March 20, 2026 | By Valerie Milsop (A29)

“I do enjoy working with the students, and I think the relationship as Assistant Dean and Tutor is the ideal relationship. I certainly wouldn’t want to be an Assistant Dean if I weren’t actively engaged in teaching. The students, in addition to experiencing the problems similar to those of any student going to college, have particular problems that arise out of the program. One of these is the problem that appears when one questions one’s beliefs. And I think the students need someone to go to who can give them some foundation or can restore a little perspective and can reassure them that the world does go on, and caution them that it is not wise to question everything all at once.“

–St. John’s tutor and Assistant Dean Barbara Leonard (1916-2004), as quoted in the 1987 St. John’s College Yearbook.

Most Johnnies are probably familiar with Eva Brann, the eminent former Dean of St. John’s Annapolis and the college’s longest-serving tutor. Fewer, though, might know of our very first full-time female tutor: Barbara Leonard, who served as Assistant Dean from 1951 to 1987 and retired after having devoted 36 years to the college.

St. John’s College first accepted female students in the fall of 1951, 14 years after the New Program’s onset in 1937. This change to the previously all-male student body was somewhat contentious, but the President’s Report of September 1952 affirmed that the entering cohort of 24 women all finished out their freshman year and “seemed an unusually capable group.” With their entrance also came the invention of a new faculty position to help manage their transition: that of the “Assistant Dean for Women.” And so, the search began for an academic to fill the position.

As an alum of Oberlin College, the oldest coeducational liberal arts college in the United States, Leonard was deemed a good fit for the role. She was a visiting professor in zoology at Smith College at the time, but a lack of career advancement spurred her to drive out to Annapolis for a job interview in the spring of 1951. A few short months later, Leonard was named Assistant Dean.

Leonard, while serving as St. John's first full-time woman tutor, was not technically the first woman to become a college faculty member, as librarian Charlotte Fletcher and registrar Miriam Strange were both granted the title and fulfilled corresponding responsibilities such as attending faculty meetings and formal college ceremonies.  Nor was Leonard technically the first woman to teach at St. John’s College: journalist and author Helen Hill Miller—the wife of prominent Virginia politician Francis Pickens Miller—taught economics for a single semester in 1937. However, her position had been temporary; Leonard, whether she anticipated it or not, wound up being permanent.

The role of Assistant Dean was, at the time of Leonard's engagement, more focused on campus life, so she moved into an on-campus apartment. (Her residence lasted as long as her employment, long after all other tutors made the move to live off college grounds.) She hit the ground running, but really began flourishing in her role during her second year at the college. During that time, J. Winfree Smith, the Assistant Dean of male students, went on sabbatical. Leonard picked up the slack, serving as A.D. for the entire undergraduate population in his absence. Both male and female students continued to seek her support even after the eventual return of a dual Assistant Dean system; when the male A.D. retired, Leonard stepped up to become the sole Assistant Dean.

Leonard was actively involved with campus life throughout her time at the college. She was said to never miss a concert, and she continued to play intramural sports into her seventies. She participated in faculty plays and served on the Board of Visitors and Governors even after her retirement. Said to be gruff but in possession of a great sense of humor, many viewed Leonard as a sort of “campus godmother.” In 1980, she was celebrated as an honorary member of the Class of 1955.

Like many St. John’s tutors, Leonard—who studied the classics at Oberlin— learned from and through the New Program as she went along. From 1962 through 1963, she served as a Fulbright lecturer in the South Indian city of Madurai, during which she became the first woman to address a math colloquium of Indian graduate students and professors. Leonard, who had come to India to teach zoology, later said that most of the math on which she lectured was acquired while teaching at St. John’s.

Still, Leonard had long been a polymath in her own right, having earned an M.S. in biology and a PhD from the University of Rochester. Before joining the St. John’s faculty, she had also held various academic and research positions in science and medicine as a zoology assistant at Oberlin College; a two-time scholar at the Marine Biological Laboratory at Woods Hole, Massachusetts; and a histological technician at Yale Medical School’s Department of Pathology, where she prepared tissue samples for microscopic analysis.

This versatility is perhaps what made Leonard able to take on the St. John’s curriculum. For this, she was well-appreciated: in 1976, a surprise party was thrown to commemorate her 25th year in the role of Assistant Dean. The college bell rang 25 times, and Leonard was gifted a set of silver candlesticks and an engraved silver tray.

Leonard’s retirement was similarly celebrated with a collegewide party in 1986. Held on her 70th birthday, the Continuum Chamber Singers of Washington fêted her with a rendition of “Happy Birthday,” and the retired tutor reportedly received a standing ovation from all present. The following spring, she delivered that year’s commencement speech before retiring to her birthplace of Oberlin, Ohio, to live with her sister and sit in on classes at her alma mater.

Barbara Leonard—also known to some as “Barbara the Great,” a title bequeathed to her at her 25^th college anniversary celebration—passed away in 2004 at age 87. But her legacy lives on: many of her donated books can still be found among the collection of Annapolis’ own Greenfield Library. The next time you flip through a borrowed title, keep an eye out for her name on the interior cover.

This article first appeared in the Gadfly, St. John’s College’s student newspaper. It has been lightly edited for style and clarity.