The first crisis of Jonathan Holloway’s tenure as Yale College dean had nothing to do with Halloween.

Over the course of two weeks in January 2015, a student death shook campus, a series of robberies were reported in Trumbull College and a snowstorm cancelled classes for only the second time in four decades. Just five months into his new job, Holloway was already spending much of his time resolving campus emergencies.

“I had never experienced so many things going haywire in the course of one moment,” Holloway recalled in an interview with the News. “I remember talking to some of my colleagues that had been in the Dean’s Office, in some cases for decades. And some people said, ‘This has never happened before, this is a very strange moment.’”

Holloway — who announced last week that he will step down as dean at the end of the academic year to become provost of Northwestern University — has experienced his fair share of strange moments during a tumultuous two-and-a-half-year spell at the helm of Yale College.

Last fall, he found himself at the center of campus protests over a series of racially charged controversies — one involving a now-infamous email, the other an alleged “white girls only” fraternity party — that took place over Halloween weekend.

Still, despite the crises of the last two years, Holloway has emerged with his popularity intact. Students lamented his departure on social media, and University President Peter Salovey called the news an “incalculable” loss in a communitywide email last week.

In interviews with the News, students praised Holloway for consistently listening to their concerns and moving to address them. That high level of engagement was partly enabled by recent structural changes to the dean’s role that have allowed Holloway to work with students more closely than his predecessors, giving him the chance to attend meetings of the Yale College Council and converse with undergraduates over lunch in the dining halls.

Most memorably, at the height of the protests last November, Holloway stood on Cross Campus for three hours listening to students share their feelings about the racial climate at Yale. As they reflected on his tenure, students cited the Cross Campus gathering as a perfect example of Holloway’s students-first approach to the role of dean.

“He took a lot of criticism, but I also saw him able to listen to what the community was asking for,” said Idris Mitchell ’19. “He was responsive. He really made strides and started to model the campus after what the students wanted it to be.”

A NEW JOB DESCRIPTION

Holloway arrived at Yale as a graduate student in 1989, after finishing his undergraduate work at Stanford University. He joined the University’s history faculty 10 years later and earned tenure in 2004. For nearly a decade, Holloway served as head of Calhoun College, leading the Council of the Heads of College for four years in the mid-2000s.

In 2014, Holloway succeeded Mary Miller GRD ’81 as dean of Yale College. But the job he accepted was fundamentally different from the one Miller had occupied for the previous five-and-a-half years. After Miller stepped down, the University divided the responsibilities of the deanship in two, shifting many of the academic responsibilities of the role — including oversight of tenure and promotion — to the new dean of the Faculty of Arts and Sciences position, which is currently filled by Tamar Gendler.

That structural change brought the University in line with many of its peer institutions. And crucially, it allowed the Yale College dean to focus more on undergraduate life in the years leading up to the opening of the two new residential colleges on Prospect Street.

“The job had become unmanageable the way Yale did it,” Holloway said. “It made it very difficult for the dean of the college and the dean of the graduate school to have the time they wanted to work with undergraduates and grad students.”

In an interview with the News, Miller said that during her tenure “there weren’t enough minutes in the day” for her to engage with students the way Holloway has. “I think the structural change really made it possible for him to focus on Yale College,” she added.

In addition to the structural change, Holloway has also had to manage significant turnover in the Dean’s Office and across the 12 residential colleges. In his first year and a half, Dean of Student Affairs Marichal Gentry and Dean of Undergraduate Education Joseph Gordon both left Yale. And in recent months, nine deans and heads have left their positions, most recently Davenport Head Richard Schottenfeld.

“The change was actually not just for Dean Holloway himself, but for all the moving pieces on that chessboard,” Miller said. “Just having to cover for one another, while the various searches were underway, and thinking of the new roles everyone is going to play in the college, that’s been a lot of the shift in the Holloway administration.”

His first year as dean, Holloway periodically met with students in the dining halls for informal meals known as “lunch with Dr. J.” He also attended a YCC meeting and hosted town halls and student forums devoted to pressing campus issues.

Former YCC President Michael Herbert ’16 said that before Holloway took over the YCC met with the dean only once a semester. Herbert sat down with Holloway every three weeks.

“Dean Holloway made these discussions a point of emphasis,” Herbert said. “Dean Holloway is one of the most highly esteemed members of the Yale administration, and deservedly so. I felt very fortunate to be at Yale during his term.”

Current YCC President Peter Huang ’18 described Holloway as “honest and caring,” and said he has always worked cooperatively with the YCC. Huang added that in their first meeting, Holloway vowed to help the YCC address pressing student issues.

“He told me that he would be very forthright with me and would let me know when I was being unreasonable or asking for something not quite feasible,” Huang said. “He also promised that if a policy ask was feasible and within his power, he would always work with us. To this day, he has kept his promises.”

A TOUGH JANUARY

But student leaders in Yale College — both formal representatives and members of campus advocacy groups — have not always lauded Holloway’s performance.

In January 2015, Yale’s policies on withdrawal and readmission — which govern students who leave campus for extended periods, often for mental health reasons — came under fire after a student, Luchang Wang ’17, committed suicide in San Francisco. Wang, who had withdrawn from campus earlier in her Yale career, criticized the University’s withdrawal policies in a note posted on Facebook a few hours before her death.

The same week that Wang died, Yale cancelled classes for just the second time since 1978 as the snowstorm Juno swept across the Northeast. Meanwhile, the police continued to investigate the thefts in Trumbull. On Jan. 24, the New York Times columnist Charles Blow tweeted that his son Tahj Blow ’16 — a junior in Saybrook College — had been held at gunpoint by Yale police officers, thrusting the University into the center of nationwide conversations about race and policing.

“National disasters, health crises, local tragedies — it was hard,” Holloway told the News.

And for Holloway, it only got harder.

In the aftermath of Wang’s death, students across the University began mobilizing to force changes to Yale’s mental health policies. A group of seniors threatened to boycott the annual senior class gift in protest. Wang’s friends spoke publicly about her distrust for Yale’s Mental Health and Counseling services.

At a heated town hall on Feb. 25, Herbert demanded that Holloway address the YCC’s recommendations on withdrawal policy point by point. Holloway refused, and later told the News that he would not engage in “litmus test politics.”

Moreover, the fierce debate over Yale’s mental health policy was not the only campus controversy that spring. Students also expressed concerns about the University’s protocol for addressing sexual assault allegations, as well as its management of the four cultural centers.

Still, by the end of the semester, Holloway announced major reforms to the withdrawal system — including policies designed to alleviate the financial burden of the process and make it easier for students to return to campus — that were hailed by students leaders as a substantial improvement on the old setup. Herbert told the News last week that he was impressed with Holloway’s performance during those fraught months, and that he credits the dean with important improvements to the withdrawal policy.

For his part, Holloway described the spring of 2015 as a challenging period for the University.

“And then last year came,” he added, “and I forgot all about the first year.”

THE WOMEN’S TABLE AND BEYOND

The racially charged protests that polarized campus last fall and catapulted Holloway into the national spotlight represented the culmination of years of frustration among students of color at Yale. But the immediate cause of the protests arguably boiled down to two emails — one that was sent and one that was not.

In late October, Silliman College Associate Head Erika Christakis sent an email to the college community challenging the wisdom of an administrative email effort to curb culturally insensitive Halloween costumes. Outraged students circulated a petition denouncing Christakis.

For nearly a week, Holloway did not publicly respond to the unrest. Students protesting the Christakis email — as well as an alleged “white girls only” frat party — complained that Holloway was ignoring legitimate grievances. The year before, he had circulated a campuswide email just hours after swastikas drawn in chalk were discovered on Old Campus.

On Nov. 5, 2015 — six days after the backlash to the Christakis email began — Holloway walked to Cross Campus to speak to students as they chalked messages of solidarity outside Sterling Memorial Library. Soon more than 200 undergraduates had circled around Holloway to share their pain and demand answers from the first African-American dean of Yale College.

For three hours, Holloway stood and listened, barely saying a word. Finally he stood on top of the Women’s Table and tearfully apologized to the students gathered before him.

“It is painful for me — as someone who has a vested interest in supporting you — to hear what you have just told me, but I am glad you did,” he said. “I’m here for you. I do have your back. Please know that I have heard your stories, and I’ll leave here changed.”

The Cross Campus speech — as well as subsequent closed-door meetings between administrators and leaders of a burgeoning student protest movement — helped alleviate concerns about Holloway’s response to the Halloween incidents.

Indeed, for many students, the gathering on Cross Campus has become symbolic of Holloway’s overall leadership approach: his patience, his willingness to listen and his attention to students’ everyday concerns.

“What Dr. J did on Cross Campus, just taking the time to be there, to listen, I think is really powerful, especially at this particular moment in American history,” said Andrew Samuel ’09, a Calhoun alumnus who knew Holloway. “I feel like that was emblematic of what we as a country need to learn how to do much more broadly.”

In interviews with the News, students on both sides of last year’s racial disputes said Holloway was always willing to listen to undergraduate concerns during a tense period on campus. Eli Feldman ’16 — who said he disagreed with many of the campus activists who circled Holloway on Cross Campus — said he was impressed with the dean’s leadership.

“Holloway is a very adept administrator,” Feldman said. “He’s an incredible guy. He held up very well. Especially, I think that [on Cross Campus], he really shined. I think he did an incredible job of listening.”

Abdul-Razak Zachariah ’17 — one of the students who spoke to Holloway on Cross Campus — told the News that although he was angry Holloway did not respond more quickly to the student protests, he understood the dean was in a difficult position.

“It’s hard to be an administrator of color, which is something I think he had to face without explicitly saying it,” Zachariah said. “So I definitely understood his situation, but was still critical of the fact that he couldn’t act more.”

Holloway did not enjoy the Cross Campus episode, and the campus protests took a deep personal toll. According to a profile published in The New York Times, Holloway lost five pounds in the first two weeks of November.

“It wasn’t fun to be standing there, that wasn’t fun,” he said. “But I really admire the students that when I asked to speak they wanted to listen also. That’s a credit to the community.”

Holloway said interacting with students has always been his favorite part of the job. He loved “lunch with Dr. J,” and always looks forward to move-in day and freshman assembly. In his new job at Northwestern, Holloway may have fewer opportunities for those kinds of casual interactions. But he said he hopes to teach a graduate seminar or an undergraduate course to stay connected with students.

And, he added, the administrative responsibilities of the Northwestern job appeal to him as well.

“One thing I didn’t know until I became the dean was I had a much bigger staff all of a sudden, and I discovered I really enjoyed that kind of management,” he said. “There are whole other parts of being dean of Yale College that are invisible to the public, but that I really enjoy, and there will be a lot more of that work as provost. It will be an interesting opportunity and experience.”

Asked if he might work at Yale again some day, Holloway replied, “Who knows? Let me start at Northwestern first.”

He will begin work in Evanston, Illinois, on July 1 — exactly three years after he took over the deanship of Yale College.

“It was a deep honor to serve in this job and serve students,” he said. “There are students that like what I’ve done, and students that disagree with what I’ve done, but through it all I hope students can recognize that I’m working very hard.”

Correction, Nov. 28: A previous version of this article stated that Luchang Wang ’17 posted a note on Facebook a few days before her death. In fact, she posted it a few hours before.