Brianna Loo

Before he became the first African-American dean of Yale College, Jonathan Holloway was simply “Dr. J” — the beloved head of Calhoun College.

During his nearly decadelong tenure at Calhoun, Holloway, who announced in an email last week that he will step down as Yale College dean at the end of the academic year, faced many of the same challenges that have defined his tumultuous two-and-half-year deanship: campus tragedies, racially charged symbolism and the everyday demands of student engagement.

In interviews with the News, former students said Holloway, who served as head of the college from 2005 to 2014, commanded the respect and admiration of the community as he fulfilled every aspect of the job, from mentoring undergraduates to sending stern emails about bathroom hygiene.

“I very powerfully remember Dr. J representing everything that was good in the University — intelligent and articulate and poised, but not in a way that seemed distant at all,” said Sara Samuel ’15, who worked as a college aide under Holloway. “He seemed approachable. It’s only in the years since then that I’ve really come to appreciate how difficult that balance could be.”

Holloway, a history and African American Studies professor, never expected to become head of Calhoun when he joined Yale’s faculty in 1999. After earning tenure in 2004, he took a year off from teaching and was conducing research in California when he received a phone call from then-University President Richard Levin.

“I actually thought it was about becoming the next chair of African American Studies, but immediately it was an invitation to serve as the head of the college,” Holloway recalled. “That just came out of the blue, a complete shock. I guess President Levin saw something in me that he thought could translate well.”

Holloway was quick to accept the Calhoun post: He and his wife Aisling Colon liked the idea of surrounding their daughter Emerson with strong, intelligent young women. After arriving to Calhoun in 2005, Holloway made an effort to engage closely with students: He attended college council meetings and invited community members into his home for candy on Halloween. When he went on sabbatical in 2012, students brought a life-size cutout of Holloway to Calhoun events.

But the fun-loving Dr. J, known for joining students on the dance floor at college events, had a disciplinary streak as well. Alumni also remember him as “Crazy Uncle Johnny,” the fiery persona that emerged when students were caught smoking marijuana or breaking beer bottles in the courtyard.

After one of the Calhoun bathrooms flooded in January 2007, Holloway penned a now-legendary email, imploring students to stop having sex in the college showers.

“Several times since the start of the spring term some Hounies have come across a couple having the time of their lives in a shower stall,” he wrote. “Such continued brazen public displays of affection will only invite public embarrassment. I beg of you, let’s not go there.”

Later that year, Leslie Woodard, a member of the English Department who was also black, joined Holloway as college dean. By all accounts, Woodard and Holloway, who were close friends, formed a formidable administrative partnership.

“I know people who had a choice of colleges and basically chose Calhoun because of Dean Woodard and Dr. J,” said Sasha Frankel ’16, another former college aide. “It was a powerful combination of people and personalities to have in charge, and they were both really outstanding people.”

According to former Calhoun aide Austin Bryniarski ’16, Holloway and Woodard appreciated the “tinge of irony” in having two black administrators at the helm of a college named for infamous slavery supporter John C. Calhoun, class of 1804. When she marched in the annual commencement parade, Woodard brought along a walking stick originally owned by the college’s notorious namesake, Bryniarski said.

In October 2013, Woodard died suddenly and unexpectedly in her home in Calhoun. She was 53 years old. Holloway — who had already announced he was leaving the college at the end of the academic year — was tasked with uniting the college in the wake of a horrifying tragedy.

“What I had to do in that moment was, as much as I possibly could, put aside my most personal feelings and be there for everybody else,” Holloway said. “That was very hard to do. You have a job — you have to do the job.”

Fighting back tears at a candlelight vigil in Calhoun, Holloway called on students to remember the values Woodard worked to instill in the college community.

“I’ll never forget standing in a circle holding a candle in the Calhoun courtyard, and hearing Dr. J both break down with sadness, but also recite a phrase that Dean Woodard often said: ‘Pick yourself up, dust yourself off and march,’” said Jacob Wolf-Sorokin ’16, another former college aide. “That moment embodies this dualism — both of how we move forward and yet how he really could engage on a human level as well.”

Holloway will leave Yale to become provost of Northwestern University in July. In recent weeks, he has found himself guiding students through another traumatic period on campus: three student deaths and a polarizing presidential election, all in the wake of the racially charged protests that swept the University last year.

“I really loved working with the students and watching them grow and change over the course of their time,” Holloway said. “I discovered over the course of my tenure that the head of the college could actually make a really positive role in the community and really set the tone of the community. That was one of the lovely surprises of serving as master.”

For many of Holloway’s old students, the intimacy of his stewardship stands out as an essential aspect of their Calhoun experience.

The weekend before Thanksgiving, Wolf-Sorokin joined several of his friends from Calhoun to see Yale’s football team beat Harvard 21–14 in Cambridge. Holloway — a former outside linebacker at Stanford — was also in town for the latest edition of The Game.

“My friends and I were down there on the field celebrating after Yale won and looked up into the stands, and who was there but Dr. J,” Wolf-Sorokin recalled. “We made eye contact, and gave him a big smile. He was beaming right back.”