Tom Flynn '83

Champions of Giving: Thomas Flynn '83

Meet the Donor

Thomas Flynn ’83 is a proud alumnus, longtime supporter, and current Vice Chair of Austin Prep's Board of Trustees whose relationship with the School spans more than four decades. First arriving on campus as a freshman in 1979, Tom attended Austin Prep when the campus was still growing, and the faculty’s commitment to students was already shaping the School’s culture.

“What was really impactful about Austin Prep then and now was the strength of its faculty,” Tom shared.

 

From the beginning, Austin Prep shaped both Tom’s academic foundation and the person he would become. Through rigorous coursework, deep relationships with teachers, and a culture rooted in Augustinian values, Tom developed the habits of thought, accountability, and curiosity that carried him through college, graduate school, and a successful career.

“My teachers’ influence on me here was incredibly impactful,” he said. “If you think back on your life and you segmented it into four to five-year segments and say, which of those was most impactful in my formation as a person and the person I would become? For me, Austin Prep is one of the top.”

The Inspiration to Give

 

As Tom reflected on the teachers who shaped his life, three names consistently stood out: Roger Stone, Bob Hennessy, and Gary Mackiewicz. Each dedicated about five decades of their lives to Austin Prep, forming generations of students through academic excellence, mentorship, and lived values.

When Tom returned to campus years later as a trustee, the continuity of these educators left a lasting impression.

“One of the first things that struck me is that Roger and Bob and Gary were all still teaching here,” he said. “It said something about their dedication to their craft, their loyalty to the institution, and the school’s ability to retain such talented teachers.”

Tom saw firsthand how these faculty pillars shaped not only students, but the culture of Austin Prep itself.

“When you can have that kind of faculty stability in an institution like this, there’s so many benefits beyond the thousands of students that Roger, Gary, and Bob taught over the years,” he shared. “The values that this school has always lived by, lives on in its people.”

Honoring the Teachers Who Shaped a Generation

When Tom was offered the opportunity to name spaces on campus, he chose to honor the educators whose influence extended across decades.

“I was here for four years, and I know three people who were here for 40-plus years and their impact on this school and on the thousands of students who’ve gone through their classes is just so dramatic,” Tom said. “So for me, it was such a no-brainer to name classrooms in their honor. They deserve it and they really are pillars of this school.”

Roger Stone

 

Roger Stone devoted more than a half century to Austin Prep as a Latin teacher, historian, theater director, mentor, and instructional coach. His approach to education emphasized community, service, and critical thinking rooted in Augustinian values.

“Your students have to be your cause,” Roger shared. “It is personal and it isn’t ticking off the boxes of a curriculum.”

Reflecting on Tom’s gift, Roger recognized it as a natural extension of Austin Prep’s culture of alumni engagement and giving.

“When I first heard that Tom Flynn was making a generous donation to the school and wanted to do it honoring Bob, Gary, and myself, I was very flattered,” he said. “My really first reaction was how much this is in the pattern of Austin Prep students. He has become that Austin Prep student who becomes a parent, who becomes a trustee, who gives back to the school.”

Bob Hennessy 

Classroom Named in His Honor 

 

Bob Hennessy spent 47 years teaching at Austin Prep, primarily in world languages, while mentoring generations of students through classroom learning and immersive travel experiences across the world. After he "retired" from full-time teaching, Bob stays on at Austin Prep as a substitute teacher. 

“For me, it’s really been my whole life,” Bob said of Austin Prep. “I’ve been here since I graduated from grad school and I’m still here now.”

Bob saw Tom as a living example of Austin Prep’s long-term impact.

“It’s been over 40 years since he was here as a student, and he’s come back as a trustee,” Bob shared. “He’s a very generous donor to the school, and he’s often here for school events, so you can see the impact there in his life.”

Upon learning a classroom would bear his name, Bob reflected on the legacy it represented.

“It was something of me that can stay here in the school after I’m gone,” he said. “So I was very, very happy.”

Gary Mackiewicz 

Classroom Named in His Honor 

 

Gary Mackiewicz served nearly 50 years as a French teacher, and mentor whose passion centered on forming meaningful relationships with students.

“The values of the school matched my own personal values,” Gary said. “It empowered me because I felt like I could make a difference, not only in the lives of my students, but in the broader school as a whole.”

Learning of Tom’s gift left him deeply moved.

“When I first heard that Tom was donating money, a classroom in my name, honestly, I was surprised, if not shocked,” Gary shared. “Clearly, I felt very honored by this.”

For Gary, the recognition reaffirmed the heart of teaching.

“When you get a sense of that gratitude coming back to you, ‘Well, that’s wonderful. That’s why we’re in this profession,’” he said.

Why Giving Matters

 

For Tom Flynn, supporting Austin Prep reflects gratitude and responsibility. “I feel tremendously grateful to Austin Prep for the education I received here,” he said. “I feel grateful to be able to give back, to serve on the board, and to help ensure the School can do for future generations what it did for me.”

He believes Austin Prep’s continued growth depends on the generosity of those who love it.

“It’s so important for those of us who love Austin Prep to support Austin Prep,” Tom shared. “Nothing at a place like Austin Prep happens by chance. It’s all intentional.”

By naming classrooms in honor of the teachers who shaped his life, Tom has created a lasting tribute to the power of dedicated educators and the enduring impact of an Austin Prep education.

Their names now stand as daily reminders to students of what great teaching, mentorship, and community can accomplish.

       

Become a Champion of Giving

The article above is part of our Champions of Giving series, which highlights the individuals and families whose generosity transforms student lives and strengthens the Austin Prep experience. You too can be a Champion of Giving by supporting our students through annual giving, memorial scholarships, or campaign contributions. Your gift helps students learn boldly, lead with purpose, and serve with compassion — creating a lasting impact for generations to come.