In recent years, Milton administrators and Head of School Alixe Callen ’88 have begun laying the groundwork for a fundraising campaign to combat a roughly $1 billion endowment gap between Milton and its peer schools Phillips Academy Andover and Phillips Exeter Academy. Andover’s and Exeter’s endowments stand at around $1.47 billion and $1.65 billion, respectively, while Milton’s is currently $450 million. Given that Exeter and Andover enroll about 1,100 students to Milton’s 750 Upper School students, Andover and Exeter hold about $900,000 more in endowment per student than Milton. Assuming an annual draw of 4.4%, Callen calculated that the two schools “have about $44,000 more per kid to spend” each year. “That’s a significant difference,” she said.
Callen confirmed that the school is “still in the planning phases” of a campaign, from which she hopes to finalize a new strategic plan that has been under discussion with faculty and other stakeholders for over a year. Now in her fourth year as the Head of School (after transferring from St. George’s School in 2023), Callen explained that new heads typically spend a year getting their “feet wet,” after which “generally a campaign will follow.”
Executive Director of Development Carol Giusti-Cahalane echoed this sequence, noting that whenever an institution introduces a new strategic plan, “there will be a campaign that is aligned with it.” Giusti-Cahalane underlined that the administration is “planning … and having those conversations now,” but will not launch the campaign publicly “for a couple of years, maybe even longer.” Both she and Callen cited how campaigns usually begin with a “quiet phase,” in which the school plans only with its closest donors; Giusti-Cahalane revealed that the school typically raises 50 to 75 percent of a total fundraising goal before the campaign opens to the entire community in a “more celebratory” final push.
Neither administrator would speak in detail to Milton’s fundraising history, though both pointed to its peers’ stronger efforts in the past. Giusti-Cahalane speculated that “historically we just didn’t do as strong a job as places like Andover and Exeter,” highlighting that the larger schools have broader alumni bases and “a bigger machine of people going out there and doing the work.” Callen similarly reflected that the other schools “were doing something differently than we were back in the day.”
The record supports Giusti-Cahalane’s guess. According to Milton Academy’s website, the Dare campaign, which raised $183 million between 2013 and 2020, was “the school’s first comprehensive capital campaign.” By then, Milton’s peers had been fundraising for generations: Exeter’s annual fund dates back to 1922, and Andover’s most recent campaign alone raised $408.9 million.
Students, however, noticed the gap in different ways. Allegra Feldman ’28, for example, felt that “sports-wise we’re a little underwhelming” when speaking to Milton’s facilities, and though Chloe Clayton ’29 felt the same way, she attributed the difference to size, explaining that Andover and Exeter “get a lot more donations…[and] alumni.”
However, Callen maintained that this gap does not put Milton in any financial danger. “Many, many schools would say that a $450 million endowment is enviable,” Callen said. “To say that we’re hurting … would not be the case.” Instead, Callen emphasized that “financial sustainability for any school, like ours, is something that you have to pay attention to.”
Still, tuition alone does not cover the cost of a Milton education. In a March interview with The Measure, Chief Advancement Officer Kelly DeGregorio explained that “tuition only covers about 75 percent of what it actually costs to provide a Milton education.” Giusti-Cahalane offered a similar breakdown, citing a 72 to 73 percent tuition coverage of costs, a Milton Fund contribution of seven to nine percent, and the endowment and other revenue covering the remainder. Callen estimated that each student costs “$25,000 to $30,000 more” than tuition pays for and must be financed from “some place.” By contrast, Andover’s official website says its endowment alone has funded about 45 percent of the school’s annual expenses over the past decade.
This figure surprised some students in opposite directions. Samuel Greer ’27 found 75 percent “a little lower” than expected and, while opposing any tuition increase, argued that Milton should not “depend so much on donations.” On the other hand, Clayton had expected donors to carry more of the financial burden, admitting that she “thought that the alumni were a bit more giving.”
The Milton Fund, Callen noted, “broke $7 million last year,” up by more than $1 million. This signals “growth in our fundraising program.” Giusti-Cahalane stressed that the endowment plays an equally important role in keeping tuition “as reasonable as we can,” warning that without an endowment, “tuition would skyrocket even more.”
Raising that money, however, has become much more competitive in recent years. Giusti-Cahalane explained that the challenges Milton faces are “not unique to Milton,” as universities have increasingly turned to alumni since federal research funding dried up under Trump administration policies. Milton also competes with healthcare, research, and community-based nonprofits for a finite sum of donation monies, and younger donors “really want to see the impact” of their gifts. For this reason, students and their impact in the world are “our greatest resource when we talk about fundraising,” Giusti-Cahalane said.
The Development Office plans to build its message around Callen’s emerging vision of Milton as “a hub for bold ideas,” with students “grounded in knowledge, ethics, and agency.” Fundraising priorities will focus on student support, faculty support, and programs such as the interdisciplinary centers Callen has proposed.
Ultimately, to Callen, the fundraising campaign–though Giusti-Cahalane suspects it will not go public until after 2028–is more than buildings. “Milton sends people out into the world who change the world,” she said, describing each gift as “an investment.” If the endowment grows, Callen said financial aid would likely receive the largest share. “To ensure that students have access to Milton, regardless of their ability to pay, is something that’s really important to me,” she said. According to Milton Academy’s website, 37 percent of its students currently receive aid, and the school meets “100% of the demonstrated need” of each enrolled student. By comparison, “almost half” of Exeter’s students receive financial aid.
Yet not every student is fully convinced. Greer noted that he would “probably give [his] money to a charity before [he] give[s] it to a school like this because we have a pretty nice campus,” and he believes that there are “people who need money more than we do,” underscoring the very competition with charities and community nonprofits that Giusti-Cahalane acknowledged, and the challenge Milton faces in convincing its own students to give back.