A 1975 graduate of Washington College, Bryan Matthews knows nearly every corner of his alma mater. Over more than 25 years he has served in athletics, admissions, student affairs, and now in the president’s office, he is guiding the institution through some challenging times.

When Matthews stepped into the interim presidency in mid-August, Washington College was in what he calls “a financially challenging situation, to put it mildly.” Since then, he and his cabinet have carried forward former President Sosulski’s  steps to bring the budget back into balance. “Positions were cut, expenses reduced, and a zero-based budgeting process was installed,” he said. “We’re now in a manageable position. It doesn’t mean everything’s great—but it’s stable.”

Enrollment trends have also turned slightly upward. The incoming freshman class exceeded budget projections and improved net tuition revenue, providing what Matthews described as “a modest but meaningful boost.” The college still faces a small shortfall this year, but the focus now, he said, is on increasing revenue through enrollment growth and retention. “That’s where my history as a coach and recruiter serves me well,” he said. “I like it, I understand it, and I see it as our best opportunity for sustainable growth.”

Matthews is quick to emphasize that faculty programs were protected during the cuts. “No faculty were let go, and no academic programs were dropped,” he said. Most of the expense reductions came from staff attrition and voluntary retirements. “This is the first semester that people are flying the airplane with a smaller crew,” he added. “There’s strain, but there’s also remarkable determination.”

Returning to the College after a decade away, Matthews has been struck by how teaching and learning have evolved. “Ten years ago, classroom technology was clunky. Now it’s seamless—it drives the conversation instead of interrupting it,” he said. “Our faculty have really embraced experiential learning, no matter the discipline.” He shared the story of a junior chemistry major who spent last summer doing graduate-level research at Montana State University. “That’s the level of preparation happening here,” he said proudly.

Matthews’s listening tour during his first eight weeks brought him face-to-face with every academic and staff department. What he found, he said, was a community that had weathered hard years but remained resilient. “Crisis brings people together. We may not agree on everything, but we’re aligned—we want to succeed and thrive.”

He sees that same interdependence extending beyond the campus. “What would Washington College be without a successful Chestertown, and what is Chestertown without a thriving college?” he asked.

His sense of rootedness is personal for him. After earning his B.A. in political science and M.A. in psychology from Washington College, Matthews served as captain of the lacrosse team before taking his first campus job as lacrosse coach and assistant director of admissions. He went on to coach and teach at the U.S. Naval Academy for 12 years before returning to Washington Collge to hold multiple leadership roles—director of athletics, assistant to the president for special projects, associate vice president of administrative services, and interim vice president and dean of students. During that time, he completed his Ed.D. in Educational Leadership & Innovation from Wilmington University.

Off campus, Matthews’s commitment to Kent County has been just as steady. He has served as vice president of KRM Development Corporation, director of community and government relations for the Dixon Group, president of the Kent County Chamber of Commerce, and a board member for both the Mid-Shore Community Foundation and Kent County Character Counts.

Looking ahead, Matthews is energized by new initiatives such as the Warehime School of Business, made possible by a $15 million gift from alumna Beth Wareheim. The new building will stand at the campus entrance, symbolizing renewal. “It’s transformational,” he said. “Not just for business majors, but for students across disciplines.”

Still, he is pragmatic. “Washington College is a mission-oriented business, not a passion project,” he said. “We need to pay our bills, pay our people, and support our academic mission. Right now, the ship is stable—and that’s a good place to start.”

This video is approximately sixteen minutes in length.

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When John Lewis arrived at The Gunston School sixteen years ago, he wasn’t yet the seasoned Head of School he is today; he was a young educator drawn to what he calls “the ecosystem of school,” a living, breathing network of teachers, students, and ideas that thrive when curiosity and purpose align.

Lewis grew up in Montgomery County and attended a large public high school before heading to Georgetown University, where baseball first brought him to campus. But academics quickly took hold. “I became more of an academic than an athlete,” he says. His work as a resident assistant awakened a deeper interest in education, which led to his first teaching post at Culver Academies in Indiana.

From there, Lewis’s path wound through international schools in Quito, Ecuador, and Singapore, experiences that deepened his understanding of cultural and educational diversity. He went on to earn master’s degrees from both Harvard and Columbia before returning to the U.S. to take on leadership roles in New Jersey schools. When a headhunter called about “a little school in Maryland looking for a young leader,” he followed his instincts east and never looked back.

Sixteen years later, Gunston’s wooded waterfront campus just outside Centreville reflects Lewis’s philosophy of education as both intellectual rigor and ethical grounding. “We’re a community of choice,” he explains. “Families come because they believe in our values—academic excellence, personal attention, and environmental stewardship.”

While he trained as an English teacher, Lewis now teaches AP Government, a course he calls perfectly suited to today’s ever-changing political landscape. “There’s never a day without a major headline to discuss,” he says. The class keeps him close to students and grounded in the daily pulse of learning.

Lewis emphasizes that Gunston’s strength lies in its intimacy: a culture where no student can truly get lost, where teachers and students share respect for each other. “High school kids are a lot of fun,” he says. “Watching ninth graders arrive uncertain and leave as confident young adults; that’s the best part of this job.”

As both educator and parent—his own daughter is now a Gunston student—Lewis experiences the school from both sides. “It’s wonderful to see her challenged and supported by the same teachers I work with,” he says.

Throughout his role as Head of School, Lewis holds close to his guiding mantra: “The question ‘Where do I want to go?’ really begins with ‘Who am I?’ When students understand themselves, they make better choices—for college and for life.”

For those who have never visited the 75-acre campus along the Corsica River, Lewis encourages them to stop by.

This video is approximately nine minutes in length. For more about The Gunston School, please go here.

Publisher’s note:  The Talbot Spy has long hoped that it could work with the community’s young people to not only help them engage in journalism and storytelling, but reach an audience well beyond their school’s population. So it is particularly gratifying to begin a new periodic column dedicated to Talbot County students to share news stories and area profiles to accomplish those objective. Our first episode starts with The Country School’s India Smith and her questions for the school’s new head of school, Jay Parker. 

Talbot County students are encouraged to contact the Spy if they would like to participate by emailing us at [email protected].

Jay Parker is the newest head of Easton’s The Country School. I had the pleasure of sitting down for an interview with Mr. Parker. I learned a lot about Mr. Parker, from why he became a teacher to his plans for TCS.

My first question for Mr. Parker was, “Why did you decide to be a teacher?” Mr. Parker attended St. Albans School, a school similar to the Country School, as a child. He has fond memories of St. Albans, especially his high school history teacher, Mr. Suitor. Mr. Parker recalls, “He had a great sense of humor and connected with the kids. When I did decide to be a teacher, which was in my early twenties, I thought back to Mr. Suitor, and, you know, connecting with and caring about kids goes a long way.”

Next, we talked about the schools he worked at before coming to The Country School. Mr. Parker’s first job in education was in outdoor education. He worked for the Cape Cod school district and lived in Massachusetts. “It was fun to do outdoor ed because I got to teach the same thing every week to different groups of kids, so I could get better as a teacher.”

He left outdoor education and worked at Boys Latin in Baltimore for five years, then moved to Calvert School for ten years. He has been working in Colorado for the past four years as a middle school principal at Dawson School.

I was curious to know whether he had worked at any other jobs besides being a teacher. He thought for a moment and said he had pretty much been in education his entire career, but he did run a summer camp for twelve years. “I’d be able to spend most of my summers in Colorado or New Hampshire leading hiking trips, and that taught me a lot about everything from making websites for my business to doing the marketing and the accounting side of it, which I enjoyed, but I enjoy working with kids more than those types of things.”

Although he has close relationships with both Ms. Brune and Mr. Mufson, Mr. Parker has stated “Rule number one of being a head of school; don’t follow a previous head because everyone compares you to that head of school.” However, he said that “I’m very fortunate to have them as friends, because they’re amazing people.”

When asked how the job was going, he answered; “I feel blessed every day… Overall, what has blown me away is how inviting the school is. The teachers are all very caring and the people here work very hard all the time to support the kids. When people walk into our school, they can feel the love right when they come in.”

When I asked him what the main thing he’d like to accomplish in the job is, he said that TCS has a history of long term heads and that he had only ever worked at schools where the headmaster had been there at least ten years. “I feel like we’ve accomplished a lot this year, but you can’t really leave your mark on a school unless you’ve been there at least ten years.” Mr. Parker explained that he did not envision TCS ever adding a high school, but might add a program for kids aged 2–3.

“I think we’re going to own that idea of… tradition meets tomorrow… so, just filling in the gaps with better programming everywhere and ensuring the legacy of the school lives on.”

Then I asked a few less school-related questions. I was curious to know what his wife’s job was as well as what his family thought of Easton.

Mr. Parker explained that his wife was a counselor and had worked for Ms. Brune as a school counselor for nine years.

He said that he was originally from Maryland, so it was easy to adjust. “It’s also so cool that some people’s jobs are to be watermen or fix boats, and everyone in Talbot County is so connected to each other.”

Mr. Parker says he and his family are very happy in Maryland, and plans to spend the next decade at TCS, a time he believes is necessary to leave a lasting impact on the school and its students.

India Smith attends The Country School as lives in Easton. 

This video is approximately 12 minutes in length. For more information about The Country School please go here.

Saturday’s Baltimore Sun featured a front-page article about the ongoing financial and enrollment issues facing the college. The article, written by staff writer Jean Marbella, may be found here:

The Sun has a paywall but you can subscribe for $1 for three months.

Jennifer Kott is a College Success Manager at Talbot Mentors and a consultant for 7Sage, an admissions consulting group specializing in college preparation and law school admissions. Jennifer’s focus is on advising applicants how to maximize their chances for admission to the college or university of their choice.

“These days, the college admissions process has completely changed from the way it was when we were applying,” stated Kott. “Technology platforms have become both good and bad. But, once you figure out who you are and what you want, when you find the right fit, you’ll know it. There’s a college out there for every student. It’s just a long, arduous process.”

In Kott’s experience, students from first-generation, low-income, and demographically diverse backgrounds, with the right planning, guidance, and support, can sometimes qualify for admission to a more competitive college than they think. In recent years, students enrolled in Talbot Scholars program have attended Dartmouth College, Washington College, Towson University, American University, and the University of Maryland-College Park.

Jennifer Kott,

One area where parents and advisors can help is in prioritizing what’s most important to the student. “The best advice I can give to families is, first and foremost, get your student to take ownership of the process,” said Kott. “The primary role of parents and college advisors is to be a sounding board, to provide support and encouragement. Students and parents are consumers. Are the colleges you’re interested in responsive to you?”

Factors such as location, culture and community, academic focus, class size, career opportunities and cost – including financial aid – are all important. Kott suggests that the process needs to begin as soon as the student enters high school. “GPA trends over all four years are important. SAT, ACT and AP scores, if required, are not as important as before, but an improving trend in scores, as well as grades, always helps,” she said.

Kott also recommends that “Every student needs to come up with a checklist of ‘What does my favorite college look like?’ “The National  Association of College Admissions Counselors (NACAC) website is a very good starting place. Additionally, numerous college fairs are attended by many colleges and universities. Here’s where parents need to let the student take the lead and get to know the colleges they’re interested in attending,” she explained.

Critical to a successful college admissions process is the student’s individual essay. “A clean, clear, persuasive, big-hearted story reflecting the best version of oneself is vital to setting yourself apart from others in a crowded applicant pool. This is where having a good mentor, advisor or consultant is so helpful,” stated Kott.

She also thinks that is where lower-income, first-generation applicants can gain an advantage. “This is what we do at Talbot Scholars as well as 7Sage. Developing a student’s ‘soft skills’, such as writing, researching, and volunteering – both at school and in the community – is essential.”

While these elements are important, what really matters to many colleges and universities is that the applicant demonstrates engagement in their community and school. “Showcasing initiative, leadership, adaptability, and accountability are all important factors,” said Kott. “For example, having a part-time job demonstrates your work ethic.”

Kott believes there’s a college out there for every person who chooses to apply. Every student should have at least one reach (a college that is hard to get into) and one safe (a college that is easy to get into) college on their preferred list. “Education is a process, not an end in itself,” she noted. “There are numerous quality colleges that offer unique majors, internships, work-study programs, as well as learning centres that offer writing, math or other specialized assistance.”

Finally, college applicants should not rely merely on brochures and other promotional material provided by college admissions offices to attract applicants; campus visits are essential. “Parents should make sure their student takes the lead in contacting the Admissions Office and arranging a tour. Once you’ve done that, you’ll know if it’s the right fit!”

For more specific information, you can visit the the Talbot Mentors website here