly at her afterwards, Allen speculated about what would happen “if my moral sense ever sinks as low as my other senses… It wouldn’t look good for me to hang around the Dalton School with my collar turned up.”
A year later, the director was filming Manhattan at the former all-girl prep school; the character he plays in the movie was having an affair with a 17-year-old Dalton student (played by Mariel Hemingway), and he didn’t have to turn his collar up. Ike, Woody’s 42-year-old alter ego, complains to his friends, “I’m dating a girl who does homework.” Diane Keaton’s character wisecracks, “Somewhere Nabokov is smiling.”
Betsy Gitelle was senior at Dalton that year, and few on campus were shocked by Manhattan’s spring-fall romance: She recalls at least two students who were dating teachers when she graduated, and no one raised an eyebrow. “I don’t know if I thought it was weird at the time,” says Gitelle. “It’s really hard to not superimpose today’s thinking on what the experience was really like as a kid at Dalton in the ’70s. You were in a milieu that was about power and wealth and people taking what they wanted. And it was just the way the world was there.”
She also remembers Jeff Epstein, her eighth-grade algebra teacher, who taught there from 1974 to 1976. He wore bell-bottoms, platform shoes, a big chunky belt and a striped T-shirt. “I remember that he always used to stand in front of the desk, sort of leaning against the desk, half-standing, with his arms crossed, and talking to us kind of in a pose. He was famous for was being an easy ‘A.’ And he definitely wanted to be one of us; he wanted to be in on everything, like who was into a clique … He wanted to know too much about us.”
In the wake of Epstein’s arrest in July (he was just back from Paris when he was pulled off his private jet at Teterboro Airport and charged with running a sex-trafficking enterprise between 2002 and 2005), Dalton alumni have been talking to each other about their recollections of the erstwhile math teacher. A few say he showed interest in several vulnerable young Dalton girls and tried to tell the administration, though there is no evidence of that. Epstein began teaching there when he was just 20, and his interest in young girls may have been budding then.
“I did not get any kind of sexual vibe from Jeff Epstein,” says Gitelle. “He was definitely checking us out and approving of us. I mean, how adorable were we? But all the men around us were always ogling us and approving of us. It was just how we lived. So he wasn’t especially close or creepy or pedophiley or anything. He was just this camp counselor type of guy that happened to be our math teacher for a year.”
Some pedophiles gravitate towards jobs like camp counselor, or even teacher; to paraphrase Willie Sutton’s line about why he robbed banks, it’s where the kids are. But Dr. Anna Salter, who has examined countless sex offenders in her work, says Epstein is more accurately labeled a hebephile, someone who is attracted to 11 to 14 year olds. A detective who investigated Epstein said he lost interest in girls when their braces came off. “That’s the kind of statement that we associate with hebephiles,” says Salter, who has written extensively about sexual predators and pedophiles, and emphasizes that she has not examined Epstein. “Many of them just lose interest when someone becomes fully mature and has an adult body.”
The erstwhile math teacher’s keen interest in the teen and tween scene (the New York Times reported that Epstein attended a student party while he taught there) may have also been a warning sign. “Most of us who leave adolescence are really happy to leave that sort of petty gossip and drama behind,” says Salter.
Why was Epstein at Dalton in the first place? He’d been an outstanding high school student, and graduated two years early. But he had no college degree when he taught at Dalton, though he had briefly attended Cooper Union and NYU. But Dalton had a reputation for unconventional hires. The headmaster at the time was Donald Barr, father of US Attorney General Bill Barr, and a controversial figure in his own right. One parent called him “the Captain Queeg of Dalton School,” prone to high-handed authoritarianism at a campus with a looser academic reputation. He was right wing during the Vietnam War, when much of the staff, and students, were on the other side, and some of his hires may have reflected his bias. Bill Adler, who attended Dalton in the seventies, recalls “an economics teacher who essentially taught the philosophy of Ayn Rand.” And then there was the anti-Castro Spanish teacher.
“Gambino Roche was a Cuban political refugee who taught Spanish at Dalton, although it is unclear whether he possessed any teaching credentials or experience,” Mark Robinson, class of ’74, wrote in an unpublished memoir about his time at the school. “Señor Roche had unabashed disdain for Dalton’s spoiled, soft, leftist rich kids. And this was, I believe, a big part of his appeal to Donald Barr.”
Epstein was another outsider. His Brooklyn accent stood out among the children of the Upper East Side elite; he’d been raised in the gated community of Sea Gate in Coney Island, the grandson of Jewish immigrants. He was a talented pianist and gifted student, smart enough to skip two grades at Lafayette High School in Brooklyn’s Gravesend neighborhood.
“Epstein, as a kid, was chubby, with curly hair and a high, ‘hee-hee’ kind of laugh,” childhood friend Beverly Donatelli told James Patterson for Filthy Rich, his book about the Epstein case. “He tutored my girlfriend and myself in the summer. He taught me geometry in just two months.”
Those skills must have caught the eye of someone in the school’s administration. The hiring process was simpler, and more unconventional, at Dalton, which is consistently ranked among the top private day schools in the United States. “The thing about a private school is that you don’t have the same kind of accountability as you do at a public school,” says Gitelle. “We had a lot of teachers who had different kinds of backgrounds. It felt very laissez faire.”
Mark Robinson was in the first wave of black students at the school, and as the only student switchboard operator, he came to the headmaster’s attention. “Barr admired and liked the minority students better than he liked the rich white kids,” recalls Robinson. “My impression of him at the time was this is a really smart guy who is at a party he doesn’t like.”
Robinson had his own culture shocks, coming to Dalton from a New York public school. “Us black kids had zero opportunity to compete,” he says. “They would talk about, in a very competitive way, things they did or could do or spend money on. Dalton is the first time I heard ‘summer’ used as a verb.”
But if there were at-risk kids of the sort Epstein was reported to be interested in, they didn’t necessarily come from the working classes. “There’s stereotypical assumption that the minority students were from broken families and single-parent households,” says Robinson. “Most black kids at Dalton came from fairly healthy nuclear families, whereas it was pretty commonplace for white kids at Dalton, and particularly the wealthier white kids at Dalton, to come from broken families. You had kids who were raised by nannies or whose father was in his 60’s, on his third wife, and he didn’t spend time with you.”
The connections Jeffrey Epstein made while at Dalton set him up for life. He was tutoring the son of Alan “Ace” Greenberg there when the Bear Stearns honcho took a shine to the outsider. “Greenberg didn’t care about MBAs or Ivy League diplomas,” writes Patterson. “What he cared about was raw talent and drive. Greenberg cultivated risk takers, unconventional thinkers, and he looked high (and especially low) for his PSDs: men who, in his estimation, were poor, smart, and, above all, determined.”
Epstein left the investment bank under murky circumstances (Greenberg has since died, and Bear Stearns collapsed in the midst of the subprime mortgage crisis of 2008) and soon was making a tidy living the old-fashioned way, helping super-rich people find inventive ways to avoid paying income tax. It was his association with Ohio-based Les Wexner, founder and CEO of L Brands (Victoria’s Secret, Henri Bendel) that secured his fortune. He made hundreds of millions managing Wexner’s billions, bought mansions in NY, Paris, and Palm Beach, and Little Saint James in the US Virgin Islands. The staff at his private island called his retreat (the site of many alleged orgies involving underage girls) “Little Saint Jeff’s,” while the jet that brought them was dubbed “The Lolita Express.”
Nabokov’s not smiling anymore.
His teaching stint would hardly rate a line on Jeffrey Epstein’s resume. School officials have suggested that he didn’t stay at Dalton longer because he just wasn’t that good a teacher. But his position in the firmament there was telling: Epstein was an outsider looking in at Dalton. For an outer-borough boy like him, those cute young girls must have looked like so many puff pastries, as he pressed his nose against the glass of one of Manhattan’s most elite schools. You can look at his future acquisitive behavior in the same light. The $56 million mansion he bought on East 71st Street, not far from the Dalton School, is said to be the biggest in New York: 21,000 square feet, five bathrooms, with a two-story reception hall. The front door looks like something out of a medieval castle, and when feds broke it down in July, they discovered thousands of pornographic pictures of underage girls (not to mention cash, diamonds and a passport under a different name).
It was there, in 2010, that an assortment of boldface names attended a party Epstein threw in honor of Prince Andrew. Epstein had just completed his brief, and controversial, stint in a Florida jail (he served 13 months for soliciting prostitution, after Florida police built a painstaking case against him for sex-trafficking minors, and was able to leave the Palm Beach County lockup 12 hours each day). Among the attendees were Katie Couric, Charlie Rose, Chelsea Handler and… Woody Allen. Somewhere along the line, the two Brooklyn boys had become fast friends, and small wonder: The filmmaker came from Coney Island and probably recognized a fellow outsider in the financier; Epstein kept a photo of Allen in his study.
Did they ever talk about Dalton? A few jokes about the girls there, back in the day? A lot of people point to the decade when Epstein taught there as an outlier. I heard “That Seventies Excuse” often when writing a book about the Horace Mann School’s sex scandals (Great Is the Truth, with HM alum Amos Kamil): Drugs and bodily fluids were being shared by everyone; rich kids were partying with adults at Studio 54 and CBGB’s; celebrities were hitting on them on the dance floor. Mores were in flux, apologists said. It was a simpler time, when a story about a middle-aged man having sex with a minor could be made palatable with the addition of Gordon Willis’s black-and-white photography and George Gershwin’s music.
(Dalton’s problems may not have ended with that decade. Gardner Dunnan, the school headmaster who followed Barr, was recently sued for sexually assaulting a 15-year-old Dalton girl in 1986. It gets worse: The former student, identified in the complaint by the initials “JS” was a disadvantaged kid who lived with Dunnan as a “family helper” in his home a few blocks from campus. Dunnan denies the charges but was forced to resign in 1997, due in part to an affair he had with a married teacher there.)
Decades later, in 2018, Babi Christina Engelhard came out as one of the inspirations for Allen’s teenage lover in Manhattan. She was 16 in 1976, and caught the eye of the filmmaker when she was at Elaine’s, she told the Hollywood Reporter. She left him a cheeky note (“Since you’ve signed enough autographs, here’s mine!”) that included her phone number. Allen called soon thereafter, Engelhardt claimed, and they began a torrid sexual relationship months before she was 17, the age of consent in NY.
Engelhardt, who went on to a career in modeling, said she assumed that she was just one of several underage girls Allen saw, and the character Mariel Hemingway plays in Manhattan was a composite. (“Great artists cherry pick,” she said, with unintended irony.) She went on to work for Federico Fellini, one of the Allen’s heroes, and then at some point worked as an assistant to… Jeffrey Epstein. She has not commented on the relationship between the two men, or her time working for the financier, and the connection may be no more than coincidence. Engelhardt would have been way past high school when she met Epstein, and was probably of little interest to him sexually. Besides, as Mariel Hemingway tells Woody’s at the end of Manhattan, “Not everyone gets corrupted. You have to have a little faith in people.”