May Mailman: From Small-Town Roots to Power Player Behind Trump’s Education and Gender Policies

Who is May Mailman, and why is she quietly one of the most consequential figures in today's political landscape? A deep dive reveals how this Kansas-born Harvard Law graduate transformed into a strategic architect of some of the Trump administration’s most controversial policies—while keeping her name out of headlines.

From Goodland, Kansas to Harvard Law

Raised in the tight-knit community of Goodland, Kansas, Mailman grew up in a rural setting where “everybody knew everybody.” Her mother hailed from Korea, and her father worked as a doctor. As a child, participation in 4-H shaped her early years—she recalls wrestling with untrained pigs at livestock shows and learning resilience in unexpected ways Independent Women's Forum.

After earning a B.S. in Journalism at the University of Kansas, she spent time teaching sixth grade through Teach For America—a surprising choice for someone later aligned with conservative circles, but one she embraces as rooted in individual responsibility Independent Women's Forum. She then achieved her J.D. from Harvard Law School, where she notably served as president of the Federalist Society chapter Independent Women's Forum.

A Strategic Legal and Policy Career

Mailman’s public service began with a prestigious clerkship on the Tenth Circuit Court of Appeals before joining the White House in 2017. Starting in the Staff Secretary’s office—where she managed the flow of documents to the Oval Office—she quickly rose to become a legal adviser on issues ranging from healthcare and immigration to social policy. Eventually, she served in both the Chief of Staff and Counsel’s offices, making her a deeply embedded and trusted figure in the administration CBS NewsWikipediaIndependent Women's Forum.

Shaping Education and Gender Policy from the Shadows

Today, Mailman is widely acknowledged as a principal mind behind the Trump administration’s aggressive approach toward higher education institutions. Tasked with crafting policies that challenged academic freedom, diversity initiatives, and admissions practices at elite universities, she quickly became a key architect of that confrontational stance The Times of India.

Her influence extended into bold legal work as director of the Independent Women’s Law Center (IWLC). There she led advocacy defending female-only spaces, Title IX definitions, and sororities, notably serving as lead counsel in the Westenbroek v. Kappa Kappa Gamma case—a high-profile effort to uphold single-sex membership bylaws in women’s organizations Independent Women's Forum+1.

In 2025, Mailman returned to the White House as Deputy Assistant to the President and Senior Policy Strategist, becoming one of the chief architects of signature executive orders: defining “woman” in federal policy, banning gender-affirming medical procedures for minors, and protecting women’s sports. Her role also included directing investigations into Title IX violations on college campuses and pushing universities to comply with the administration’s gender policy framework Independent Women's ForumWikipedia.

Why Everyone Is Talking

May Mailman combines strategic legal brilliance with a knack for navigating policy across domains—from higher education to gender debates. Yet, she operates largely behind the scenes.

• Power Discreetly Exerted: Few outside the policy world know her name—even as her fingerprints are all over key executive decisions.

• Institutional Reach: From negotiating with universities such as Columbia to directing regulatory inquiries, Mailman has reshaped federal enforcement strategy WikipediaIndependent Women's Forum.

• Unassuming Origin, National Impact: Her arc—from rural Midwest childhood to pivotal policymaker—is a narrative of ambition grounded in real-world grit and legal acumen.