From Kentucky to Cambridge, Overseer Candidate Trey Grayson Says Pragmatism Key to Harvard-Trump Standoff

Board of Overseers candidate Trey Grayson ’94 said he would be open to a potential settlement with the Trump administration if elected in May, arguing that Harvard should remain pragmatic as it navigates mounting federal pressure.

Grayson, a Republican and former Kentucky Secretary of State, is one of nine candidates endorsed by the Harvard Alumni Association for Harvard’s second highest governing body. The top six vote-getters will join the board in July.

Grayson, currently a partner at law firm Frost Brown Todd Gibbons, said Harvard should at least consider striking a deal to avoid further retaliation and resolve a situation that is “occupying a lot of bandwidth” for the University.

“You have to say you’d be open to a settlement,” Grayson said. “The reality is this administration is going to be there for another three years.”

“Of course, you’d have a lot of questions about it, but I just think it's not responsible to say, ‘Oh, I would never make a deal with the administration,’ just given how much is at risk,” he added.

Grayson said his interest in the role grew out of both loyalty to the University and concern about the moment it faces.

“It’s a really critical time at the University — there’s a lot of pressures coming from a bunch of different directions,” Grayson said. “I think there’s some serious conversations that have to take place. I don’t have the answers to all that. I think it’s really important to engage that conversation.”

A Kentucky native who attended Harvard in the early 1990s before returning to public service in his home state, Grayson said his background gives him a perspective often missing from Harvard’s leadership. He currently lives in a deeply Republican area and said many of his neighbours are skeptical of elite higher education.

“Being able to have a pretty good understanding as an insider from that time on campus, but also, as a bit of an outsider coming from a part of America where usually there's not as much representation on the Board of Overseers — I think it’s an interesting dynamic,” Grayson said.

Grayson has previously held leadership roles at Harvard. He served as director of the Institute of Politics from 2011 to 2014 after an unsuccessful bid for U.S. Senate. As a student, he was the vice chair of the IOP’s Student Advisory Committee and chaired the Kirkland House Committee.

Friends from his time at Harvard said Grayson was always open about his roots. Elizabeth R. Caputo ’94, a longtime friend who chaired the IOP’s Student Advisory Committee during Grayson’s tenure, recalled that he frequently wore University of Kentucky basketball shirts.

David V. Bonfili ’96, another classmate who served on the IOP, said Grayson stood out among peers who left for finance jobs and major cities after graduation, dead set on returning to public service in Kentucky.

“I thought that was a great example of someone who grew up in Kentucky, had the experience of being at Harvard for four years, and then went back to contribute at home,” Bonfili said.

Whoever is elected to the Board of Overseers will take office amid Harvard’s ongoing standoff with the Trump administration, which has intensified in recent weeks and is expected to shape the board’s agenda.

In recent weeks, the administration has expanded its pressure campaign: the Department of Defense severed academic ties with Harvard, and days later, the Department of Justice sued the University over its refusal to provide admissions records tied to a federal investigation.

Grayson said his own experience at Harvard shaped his support for diversity in higher education, though he acknowledged the political challenges surrounding the issue.

“Diversity is something that was an attraction to me,” Grayson said. “That’s a core value for the school. But how do you navigate that post-the Supreme Court case?”

In response to the ruling, Harvard has implemented internal reforms aimed at limiting federal security, including barring alumni interviewers from mentioning race in written reports.

Grayson, who has interviewed applicants since graduating in 1994, said the change was “tricky” to navigate and that it “feels a little weird.”

“We’re not allowed to ask certain questions or write certain things down, and I know as a campus, we’re kind of struggling with, ‘what does that all mean?’” Grayson said.

But Grayson confidently backed other changes under Harvard President Alan M. Garber ’76, including Harvard’s 2024 move toward institutional neutrality, under which it refrains from taking official positions on political issues.

“That was a good move. Because as soon as you start weighing in, then you have to decide,” Grayson said. “I was really glad the University moved to that. I think that’ll pay dividends in the future.”

Botany professor Donald H. Pfister, who served as Kirkland Faculty Dean while Grayson chaired the Kirkland House Committee, called Grayson a “very special person” with an ability to work constructively across differences.

“He thought about how he could be inclusive — listening to different views and coming to common agreements,” Pfister wrote in a statement. “He impressed me as being a very kind and generous voice.”

—Staff writer Elise A. Spenner can be reached at [email protected] or on Signal at elisespenner.82. Follow her on X @EliseSpenner.