In the winter of 2020, an impassioned debate about anti-racism broke out in Manhattan’s elite private-school community. It started with Dalton when a document, signed by 120 members of its faculty and staff, and featuring 24 proposals intended to help the school move toward its goal of becoming a more “structurally anti-racist institution,” was made public. Suddenly, Dalton parents were speaking out in protest. “Many of us do not feel welcome at Dalton any more,” a group calling itself “Loving Concern @ Dalton” declared. “That really hurts to write.”

Then the floodgates opened. Riverdale was next on the hot seat. Then came Grace Church. And then Brearley parent Andrew Gutmann fired the shot heard round the Upper East Side—a letter alleging that Brearley was not only requiring “unsophisticated and inane” anti-racism training of its parents, but was suffusing its entire community with anti-intellectual political indoctrination reminiscent of China’s Cultural Revolution. (He also claimed, “We have not had systemic racism against Blacks in this country since the civil rights reforms of the 1960s.”) Head of school Jane Fried replied with a letter of her own, calling Gutmann’s letter “deeply offensive” and reiterating her commitment to “build an inclusive, antiracist school.”

While it might have seemed to a casual observer an utterly random grouping of schools that were experiencing the lion’s share of diversity discord, they all have, as it turns out, an interesting, and perhaps critical, common thread. Dalton, Riverdale, Grace Church, and Brearley all use the same diversity, equity, and inclusion consultant, a nonprofit called, of all things, Pollyanna.

The New York City private schools advised by Pollyanna have received both internal and external criticism.

“If you were doing a satire and you had to name the hyper-liberal police, you might call it Pollyanna, because it makes everything, for lack of a better term, seem so black-and-white when you’re talking about an incredibly complex issue,” says a Manhattan private-school parent. But according to Pollyanna Inc.’s Web site, the group is so named as an homage to firm founder Casper Caldarola’s mother, who used to call her daughter “Pollyanna” when she was little because she “always tried to see the best in everyone.”

“I personally don’t agree that that’s true,” says a former Dalton parent who worked with Caldarola—who was herself a Dalton parent as well as an alum—on the school’s Parents Association back in the early 2000s. “She’s a salty dog.”

Caldarola has declined to speak with Air Mail about her organization and the controversy now swirling around it. But the title of an out-of-print consumer guide that she and her mother, an advertising executive, co-wrote and self-published, in 2004, may provide at least a clue as to her capacity for boldness. Its title: How to Bitch and Win!

Dalton Days

When Caldarola graduated from Dalton, in 1977, her name was Shari Casper, and the school was largely white and Jewish. Upon graduation, Casper left the school’s Upper East Side neighborhood for the incomparably liberal wilds of Amherst, Massachusetts, to attend the new, and experimental, Hampshire College, where the faculty has included Diane Arbus and James Baldwin.

By the mid-1980s, Casper was back in New York, working in advertising alongside her Brooklyn-born mother, Diane Casper, who, according to a 1985 New York Times article, referred to herself as “the Disease Lady of Madison Avenue,” because she worked on accounts for a variety of over-the-counter drugs.

With New York deep into its go-go Wall Street boom of the early 90s, Shari Casper married Charles Caldarola and took a job in publicity and special events at the Warner Bros. Studio Store. Eventually she would drop “Shari,” take “Casper” as her first name, and make her husband’s surname her own.

In the mid-90s, Caldarola became a mother and left the workforce. But not long after her son started at Dalton, she became a tireless parent volunteer, embedding herself deeply into the school community with both teachers and parents alike. Years later these connections would turn out to be beneficial. Of the three members of Caldarola’s six-person Pollyanna team who are not high-schoolers, two are former Dalton teachers—Monique Vogelsang, who taught fourth grade, and Jay Golon, who taught middle-school social studies—and the operations manager is former Dalton trustee and current parent Claire Hannan-Radomisli.

Meanwhile, both Pollyanna’s board of trustees and its advisory board have been rife with Dalton parents, including Michele Barakett, a psychologist whose hedge-funder husband, Tim, has served on Dalton’s board and is said to have earned $750 million in 2007 alone; Tal Recanati, a film producer and entrepreneur, whose shipping-C.E.O. husband, Ariel, is a member of a prominent Israeli family; and Deborah Roberts, the ABC News journalist married to Today anchor Al Roker.

According to the Pollyanna Web site, Caldarola, while president of the Dalton Parents Association, a position she held from 2005 to 2008, “created a more inclusive community and developed a new budgeting structure making it possible for parents of different socioeconomics to volunteer.” But according to the parent who worked with her on the Parents Association, the statement makes little sense. “You didn’t have to give money to join,” she recalls. “I remember a woman who wanted to do it. She lived in the Bronx, worked downtown, and was a single parent. She had to quit the P.A. board.... It’s a real luxury to be able to sit around in the cafeteria.”

Talking the Talk

By the time she became head of the Dalton Parents Association, Caldarola was back at work, having taken a job as director of communications at the all-boys Allen-Stevenson School in 2000. Eventually her portfolio expanded to include co-creating the school’s Community Life + Diversity department, and it was there that she gained experience creating professional development for teachers that included workshops on white privilege, affinity groups, and how to build an inclusive classroom. At the time, in the private-school world, these were relatively novel concepts and content, all of which would later play a role in the pedagogy of Pollyanna.

In 2005, while still working at Allen-Stevenson, Caldarola joined the Dalton board of trustees, on which she served for a decade. In 2015, Caldarola founded the nonprofit Pollyanna. According to a Dalton parent, during an online racial literary workshop for parents that was held this past February, the Dalton lower-school head called it an extension of the school.

This impression is only furthered by Pollyanna’s Web site, which bore, up until recently, a glowing testimonial from none other than Dalton headmaster Jim Best: “Pollyanna is transformative. You’ll talk the talk, you’ll walk the walk, and you’ll see the world—and your work—in a new light.”

Just last month, Best announced that after having worked at Dalton for 16 years, and serving only 3 of them as headmaster, he was leaving his post, which paid him $756,463 in 2019, the most recent year for which tax information is available.

Three weeks ago, in his introductory remarks at the annual Dalton Diversity Conference, Best called his upcoming departure “an elephant in the room.” “To put it plainly,” he said, “no one here, including me, has the full story,” but he went on to share reflections from his experience. “A school in 2021 should not look or feel or operate like a school in 1921, or 1991,” he said. “And yet we need to do the good work of explaining this to our parents, and our alums, and our students, and our trustees … We’re not causing problems, we’re making progress.” (According to a Dalton spokesperson, Best made the decision to leave, and “he is beginning a new chapter in a completely amicable transition process.” What’s more, says the spokesperson, “Dalton’s long standing DEI work—of which anti-racism and anti-bias are components, and is foundational to educational excellence—continues, and the administration has provided regular updates on this work to the school community.”)

Best’s departure after a year of mounting pressures may be a strange form of progress, but if there is a single entity that is the embodiment of it, surely that entity is Pollyanna. For while Pollyanna is the creation of Casper Caldarola, it seems to have equally sprung, like Athena from the head of Zeus, right out of Dalton.

Conference Calls

Take the aforementioned Dalton Conference. As chair of the Dalton board’s “Community Life and Diversity” committee, Caldarola not only worked to create the conference but had also helped to develop the school’s 2007 strategic plan that called for its creation. The idea was for Dalton to host a city-wide conference that would help turn its vision of “an inclusive independent school community” into reality.

Caldarola “put together a huge notebook,” recalls her former Dalton Parents Association colleague. The conference was “physically held at Dalton … and while she was on the board at Dalton. That was her entrée.”

Launched in 2011, the annual conference now has 450 attendees from 30 different New York private schools, and is a day-long program whose planning committee Caldarola chairs. Pollyanna board members Michele Barakett and Rena Andoh, a Dalton alum, serve alongside Caldarola on the committee, as have Monique Vogelsang and Claire Hannan-Radomisli.

Casper Caldarola

Given that Caldarola leads both the Dalton Conference and Pollyanna, it is not surprising that past conference topics have tracked closely with those that animate the nonprofit. But, in fact, the topics for the Dalton Conference and the “Multi-School Conference” package, which Pollyanna offers, are nearly identical. Of the eight topics included in the “Topics for Multi-School Conference,” every one except for the bespoke “Create a new topic for your school” option has already been done at the Dalton Conference. Pollyanna’s Web site does not once credit the Dalton Conference for its content. (“There is no conflict of interest with Pollyanna,” says Dalton’s spokesperson. “Casper Caldarola has never been an employee and just like with any other consultant or vendor, we negotiate a separate contract with her every year. Her work with other schools and business decisions are completely separate matters.”)

In the beginning, Pollyanna was modestly successful. According to the nonprofit’s 2019 tax returns, the company had program-service revenue of $48,250 in 2018, which grew to $269,604 in 2019.

But when the pandemic hit New York, in March 2020, it starkly exposed the city’s vast socio-economic disparities, which had been hiding in plain sight, not least of all within the walls of its most elite private schools. “Twenty years ago,” says a trustee of one of them, “there were plenty of rich people in my kid’s class, but there were middle-class people, too.... There were not a lot of people helicoptering to the Hamptons and having 17-room apartments.”

The city’s private-school heads were now struggling not just to manage the logistical problems that the virus posed for all schools but also to straddle this fault line—balancing the demands of 1-percenter families with the needs of financial-aid recipients, some of whose parents were essential workers, and who would have had to return to in-person classes via public transit.

By spring, many of the city’s emotionally exhausted headmasters, who had taken to having weekly Zoom calls to mutually strategize and commiserate, were looking forward to summer as never before. But then George Floyd was brutally murdered, setting off a wave of protests against racism the likes of which had not been seen since the 1960s.

Suddenly New York City private-school students of color were not only joining in but responding in a way that befitted their online-all-the-time generation: taking to Instagram to post first-person accounts of what it was really like to be Black at these institutions, a movement sparked by a student at Brearley.

From Zeitgeist to Blitzkrieg

“Welcome to Black at the Big B.,” she posted last June 7. “This is a platform for the Black girls who feel silenced. We want to share the stories of Black life at Brearley, in hopes that these stories lead to institutional changes.”

The response was a torrent, with Black alums and students sharing memories of being traumatized by white students—“If citizens had to pay taxes,” one white student reportedly asked in an eighth-grade American-history class during a study of Reconstruction, “wouldn’t Black people want to be slaves so that they could not pay taxes?”—while a former student alleged that a white Brearley college guidance counselor “has a demonstrated history of discouraging Black students from applying to competitive schools,” a post which received several corroborating comments.

The schools “had to do something,” says a Brearley parent, “and then the question is ‘What’s the something?’ … Brearley has had people in these diversity positions, whose job it is to work on these issues in the community, for years. Decades.... If you’re the school, you almost feel obligated to bring in someone from the outside because you have to recognize that whatever you’ve been doing has not been working.” (Brearley declined to respond to specific questions but provided a statement from head of school Jane Fried, explaining that the school’s D.E.I. programming “will evolve as we continue to gather vital feedback from our community on the impact of our initiatives.”)

“As with any other industry,” says the New York City private-school trustee, “people like Pollyanna get hired because they know these institutions. Caldarola went there, had kids there; she knows what the families are like, what the community is like, what the faculties are like. Independent schools are cloistered in their way. They want people who understand their community. That’s how this group has gotten so much work. She’s a known commodity.”

Additionally, Caldarola, like the headmasters themselves, is white. As she wrote earlier this month, in her May Pollyanna newsletter, with regard to the “Circle of Identity,” a common workshop exercise that asks participants to write down five identity-defining words: “I know Mom, Daughter, Woman, Jew and White were always my five words.”

And so, last summer, headmasters across the city began reaching out to Pollyanna in a panic. The diversity, equity, and inclusion Zeitgeist of which Caldarola had been an early proponent had coalesced into something far more pervasive than perhaps even she had imagined. It had coalesced into a blitzkrieg.

Casper Caldarola met her moment.

By fall, Brearley had begun requiring anti-racist training; in fact, two different Zoom (or online) sessions for “at least one parent or guardian from each student’s household, ” an e-mail from the Brearley Parents Association noted. Attendance would be taken, and participants were required to “keep their cameras on and display their names for the duration of the meeting.”

“If you’re the school, you almost feel obligated to bring in someone from the outside because you have to recognize that whatever you’ve been doing has not been working.”

But according to the Brearley parent, who attended Pollyanna’s “Racism and the Brain: How Does Racism Affect Thinking and Learning?” workshop, it really did “make me think differently about what is a micro-aggression.... If you’re an abused person, you’re more likely to flinch.... They literally went to the cellular level of what the synapses do.”

That said, not all private-school parents are so enamored with either Pollyanna or its K–8 anti-racist curriculum, which integrates race into every subject. While some deride this curriculum by saying it teaches critical race theory, that is not correct; rather, critical race theory is its philosophical underpinning.

Critical race theory, or C.R.T., is a school of thought developed by American legal scholars in the 1970s, including Kimberlé Crenshaw, of U.C.L.A. and Columbia University, and Richard Delgado, of the University of Alabama, who were frustrated by the lack of progress toward racial equity in the post-civil-rights era, and so sought to examine how the law intersects with race. Critical race theorists take as a given that white supremacy and systemic racism, which is anti-Black, exist in our society.

Pollyanna’s “Racial Literacy Curriculum” begins in kindergarten with a “celebration of skin colors” that is both metaphoric and literal, with children mixing paint to create various skin colors, including their own, and parents and guardians, as per Pollyanna’s “Companion Guide,” encouraged to “model for their child how they take care of their own skin, such as routines that encourage cleanliness, moisturizing, protection from the elements etc.,” and to discuss variations in skin color.

But while some of the curriculum does not seem to be particularly unique—encouraging children to “embrace the concept of family,” fill one’s bucket with compliments and positive actions, explore what makes their neighborhoods “special or different”—it evolves, in the higher grades, into lessons about slavery, colonialism, and immigration.

But according to a Dalton parent who is considering switching schools, a Pollyanna representative asserted, at an online Dalton parents’ presentation that the parent attended last fall, that “there’s clearly white supremacy everywhere,” citing U.S. immigration laws as proof without making a coherent case.

“They talk about immigration policy with an appeal to Asian-Americans by talking about the Chinese Exclusion Act of 1882, saying, ‘Aha!, white supremacy has always been in the fabric of America,’” this Dalton parent says. “The problem is it’s without context. This Pollyanna curriculum specialist is a former middle-school teacher who is not an American-history scholar. Does she know that in the middle 19th century, right before this, there were exclusion efforts for Southern Europeans who were considered not white and for Irish Catholics too?… Kids will think this adult is right because Dalton is putting them in front of me and they are facts. And they are facts. They’re googleable.... But a selective magnification of warts is very different than teaching history ‘warts and all.’”

There may be an additional element at play in the controversy over recent diversity, equity, and inclusion efforts—white, upper-class angst about the possibility of their dominant position in American society being undermined by progress toward a more equitable future. Especially in the realm of college admissions, which, for many private-school parents, is the end game. What if it turns out that spending $50,000-plus for 13 years straight does not guarantee admission to an elite university?

“This year,” explains the private-school trustee, “across the country, the admissions rates at the top 20, 50, colleges shifted. People who were legacies, people who got in because there was a donation or they knew somebody … those numbers just aren’t the same. Colleges have been very cognizant just like everyone else to be more equitable in who they’re admitting, and that has not sat well with parents who have paid all this money. ‘My kid’s not going to Yale, but they have to go to Middlebury? Oh my God, my life is ruined!’ There’s some of that. And I just think there’s more under-the-radar racism than any of us in liberal old N.Y.C. want to believe.”

Johanna Berkman is a New York–based writer