May Mailman has become a significant yet under-the-radar figure in U.S. higher education policy during her tenure in the Trump administration. The Harvard-trained lawyer has been instrumental in formulating policies aimed at some of the nation’s most esteemed universities, challenging long-standing core values such as academic freedom and diversity initiatives.
In August 2025, Mailman stepped down from her role as deputy assistant to the president and senior policy strategist. While she has left her official position, she continues to play a role as a special government employee, engaged in critical negotiations, including discussions with Harvard University about halted federal research funds. She is also laying the groundwork for a government affairs firm but has pledged not to undertake projects related to her previous work with the administration.
Born in 1988 as Sylvia May Davis, Mailman grew up in predominantly white towns in Kansas. Her parents met in South Korea and later moved to the United States. Growing up among few peers of Asian descent, she faced early social challenges but developed a sharp wit and a direct way of expressing her views. Mailman’s political journey began at the University of Kansas, where she majored in journalism and participated with the College Republicans. A pivotal moment in her political awakening came from attending a George W. Bush campaign event, shaping her perception of Republican leadership.
After earning her law degree from Harvard in 2015, Mailman initially worked at a mid-sized law firm in Colorado. Her trajectory shifted as she was recruited to the White House during Trump’s first term, where she held various positions, including roles within the staff secretary’s office and White House counsel’s office. This experience afforded her unique access to top advisers and frequent opportunities to travel with the president.
Upon returning to Washington for Trump’s second term, Mailman focused on transforming campaign promises into actionable policies. She played a key role in developing executive orders that redefined federal approaches to gender and diversity, impacting universities like the University of Pennsylvania and Harvard. Her efforts have been considered instrumental in aligning federal influence with conservative educational policies, especially in relation to admissions and athletics.
Mailman’s political views reflect a libertarian skepticism of political correctness, favoring positions that oppose transgender protections and affirmative action. Despite the controversial nature of her policy work, colleagues commend her as an adept and effective negotiator. In addition to her professional commitments, Mailman balances a busy family life as a mother of three.
The influence of Mailman and her policies on higher education may continue to be felt in the coming years, as debates over academic freedom and diversity initiatives persist in the national discourse.
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