And he was shuttling from one meeting to the next, as Yale’s administrators weighed the latest demands from protesters, including requiring that all undergraduates take an ethnic studies class, the hiring of mental health service providers for the cultural centers geared to minority students, and the renaming of Calhoun College, which honors John C. Calhoun, the 19th-century American statesman, who was an ardent defender of slavery and a white supremacist.

All the while, the dean was reflecting on the challenges of reconciling his sometimes dueling roles, as an administrator, a professor and a popular sounding board for students.

Dr. Holloway, who earned his doctorate in history from Yale in 1995, has spent 16 years on the faculty and wears a navy blue Yale tie to the office most days. (He keeps six Yale ties in his closet on regular rotation.) He is, in many respects, a quintessential Ivy League insider. “A team player,” he said, describing himself.

But as an African-American and a scholar of black protest movements, he is also intimately familiar with the sense of marginalization experienced by some students, who have described being subjected to racial slurs, casual insults and tone-deaf comments from classmates and faculty members.

“Their pain was pain I recognize; I didn’t need to have a translator to understand that,” Dr. Holloway said. “Not only do I live life on this planet as a black man, I teach the civil rights era. It’s what I do.”

Even so, some students complained that the dean had become disconnected from their problems.

When black students initially invited Dr. Holloway to meetings about their concerns, he sent representatives from his staff. (He said he had longstanding commitments, including giving a talk at the New Haven Public Library on a new edition of W.E.B. DuBois’s classic, “The Souls of Black Folk.”)

“They didn’t respond as quickly as they should have,” said Jay Gitlin, a lecturer at Yale who teaches courses on American Indian history and the American West.