WASHINGTON — When she graduated from Harvard Law School, May Mailman didn’t expect to find herself one day representing the White House on the other side of a high-stakes negotiation with her alma mater. In fact, she enjoyed her time at the university and the opportunities she had there.
But as a senior policy official for President Trump, Mailman has become a point person on the administration’s campaign to bring higher education to heel, telling the Globe in an interview that the administration’s goal is to make Harvard better.
“It doesn’t feel like I’m against Harvard,” Mailman said. “It feels like this is a moment for them to say out loud, ‘These are our values.’”
To get Harvard to that point, the administration has implemented a multipronged pressure campaign that includes canceling nearly $3 billion in federal grants, attempting to block visas for international students and staff, and threatening the university’s accreditation.
Mailman, a 2015 law school graduate, is the White House’s senior policy strategist and a deputy assistant to the president. She is a right hand to deputy chief of staff Stephen Miller, atop the nerve center of the White House on Trump’s policy priorities. That includes Trump’s current campaign against Harvard and other universities under the stated objective of ending diversity policies the administration considers discriminatory and combating antisemitism, particularly the protests and environment on campuses since Hamas’s 2023 attack on Israel and the ensuing war in Gaza.
While Mailman credits other officials across the administration with coming up with many of the measures so far, she coordinates and spearheads the execution of Trump’s vision and ideas.
Her role as a central player in the high-stakes confrontation has emerged from interviews, press accounts, and internal documents unearthed during legal challenges to the administration’s canceling of funding.
Mailman, 37, declined to discuss what the administration specifically wants from Harvard, but she pointed to other universities’ settlements as a roadmap.
“There’s almost a fear of [reaching an agreement] because it might be seen as too pro-Trump,” Mailman said. “And it’s like, don’t be scared. Penn survived it. Columbia survived it.”
Columbia University, an early target of the administration, this week reached a settlement with the administration to restore federal funding in exchange for a payment of more than $220 million to the government and a wide range of campus policy changes. Both sides claimed victory with the deal, which included a provision that said the agreement should not “be construed as giving the United States authority to dictate faculty hiring, University hiring, admission decisions, or the content of academic speech.” The University of Pennsylvania also settled recently with the administration in a civil rights case over transgender athletes.
Harvard has taken a different approach. It rejected the Trump administration’s demands in April to overhaul its hiring practices, admissions policies, and governance — calling them an unconstitutional attempt to control a private institution — and has sued the government over canceled research funding and efforts to bar international students.
Mailman cited the Columbia agreement as showing the administration’s priorities: “quality and fairness, a commitment to ending racial hierarchies, but an equal commitment to academic freedom and freedom of speech.”
“There is nothing in that deal that would constrain academic freedom or freedom of speech, or micromanage the university,” she continued.
Harvard declined to comment on Mailman or the negotiations.
Though she makes frequent media appearances, Mailman is a lesser-known member of the administration. A Trump veteran from his first term, she left Washington after he left office, eventually settling with her husband and two small children in Texas, where her family still lives. She initially resisted joining the White House again, but Miller recruited her back and she commutes between D.C. and Texas each week.
She will soon be stepping down from her current role and moving back home, but she intends to continue working for the administration on issues including higher education in a more limited capacity.
Interviews with eight former classmates, friends, and former colleagues describe Mailman as a smart, energetic, amiable, driven person who doesn’t suffer fools.
They describe her as an intellectual conservative who is passionate about effectuating change in the world, but not a longtime activist looking for a political career. Her entree into Trump’s West Wing came after a Harvard Law School classmate connected her with the administration.
She was working for a law firm in Denver after an appellate clerkship when a fellow Harvard Law alum reached out and notified her that his colleague, Rob Porter and Trump’s new staff secretary, was hiring.
“He texted me and said, ‘Do you want to work in the center of the universe?’” Mailman recalled. “And I said, ‘I hate New York,’ and he said ‘No, the White House.’ And that was it.”
Derek Lyons, Mailman’s former colleague from the first administration, said she impressed the team immediately with her résumé, interview, and readiness to move to D.C. from Denver within days of getting a job in Porter’s office.
“She won people over with high competence, enormous drive, strong work ethic, and high energy,” Lyons said. “She was often seen as somebody who could execute at a very high level under intense time constraints. She’s an excellent lawyer, but also understands policy nuances and political nuances.”
A Kansas native “who came from nothing from the middle of nowhere,” as she describes it, Mailman has a bachelor’s degree from the University of Kansas, served two years with Teach for America, and has a master’s degree in elementary education and teaching from the University of Missouri-St. Louis.
She entered Harvard Law School in 2012 and became president of the school’s chapter of the Federalist Society, a network of conservative and libertarian-minded lawyers, as well as an executive editor at its affiliated law journal, the Harvard Journal of Law & Public Policy. The Federalist Society is well connected to Trump and prominent Republicans and is known for training conservative jurists, including many who get prominent judgeships. Harvard Law is not her only Boston connection. Her husband, David Mailman, is a former baseball player who was drafted by the Red Sox and played in its farm system.
Mailman said that during her time at Harvard, the class did not feel divided by partisanship even though students had different leanings, a sentiment shared by her classmates who spoke to the Globe. Mailman had and maintains friendships with political liberals.
In the years since, however, she said Harvard and other top institutions have lost their way, coddling students and “glorifying victimization” to create a culture that isn’t producing resilient leaders. She is particularly passionate about rooting out diversity initiatives — which some in her orbit attribute in part to her own self-made biography, strong belief in meritocracy, and distaste for elitism — as well as advocating for barring transgender people from domains historically reserved for women. Between administrations, she litigated on that issue with the Independent Women’s Forum, a conservative-leaning advocacy organization. She authored the Trump administration’s day one executive order on recognizing only two genders.
She didn’t seek out her role in the Harvard talks, but nevertheless embraces it. Ultimately, she said, the administration and Harvard largely want the same things.
“I think Harvard thinks that it is excellent, I think it wants to be excellent, I think it knows what excellence looks like,” Mailman said. “I think there’s some desire to not be seen as a Trump lackey or bend the knee to Trump, and like, whatever, do what you need to do to have the [messaging] that you need.
“But at the end of the day, I think it should be the case that our vision and their vision is the same, which is: How do we create the next generation of great leaders, science, and medicine.”
Mike Damiano of the Globe staff contributed to this report.
Tal Kopan can be reached at tal.kopan@globe.com. Follow her @talkopan. Aidan Ryan can be reached at aidan.ryan@globe.com. Follow him @aidanfitzryan.