In late January, months of feuding at New York City’s Dalton School spilled into public view. In an anonymous letter, a group of alumni and parents wrote that the school they had long loved was abandoning real education in favor of “an obsessive focus on race and identity” in every class.

In particular, the letter’s authors blame Pollyanna, a New York-based Diversity, Equity, and Inclusion (DEI) nonprofit. The consultancy’s “racial literacy” curriculum, the letter claimed, “has already permeated Dalton classes from social studies to science” and contributed to “some of the worst abuses this year”—incidents like the one in which a Jewish student was forced to play the “racist cop” in science class, or the art class on “decentering whiteness.”

Pollyanna may be new to outraged parents, but it is familiar to the New York prep school community. Over the past several years, Pollyanna has spread quietly through the toniest schools in New York City and across the country. Buoyed by last summer’s protests, it tripled its clientele to over 60 schools in 2020, stretching from Harvard-Westlake in Los Angeles to remote Vermont Academy. That includes some 25 schools in New York—hyper-exclusive institutions like Dalton, Horace Mann, Spence, and the Hunter College Elementary School.

Pollyanna founder Casper Caldarola declined a request for comment, citing a policy of not discussing “personnel” or “financial” matters, but she told me that “some feel our work is divisive. We couldn’t disagree more strongly. Rather, at its core, our work is an extension of each school’s unique mission, values and vision—their very defining principles.”

If this is true, it is because Pollyanna has perfectly positioned itself to take advantage of the prep world’s new obsession with “antiracism.” Its pricey services and employees’ apparent lack of qualification—other than, as one anonymous parent put it “hold[ing] true to the idea that white people suck”—seem no obstacle to principals and staff eager to prove their $50,000-a-year schools’ concern for social justice.

Race-focused progressivism has long simmered at America’s top prep schools, where it helps the left-leaning clientele reconcile their professed egalitarianism with the hefty tuition bills they pay. But that simmer became a boil last summer, as nationwide protests inspired students to ferret out racism in their own communities. Many launched Instagram pages, on which they anonymously accused peers and teachers of bigotry, ostracizing anyone who spoke or thought in an unacceptable way.

“Kids are very aggressive now in their views, and pushing kids to other views,” one New York parent told me. “The kid-to-kid thing is pushing that, effectively—have you heard the term ‘cancel culture?’ Effectively, if you’re not with us, you’re against us, and you’re the problem.”

Faced with this behavior, administrators neither stood up to the bullying nor investigated the charges. Instead, they doubled down on DEI.

“When there were allegations that there had been kids who had been sexually abused in [the] past, they hired a high-powered law firm, they investigated, they said ‘here’s what happened, we’re going to do everything we can to make sure this never happens again,’” one parent at the Brearley School, one of Polyanna’s “school partners,” said. “If someone at Brearley mistreated or engaged in bad behavior, of course they should be disciplined, fired, you name it. But there was nothing like that. Instead there was this, ‘oh my God, we’re this racist school, so now we have to be antiracist.’”

The Brearley School, which did not respond to a request for comment, plastered an “anti-racist statement” across its homepage—a now-common prep school practice. But they needed to know how to put that promise into practice. Evidently, someone told them to ask Casper Caldarola.

Caldarola, a long-time presence in the New York prep scene, seems well-positioned to take advantage of this moment. Since 2011, she has organized popular diversity conferences at Dalton, out of which Pollyanna grew. She also spent nearly 20 years managing communications and diversity at East Side prep school Allen-Stevenson, until she left in 2018 to focus full-time on Pollyanna.

Caldarola claims no formal training in education (she was an advertising executive before Allen-Stevenson), but she does know people. Pollyanna’s donors are drawn from her prep-world connections, like Dalton head of school Jim Best or Jennifer Vermont-Davis, diversity chair at Allen-Stevenson and a Pollyanna advisory board member. Pollyanna’s only named institutional backer, the Stavros Niarchos Foundation, is run by donor and former Dalton board member Andreas Dracopoulos. Pollyanna’s employees also come from the Dalton community, including a Dalton parent, a former middle school director, and even a former fourth-grade teacher. (Two previously listed employees are also Dalton-linked.)

Such links, the Dalton parents and alumni wrote in their anonymous letter, “suggest a potential conflict of interest, or at least a muddling of priorities and missions.” Dalton denied that there was any conflict; Allen-Stevenson declined to comment.

Brearley is one of more than 40 schools to partner with Pollyanna since last July, including 19 in New York City. Pollyanna offers these clients services including DEI “assessments” and workshops on topics like “microaggressions” and the pseudoscience of implicit bias. Grace Church School, for example, has contracted with Pollyanna to conduct an assessment, while a number of schools, including Dalton and Allen-Stevenson, are incorporating the “racial literacy” curriculum into their classes.

Brearley has made Pollyanna workshops mandatory for students and parents. Seventh and eighth-graders now take classes that encourage them to begin thinking about themselves through the lens of “intersectionality.” Brearley parents are required to attend at least two sessions of Pollyanna-run “antiracism and anti-bias training” on topics like “antiracist strategies for family allies, activists and co-conspirators” and how to “create and sustain antiracist homes.”

The Brearley parent said of the workshops: “the phrase struggle session comes to mind.”

Much of the content Pollyanna offers is based on its “racial literacy” curriculum, a suite of lesson plans imbued with the latest in pop progressivism. The curriculum offers middle-schoolers a heavily slanted history lesson that calls racism a “primary institution” in the United States. Thin on academic references, it relies instead on popular articles and left-leaning commentators from Robin DiAngelo to Howard Zinn. The course begins in kindergarten and culminates in eighth grade, when students spend class time on “racial and/or social justice” projects, turning their lessons into activism.

The suite of lessons was designed by “curriculum specialist” Monique Vogelsang, the former Dalton fourth-grade teacher who now regularly presents at Pollyanna workshops and conferences. Vogelsang has frequently identified herself as a “certified racial literacy trainer,” a designation that, until recently, her LinkedIn profile claimed came from the University of Pennsylvania Graduate School of Education. A Penn GSE spokesperson, however, told me that the school has neither a certificate program in racial literacy training nor any record of Vogelsang attending. Vogelsang ignored questions about this discrepancy but changed her LinkedIn page to cite completion of 30 hours of “racial literacy training” from the Racial Empowerment Collaborative, a Penn-based center that offers continuing education for teachers, among other initiatives. The REC also reported that it had no record of any involvement with Vogelsang, who did not respond to requests for follow-up comments. (Update, March 2022: Almost a year after publication of this article, legal representatives for Vogelsang connected City Journal with Dr. Howard Stevenson, who runs the REC program and confirmed her participation in his brief course.)

It’s not clear if anyone working for Pollyanna can claim substantive credentialing in topics like education, curricular design, or child development—the staff boasts few related academic credentials, and claimed experience is often drawn from volunteer work in the DEI space. Caldarola has no formal training. Jessy Molina, who runs workshops, has degrees in African-American studies and law, which are not obviously related to her work as a DEI consultant. Special Project Manager Jay Golon has a one-year master’s in education, likely a credential needed for his work as an administrator.

“I just think that they’re grossly misguided and eminently unqualified,” one New York City prep parent told me. “There isn’t anyone on their board or in their organization that seems to have the qualifications that one would need, other than people that hold true to the idea that white people suck.”

None of this has stopped schools from paying Pollyanna. While the racial-literacy curriculum is free, invoices I’ve obtained show that a three-hour Zoom session explaining the curriculum costs $5,000, as did a professional-development seminar, administered by Vogelsang, on “the history and impact of systemic racism.” (Asked about the payments, Needham superintendent Dan Gutekanst told me, “this cost for these two workshops, which in my view were incredibly well-done, comes out to like $5.40 a person, and when I think about that, and the benefit to the entire staff, to our increasingly diverse student body and families, I say that I can live with it.” Aveson Charter School did not respond to a request for comment.) Comprehensive assessments like the one Grace Church is undergoing have netted other consultancies hundreds of thousands of dollars.

Those fees explain the nonprofit’s profits. According to tax filings, Pollyanna collected over $250,000 in program revenue in 2019, more than five times its 2018 total and at least ten times that of prior years. Figures for 2020 are not yet available but will likely show similar growth.

That administrators at pricy prep schools are willing to shell out these sums is hardly surprising. That they are willing to pay a group that seems to trade more on its connections than its credentials is more alarming, especially given what Pollyanna actually teaches.

Pollyanna’s meteoric rise, then, says a great deal about the new fad sweeping New York’s elite schools. Administrators seem to be reaching not for the best in diversity training, but for the closest at hand and most extreme. In so doing, they risk cultivating an increasingly toxic culture among faculty, staff, and students—one that propagates bullying in the present and untold consequences in the future, as today’s learners become tomorrow’s leaders.

Photo: Jim.henderson / Creative Commons


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