End of an Era: Head of School Barbara Riley Retires from Life on The Hill After 20 Years

Riley’s initial approach to the position was based on her belief at that point that her role was only temporary. “It was interesting for me at that age because I had never planned or prepared for leading a school, and there was a certain freedom that came with knowing I would only be doing it for a year,” she explained. “My real job is to use my judgement, and I started to develop a foundational philosophy of what the job was about, but without the fear of making mistakes that I might have had if I thought it were permanent.” 

After a failed search for a new Head over the 2001-2002 school year, the Board of Trustees asked Riley to stay on for the second year as an Interim, but by the spring of 2002, Riley was asked to stay on as the permanent Head of School. “I was really excited to keep doing it,” she said. “All of my academic life I’d been a specialist in 19th century literature or 20th century public policy. I went from being a specialist to being a total generalist who needed to understand endowments and budgets and employment policies, and work with a lot of different constituencies: students, parents, alums. It was really exciting to be learning on so many levels.”

Though her first big project was to bring the school’s daily schedule to its current form, much of Riley’s work over the course of her tenure as Head of School focused on improving infrastructure on The Hill. The Hopkins campus has changed enormously since Riley took office in 2001; over the course of those fifteen years, Riley and her Construction Committee have renovated Calarco Library and built Heath Commons and Thompson Hall. Athletics was bolstered by a number of significant projects. The school rebuilt all of the tennis courts, created the new soccer/lax and boys’ baseball fields, the Smilow Field for girls’ field hockey and lax,  the Kneisel Squash Center, and the Parr Field. “You sit down and you start to decide what you’re trying to accomplish with this building. In a lot of ways, the function determines the design,” Riley explained. “They were all so much fun, because they were all about putting better roofs over people’s heads.”

One of Riley’s last efforts as Head of School was the Conversations on Race program that the Hopkins community undertook this past school year. In a community-wide email sent out in September, Riley described the program as an initiative to “engage our community in a conversation about race and racial identity… and to individually and as a community confront the unease, the habits, the unconscious biases that at best inhibit, but more often preclude, the conversations that can take us to greater self-awareness and understanding of others.” The Program has been met with both criticism and praise; one of the most controversial efforts came in the form of three affinity-based student dinners that Riley hosted at her house. Looking back on the Program, Riley said: “We learned about how best to talk to each other. We do our best thinking and growing when we stay home-grown. Your best conversations actually took place outside of the conversations we organized on campus. The day Edens [Fleurizard ’16] told his story in Assembly was the most moving, true, best moment in the whole year for all of us.”

While Riley is proud of everything she has accomplished as Head of School, she must also accept the fact that she could not accomplish everything she might have hoped to. “When you come to the end of your time in a place, you think about all the things that are still on your to-do list,” she said. “That we are not ready to commit to a Performing Arts Center is a huge regret for me.” She also wishes that she could have led an effort to create a boarding facility at Hopkins to accommodate the needs of those students who travel from far away, and acknowledges that while huge strides have been made in terms of financial aid packages, there is still much more work to do. 

On a more personal level, Riley’s absence from the classroom as Head of School remained a source of regret for her throughout her tenure. “I made a decision that first year not to teach because I was afraid I would be unreliable. I never went back to teaching and I always missed it,” she admitted. “The greatest privilege and thrill of being at a school is being in the classroom.” 

When Riley formally ends her tenure on June 30, she will hand the reins over to Kai Bynum, who will join Hopkins from Roxbury Latin School in Massachusetts, where he served as the Director of Studies and Director of Academic and Strategic Initiatives. Riley is effusive in her praise of Bynum: “He is so perfectly suited to this work and to take over this school. I hadn’t realized I was apprehensive about who the next person could be until I knew it was Kai and I was so happy.” Her advice to Bynum has been to “stay as involved with all the dimensions of school life has possible.”  

Riley remains uncertain about the exact nature of her future, though she has a whole host of things that she might like to pursue: “I think about mentoring other heads, I think about scholarly writing, I think about foundation work. But mostly, the best advice I’ve been given is to not jump into anything and to really think about where I want to be about next,” she said. “So I don’t know what’s next. The one-word answer is ‘something.’” 

In the meantime, Riley has purchased a house in Guilford, Connecticut, where she raised her children and lived for twenty years. Though it was widely expected that she would move to Los Angeles, where her three children live, Riley knew that she wanted to take some time for herself before moving into her children’s world. “I’m temperamentally unsuited to becoming an Angelina,” she joked, adding, “I needed a project this year that would help me move away, so I bought a house in Guilford last August, and I’ve been moving emotionally and physically into a new space.”

Over the course of her time at Hopkins, Riley has worked closely with countless students, faculty, and administrators. Assistant Head of School John Roberts, who worked alongside Riley for 13 years, said: “She is arguably among, if not the, most influential and successful Head of Schools in Hopkins history.” English teacher Donna Fasano, who has seen five Heads of School come and go during her four decades on The Hill, said, “While change in the Head of School is an inevitable part of my long lens on Hopkins history, I have enjoyed the stability of Mrs. Riley’s tenure and am grateful that she has been my boss for a significant part of my career. I will miss her!”

When Riley’s time as Head of School comes to an end, she will be remembered as a lover of history and To Kill A Mockingbird, as a “House of Cards” megafan and a Ski Lodge cookie benefactor extraordinaire, but, most importantly, as someone who contributed immeasurably to the community here on The Hill.