The master of Yale College

It didn’t take Jonathan Holloway, GRD ’95, long to realize that he didn’t quite fit into his new office. All he had to do was take a seat. “The desk and chair had been set for my predecessor, who’s not my size,” Holloway, a former outside linebacker for the Stanford University football team, told me. “I don’t fit comfortably under the desk.”

Besides this slight discomfort, his physical office, located in SSS, is quite striking—its dark wood floors, large windows, fireplace, and tasteful decor (works of art from Yale’s vast collection) create exactly the environment that one might expect to find in the office of the person who runs one of the world’s most prestigious undergraduate institutions. A new desk is scheduled to arrive sometime in the next couple of weeks.

The undersized desk and chair physically embody Holloway’s experience over his first few weeks, as he works through the changes inherent in his new position. When I asked how things are going so far, Holloway responded: “I think it’s going well.” In reflection, he noted that the most notable change for him so far has been that for the first time in eight years he’s no longer thinking like the master of one residential college. Now, at the helm of the entirety of Yale College, the scope of his perspective extends well beyond the Calhoun College courtyard. “For residential college masters and deans, the opening week is one of intense anxiety because you just want people to be safe, and I still want people to be safe, of course,” he said, “but I didn’t fully realize the extent to which things have to be uniquely bad to rise up to my attention. Thank goodness nothing truly scary has happened, at least to my knowledge.”

By his own account, then, this first week of classes has gone well for the new dean who himself represents many important firsts for Yale College: he is the first African American dean of the college; the first to choose to fully live on campus in more than a decade; and the first big appointment of President Peter Salovey’s, GRD ’86, administration. With all this in mind, perhaps the most significant first Holloway represents is that he’s the first dean to take on this position alongside a Faculty of Arts and Sciences (FAS) Dean—held by Tamar Gendler—a new position that will radically alter the responsibilities of the Deans of both Yale College and the Graduate School of Arts and Sciences.

The dean’s role has changed dramatically, and Holloway, with his track record of leadership and achievement, will be the first to take it for a spin.


“An inevitable decision—the only decision— because he has so many qualities that make him a great dean,” says Elizabeth Alexander, Thomas E. Donnelley professor of African American studies and professor of American Studies and English, regarding Holloway’s appointment. While to some degree this glowing review certainly presents a bias from a longtime friend and coworker, Holloway’s resume and accomplishments up until now point towards its accuracy. Since his arrival at Yale as a professor in 1999, these “qualities” that Alexander refers to have led him into leadership positions in every role he’s held. He was granted tenure in 2004, rising to the chair of the African American Studies Department in 2013. He was appointed Master of Calhoun College in 2005 only to become chair of Council of Masters just four years later. Now, after just 15 years as a Yale professor, he finds himself atop Yale College.

These qualities, his mentors and friends say, have been consistent about him from the time he started working towards his PhD. “If you met him 25 years ago or if you met him today, you’d see that he’s incredibly thoughtful, a good listener, he enjoys being with people, and he enjoys his family and friends,” says Raul Ramos, GRD ’99, a scholar of U.S. western and chicano history at the University of Houston, who was a classmate of Holloway’s at Yale. Jon Butler, the head of Yale’s history department when Holloway was a student similarly notes his empathetic qualities. “He understands that with all of the issues in the world, it’s people who can make a difference. He has a deep understanding that the things that academics do— analytically, conceptually—boils down to simple questions: can you do it? And can I do it? Can a teacher help someone realize that capacity in themselves?”

Butler, who recalls hearing about Holloway from a friend of his at UCLA before he started at Yale, met Holloway during Holloway’s first few weeks on campus. “My early impressions of him are very similar to my continuing impressions of him. Jonathan was really smart. Very eager. Very serious. He had something to accomplish in the world. He wanted to be a historian.” Ramos remembers a softer, doughier side to Holloway during these years: “He is a connoisseur of fried dough: we made many late night donut runs, and he savored every bite.”

After completing his PhD, Holloway went on to teach at University of California, San Diego in its ethnic studies program—a top program in its disincline—until returning to Yale just four years later in 1999. Butler, who was the chair of the History department in 2004 when Holloway was up to receive tenure, notes how impressed everyone was with Holloway. He recalled that in the old tenure process that Holloway went through, it was a requirement to conduct a national search to fill any position. “You had to start all over again and do a national search and bring candidates in, and Jonathan was one of those candidates,” he recalled. “And he just wowed everybody. He was better than anyone we brought in. We brought really well recognized, tenured people from prestigious academic institutions, and he was better than they were.”

It is worth noting that Holloway comes from a family of high achievers. His grandfather, William Trent, was one of the founders of the United Negro College Fund. His father had a long career in the armed services until he began working as a lobbyist in Washington, D.C. His brother, Brian Holloway, was an all-pro lineman for the New England Patriots and the LA Raiders in the National Football League. His uncle, Barrington Parker, ES ’65, LAW ’69, is a federal judge and a member of the Yale Corporation.

After becoming the Master of Calhoun College in 2005, students began affectionately calling him “Dr. J.” Holloway would commonly be seen with his wife Aisling Colon, who serves as the director of Yale’s residential college seminar program, and kids, Emerson (named for Ralph Waldo Emerson) and Ellison (named for Ralph Ellison), in the Calhoun dining hall. “As Master, Dr. J. brilliantly toed the line between a social presence, role model, and authority figure,” Sara Samuel, CC ’15, president of the Calhoun College Council and one of the four students on the committee that chose Holloway’s replacement. Samuel also notes that it’s generally known that you want to stay on his good side, or else you’d hear from “Crazy Uncle Johnny”—an alter ego created by Hounies to embody the imagined writer of his strongly worded disciplinary emails. “He has an ability to elevate these emails to an art form,” Samuel says.

Emails aside, his work in Calhoun perhaps best showcased his strengths. “He’s a firm believer in treating everyone the same and with respect, which sounds like a lot of platitudes, but it’s all true,” notes Sheila Enamandram, CC ’13, a former Calhoun College Froco. “He has a considerable ability to form a community, which makes me excited to see him in his new role.” It is this ability that will most be tested given the changes to the structure of his role.


On Fri., Jan. 24, President Salovey emailed the Yale community to announce that both Yale College Dean Mary Miller, and Graduate School of Arts and Sciences Dean Tom Pollard would be stepping down on Mon., Jun. 30. In the email, Salovey told students and faculty that he would establish a 14-member search committee to fill these roles, with one of these seats dedicated to a current Yale College student, which was left to the YCC to fill in whatever way it saw fit.

At the YCC meeting on Sat., Feb. 22, where the student position was discussed, “there was a very contentious debate about how the YCC would appoint the student representative,” according to Scott Stern, BR ’15, who attended the meeting. One of the options—the one he, among others advocated for—was to have an open election among the entire student body to choose the representative. “After a contentious debate, the YCC decided that they were going to choose this person themselves.” Last year’s YCC president, Danny Avraham, BR ’15, was that person. In an email to the Herald, Avraham said that the YCC funneled student input from a broad section of Yale directly to the committee through online forms, town hall meetings, office hours, and direct outreach to several student groups and cultural houses.

The content of the debate aside, the implications of Stern’s suggestion to openly elect the representative are worth noting: Take a second to imagine if there indeed was an election and you got to sit in what ultimately turned out to be Avraham’s position—what qualities, accomplishments, and academic discipline among a whole host of other factors would you weigh to render a recommendation to the committee?

The committee was tasked with compiling a list of candidates to fill any one of the three open roles, without the exact responsibilities of the FAS Dean’s position clearly defined. Thomas Appelquist, the Eugene Higgins Professor of Physics who has previous served as the dean of the Graduate School of Arts and Sciences and a search committee member, says that the committee was tasked to create a general list of people from which to source the open positions. “For instance, for the dean of the college, there’s a whole set of issues that have to do with the curriculum and how the students are best served. At the same time this person plays some role in developing the faculty, but that aspect was going to change in a way that was still being scoped out.”

Since revising the tenure process over almost a decade ago, the dean of the college had the dual responsibility of making decisions regarding the undergraduate experience, and decisions pertaining to developing Yale’s faculty. Gendler, who is the inaugural FAS Dean, notes that the Yale College Dean and the dean of the graduate school used to have responsibilities that pertained heavily to promotion and tenure decisions. “Both deans of the college and the graduate school spent probably 300 hours of their year preparing for and attending such meetings,” she says.

When asked why he and University Provost Ben Pollack decided to create the position, Salovey wrote in an email to the Herald that he was following the findings of a faculty report, entitled “Report Of The Ad Hoc Committee On Decanal Structures,” that suggested that they do so.

The creation of the FAS Dean position could be seen as a restriction or reduction of the scope of the Yale College Dean, but this view sees the glass as half empty, not half full. As it’s defined under the new arrangement, the Dean of Yale College is now free to more fully devote attention to the needs and development of all student issues—curricular and relating to life on campus—of Yale College.

As the document also notes, the Dean plays an important role in representing the University to the rest of the world. By and large, Yale has a stellar reputation globally as a humanities institution, with a weaker reputation in STEM fields. But in recent years, the university has made a push to develop more in this direction, and so it would seem reasonable to assume that the institution might appoint a hard scientist as its dean. Holloway, conversely, was promoted from within a department in the humanities.

Appelquist, a professor from the hard sciences, noted that beyond the surface level, this concern is invalid. However, Holloway’s academic background does mean that he’s had a singular exposure to humanities departments, which might make him somewhat unaware of the unique circumstances and cultures of departments in the hard sciences: “I served as dean of the graduate school in the 1990s, and it gave me a good look at the interesting differences between different departments and different areas,” Appelquist says. “[Holloway] came out of history, so some of the areas might be a bit more of a challenge—he’ll have some learning to do, and other areas will look unfamiliar to him.”

Still, Gendler notes that a similar lack of general perspective is going to happen regardless of who is tapped for a position with as broad a reach of administrative oversight as the dean of Yale College. “I think he will be profoundly effective as a result of the kind of academic training he has received in the humanities,” Gendler says. “Of course, that means that he’s less personally connected to the physical and biological sciences… but anybody that’s in a leadership position in the University comes from one or the other of the disciplines.”

As dean, the impact of Holloway’s educational background might be felt in his role most notably in a very different way: Holloway, a career teacher, will now spend his time running the college, not instructing in its classrooms or creating new works of scholarship to fill its syllabi. Specifically, Holloway is a scholar of post-emancipation American history. His first big book, Confronting the Veil, chronicles three young black activists who criticized the NAACP for its tempered civil rights agenda. His second big work, which was published late last year, titled Jim Crow Wisdom: Memory & Identity in Black America Since 1940, has been met with major scholarly acclaim, winning 2014 American Book Award. In it, he examines his own familial history and lived experiences against the broader social history of race relations in the United States over the past 70 years. Alexander predicts that this work will likely be recognized for its formal innovations. “Part of what’s so important is that the family stories and first person ventures show us that to really understand the sometimes unspoken history, you can’t understand it unless you have the first person. It’s a wonderful book.”

In the classroom, Holloway’s work has been equally as notable. His most broadly taken course “African American History: From Emancipation To The Present,” which he most recently taught in spring 2014, has a stellar reputation among undergraduates, with an overwhelming number of “excellent” ratings in its evaluations. “The extent to which he knows the students, in listening to him talk about them, their dreams, and aspirations—he loves Yale undergraduates, and that’s why he’s achieved that rare combination, both in Calhoun and in our department, as someone who is both respected and loved,” Alexander says.

When I asked whether he was planning to teach during his deanship, Holloway winced. He shared that before he had heard about his appointment, he had already decided that he and his family would move from the residential college and back into his own home in Cheshire, Conn. His near-decade calling a residential college home would be over. “I had made peace with being an educator,” he says. However, when this opportunity arose, he saw it as a chance to deeply shape Yale’s undergraduate experience on a much larger scale than he had ever had as Master of Calhoun.

Nancy Wiess Malkilel, a longtime friend of Holloway’s and a former dean of Princeton College, notes his move towards administrative positions. “There are some people who are just really good at understanding how institutions work, and at seeing possibilities for making connections to enhance the educational process,” she said. Holloway also shared that he has a love for management. “This job has a much larger staff below me than I had in Calhoun, and affords me the chance to make decisions at a larger scale than I had before,” he shared.

“He’s had an enormously interesting time, and really rewarded personally to do something about education in a scope broader than what we do as scholars and teachers,” says Malkilel.

However, given the way that his role as dean is currently defined, he hopes to return to the classroom, and soon. While he shared that Dean Miller and president Salovey, who had served as dean before Miller, both advised him not to teach this academic year, as he would still be feeling out his new role, he’s eyeing a return to the classroom next year. “I plan on teaching in the 2015-16 school year in some form.”


Walk up Prospect Street, past the site where Yale broke ground on the new residential colleges last fall, and past the Whale where the Yale hockey team plays its home games, and you just might run into the Holloway family, finalizing their move into the Dean’s Residence at 202 Prospect Street.

“I really like the idea of a dean living on campus, in the sense that, especially in the way they’ve restructured the job, there are real opportunities for the dean of the college to interact with the students in a way that previous deans simply couldn’t, given the nature of the job before,” Holloway—who will be the first dean to live on campus full-time in the past decade—says. “So it seems to me that given this opportunity, it would be great to take advantage of it. So, I’m looking forward to actually sitting down and getting to know students.”

And he is already taking the chance to do this—he has reached out to all Yale undergrads with his “Lunch with Dr. J. Program,” which will allow groups of 12 students to share lunch with Holloway over the course of the year—and he has generally been open to students reaching out to get to know him. “In his introduction in the freshman assembly, he was introduced as a lover of board games, namely Boggle,” Brandon Marks, BR ’18, recalls. Marks and his suitemates have recently been playing the board game Settlers of Catan, and he reached out to see if Holloway wanted in. “I didn’t think he’d respond,” he said. “But he did, saying that he didn’t know how to play the game, but that he wanted to learn, and more generally, have a game night at his house.”

Holloway’s closest undergraduate neighbors, just across the street, will eventually be the 800 future dweller of the new, presently unnamed residential colleges. In his email on Weds., May 21, announcing the dean appointments, Salovey stated that the dean of the College will have a “key role” in developing the two new residential colleges. Having already sat on committees that pertain to the conception and development of these colleges, Holloway is already deeply immersed in the issues pertaining to the expansion. “Some things are nuts and bolts. We have to figure out when we’re going to name our masters, when we’re going to name our deans. That’s straightforward,” he says. At the same time, he said he’s dealing with decisions that are decidedly more complex, some of which lead to broader strategic questions for the entire college. “Advising in the colleges—we are growing by 800 students, but we’re not growing the faculty. Advising now needs lots of help, we all recognize that. How are we going to actually change advising at Yale? That’s a big one, and now’s the chance to do it.”

Ultimately, Holloway envisions his role as dean in the same way that many around him see Holloway the man—an earnest ambassador for the students of Yale College. In fact, the way that the deanship is defined demands exactly that. Now it’s up to Holloway.


Illustration by Zachary Schiller and Julia Kittle-Kamp

CORRECTION: Due to an error on the part of the editorial board, an earlier version of this article incorrectly suggested that Dean Miller had not been present at Yale College extracurricular events as a result of the manifold duties of the office of the Dean of Yale College.

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