The Harvard-trained lawyer behind Trump's fight against top universities

Washington: When President Donald Trump wants to rattle academia, he turns to his deputy chief of staff, Stephen Miller. And then Miller turns to May Mailman.

Mailman, 37, a Harvard-trained lawyer, is the most important, least-known person behind the administration's relentless pursuit of the nation's premier universities. The extraordinary effort has found seemingly endless ways to pressure schools into submission, including federal funding, student visas and civil rights investigations.

Her hand in deploying these levers of power was evident from the beginning of Trump's second term. As his ambitions around reshaping higher education expanded, so did her remit. She is credited as an animating force behind a strategy that has intimidated independent institutions and undercut years of medical and scientific research.

The policies Mailman helped devise -- and is now leveraging as she leads the White House's negotiations with colleges -- have sent shock waves through higher education, dividing faculty and alarming some students who see an effort to silence dissent. The aggressive tactics could have far-reaching implications for the future of academic freedom, the admissions practices at the most competitive colleges and the global reputations for some of the crown jewels of the nation's university system.

So far, only Harvard has been willing to fight back in court, a sign of the strength of the federal government's negotiating position.

"There are a lot of good ideas floating around this building, but somebody has to capture those ideas, make sure that the right people are involved and that there is a process to put them into action," Mailman said in a recent interview at the White House. "So I'm the catcher of floating ideas."

She glanced up from her hands, folded in her lap.

"Although," she added, "I try to have some good ideas of my own every once in a while."

Mailman wrote the executive orders Trump signed on his first day in office that redefined the federal government's stance on sex to acknowledge only two genders and dismantled policies aimed at promoting diversity, equity and inclusion. By June, these changes had forced the University of Pennsylvania to align its athletic policies with the administration's view that transgender girls and women should be banned from participating in women's sports.

She had a direct hand in the effort to prevent Harvard from enrolling international students, which unnerved the university's leadership and student body and which a court has temporarily halted. And last month, Mailman closed a $221 million deal with Columbia University, the administration's largest settlement to date.

To understand the scope of Mailman's influence, the Times reviewed emails and other government records surfaced in court cases targeting the Trump administration, mined her interviews on conservative podcasts and other media appearances and interviewed more than a dozen current and former colleagues.

Mailman also agreed to the interview in her West Wing office, located directly next to the office of Miller, just before she stepped down from her position as a White House senior policy strategist, pregnant with her third child. She has continued to take the lead in vexing -- and negotiating with -- universities as a senior adviser for special projects.

The biggest prize for Trump, and Mailman, remains Harvard.

Talks appeared to be moving forward, with the university signaling it was open to spending $500 million to reach a resolution. Still, on Friday, the administration dialed up the pressure once more, with a new investigation involving patents that the university derided as "yet another retaliatory effort targeting Harvard for defending its rights and freedom."

A Bush admirer heads to Trump's White House.

Mailman said she did not join the second Trump administration to take down Harvard, where she mostly enjoyed her time as a graduate student.

Instead, she was recruited by Susie Wiles, the White House chief of staff, and Miller because of her various roles in the White House during Trump's first term. For the second term, she would help with the transition, write Trump's deluge of initial executive orders and help set up a process for turning his campaign promises into policy. She had always planned to depart after six months, she said.

In that time, Mailman became a crucial component of one of the White House's most divisive endeavors -- a sprawling political and legal bid to root out perceived liberal bias from colleges and deter the use of race in admissions.

The gender-based executive orders she wrote prompted opposition from human rights advocates who argued the directives perpetuate discrimination. Student and faculty groups have accused the administration of trampling on the First Amendment in trying to dictate who schools can hire, what students they can admit and which subjects they can teach.

"If you normalize the use of federal power like this, then academic freedom is just a memory and universities become political footballs and no longer useful instruments in the search for truth," said Adam Goldstein, the vice president of strategic initiatives at the Foundation for Individual Rights and Expression, a free speech group.

Inside the White House, Mailman's ruthless efficiency and engaging personality has earned her praise from superiors and loyalty from junior staff members. Despite her fearsome role in dragging university lawyers to the negotiating table, some who have made deals with the government have privately complimented her pragmatism in balancing competing interests within the administration with the universities' needs.

"May has been one of the most indispensable, gifted and dedicated staffers and lawyers in the Trump administration since Day 1," Miller said in a statement.

Born in the South, raised in the Midwest, and educated on the East Coast, Mailman has spent much of her life collecting ideas from disparate places and weaving them together.

Her father, Dr. Duncan Davis, was administering vaccines to children in South Korea in the 1980s when he met her mother, Kyungae Davis, who was teaching in one of the schools he visited. They moved to the United States, married and gave birth to their first child, Sylvia May Davis, in 1988.

The family eventually settled in Kansas, first in Goodland and then in Clay Center, both small, predominantly white towns. In both, less than 1% of residents were Asian, like Mailman's mother, or two or more races, like Mailman.

Mailman said her dark features stood out, and made her an easy target for schoolyard taunts, but she learned to parry by using her wits. She has a blunt and candid conversational style, and an easy proficiency with profanity.

At Clay Center's high school, Mailman is pictured in nearly every activity in the yearbook.

She was also becoming increasingly curious about Republican politics.

At the University of Kansas, where she majored in journalism, Mailman joined the college Republicans. She recalled the surprising inspiration she felt attending a campaign event for President George W. Bush while living in Lawrence, Kansas.

"George Bush's image in the news when I was in college was someone you might get a beer with, but also sleepy and dimwitted," Mailman said. "But then, in person, he felt energetic and warm, and there was an enthusiasm in the crowd. I'm sure it's what people feel going to their first Trump rally. And I started volunteering after that."

In 2012, she enrolled at Harvard Law School, where she was remembered as fun and outspoken by some classmates, and outrageous or over-the-top by others.

After graduating in 2015, she moved to Denver to join a midsize law firm. A former Harvard classmate, William Payne, texted her 15 months later asking if she would like to work in the "center of the universe."

She had no desire, Mailman told him, to move to New York.

Payne said he meant the White House.

During her four years with the first Trump administration, she gained unique access to the president and his aides, including Miller, frequently traveling with Trump and his core advisers.

She left the White House in the days after the Capitol riot on Jan. 6, 2021, took a job as deputy solicitor general of Ohio and married David Mailman, a former baseball player with a corporate job in Cleveland. They moved to Houston, had their first child in 2022 and a second in 2024.

But she was not done with Washington, or Trump.

'The issue picked me.'

In 2024, Mailman was named the director of the Independent Women's Law Center. The center is a project of the Independent Women's Forum, a Virginia-based nonprofit created by a coalition of women who supported Justice Clarence Thomas during his contentious nomination hearings in the early 1990s.

At the law center, Mailman quickly immersed herself in issues that animated Trump's campaign and would deeply inform the domestic agenda in his second term, such as rolling back protections for transgender people. She fought against Biden administration policies that had extended discrimination protections to transgender students. And she focused on the University of Pennsylvania, where Lia Thomas, a transgender swimmer, had broken records on the women's team in 2022. Mailman also represented Allie Coghan, who sued her University of Wyoming sorority in 2023 for allowing a transgender woman into their chapter.

Mailman's work with the group, where she is returning after leaving the White House, landed her on the "hate and extremism" section of the website for GLAAD, one of the country's leading LGBTQ+ advocacy groups.

Mailman said her views on gender aligned with the philosophical underpinnings of her politics, which she described as a kind of libertarianism that abhors political correctness.

"The issue picked me," she said.

In recent weeks, a combination of funding cuts and civil rights investigations resulted in settlements with Columbia and Brown University. Mailman is in active negotiations with other elite schools, Cornell University and Northwestern University, along with Harvard.

She said that whether Harvard was willing to go beyond existing requirements to show how race factored into its admissions process would largely determine whether the government would sign off on an agreement.

"If Harvard wants this deal, then I think the same way that UPenn needed to focus on gender ideology is the same way Harvard needs to focus on racial admissions," Mailman said.

"We don't want to run these universities," Mailman added. "We want some sweeping changes that set things in the right trajectory."