This piece originally ran on January 24, 2004. It was announced in January 2025 that
May Mailman will again work under Trump in his second stint in the White House.

In 2017, May Mailman (nee Davis) got an out-of-the-blue call asking if she wanted to work in
the White House for then-President-elect, Donald Trump. Days later she had packed up and
moved from Denver, where she served as clerk on the Tenth Circuit Court of Appeals, and had
relocated to Washington, D.C.

Mailman put in long hours in the Staff Secretary office, which is responsible for paper flow in
the White House, she said. Any time the president needed to sign something, if a press release
was coming out, anything on paper went through that office.

“It’s a very small office and requires a lot of attention to detail; it’s a tremendous amount of
work.”

So much work that in her first few weeks in D.C., Mailman couldn’t even get to a grocery store.
“I was never able to leave work when a grocery store was open. I ordered Cliff Bars from
Amazon so I would at least have something to eat.” Adding that D.C. operates on more typical
hours than New York City or L.A.

Mailman added that she “has always been conservative” but wasn’t political online, which
allowed her to be hired. A friend in the White House passed along her name, and thus the cold
call that offered a presidential gig.

“It was a little bit of luck but a little bit of connections; you have to have your friends in the
right spot,” she said.

She stayed at the White House for the entire Trump term, also serving in a communication/facilitator role she helped create, and in the White House Council Office, a role she took on just before COVID.

“It was a wild amount of legal questions: ‘Can you mandate masks on an airplane?’ ‘Can we
shut down the cruise industry?’ ‘Can we import masks that are not FDA approved,’ immigration
stuff, flights from Europe. It was a crazy amount of questions,” she said.

Being a lawyer had always been a goal, dating back to her time at CCCHS, from which she
graduated in 2006.

“We did a mock trial about Huckleberry Finn and that really spoke to me,” she said. Adding that
her former teacher recently told her about her incredible gumption for law, even as a teen.
“I have no recollection of this,” Mailman laughed. “But apparently I emailed a Harvard
professor and asked him to help with the case, which is so absurd.”

The professor helped, and after getting her bachelor’s degree at KU, Mailman herself attended
Harvard for her law degree. (Though she never took that particular professor’s class.)
Being from a small town may make it harder to get a high-profile job, Mailman said, but not
impossible.

“You really do have to know someone to get the job. But it shouldn’t be discouraging because
you can go make those connections. It’s harder [in a small town] but it’s possible.”
After the Trump administration lost the election, it meant Mailman was out of a job. Three days
later she went on a blind date with her now-husband and weeks later she was moving to
Cleveland.

These fast-paced career changes, however, are par for the course when working in politics, she
said. And with no more connections in D.C., it made sense for her to move.

In Cleveland, Mailman took another career shift and worked as the Deputy Solicitor General for
the State of Ohio two years, before settling into the nonprofit sector. Today she works with the
Independent Women’s Forum, which is the “leading national women’s organization” on female
protections and freedoms.

She works on cases that affect sororities, women’s prisons, definitions of gender identification
and legality within the NCAA, and more. She often works with various states, or at a national
level.

“The big push right now is women’s spaces and women’s sports. It’s a lot of litigation,” she said.
She has also appeared on several talk shows – in person or from home – where she is asked to
provide legal context and information on various issues.

Not only does this align with her personal goals, it also makes more sense logistically. She also
has a 1-year-old daughter with another on the way.

“It’s a group of women who agree with me on issues, agree with me on how to go about
tackling those issues and the ability to have enough flexibility to take care of your family. It’s
the perfect situation,” she said.

Adding, “If you’re going to spend time away from your baby, it needs to be something you’re
very passionate about. And I love working on these issues; I could do this forever.”