There are places you remember with your mind, and places you remember with your whole body. For Leroy Anthony Weeks, Randolph-Macon Academy is one of those places: a hilltop that didn’t just change his surroundings, but reshaped his sense of what was possible.
Coming from the Bronx in the early 1980s, a world marked by fires, drugs, gang violence, and deep inequities, Leroy didn’t realize how much he had been carrying until he finally stepped away from it. But as his family drove up the hill to R-MA in January of 1984, he felt something shift. In his words, it was like “leveling up to a different place”, a place where mentorship, structure, and belonging helped him rise into leadership and become the person he is still grateful for today.
Leaving the Bronx Behind
Leroy grew up in the Bronx in the early 1980s, a time he describes as defined by hardship and instability.
“I’m from the Bronx,” he said. “In the early 80s, the South Bronx in particular was ravaged by lots of fires. An epidemic of drugs, and an epidemic of gang violence. Inequities, that was my world.”
And like many young people, he didn’t have the context to realize how abnormal it was.
“I didn’t know something wasn’t normal until I got a chance to get away from it.”
That chance came when his parents made a decision that would reshape the rest of his life.
“I owe everything that I am now to the parents that made the decision that they made then, which was to send me off to school and find a different path.”
A Different Kind of Environment
For Leroy, stepping into R-MA wasn’t simply changing schools. It was entering a new world, one with structure, safety, and possibility.
And for those around him, Leroy stood out right away.
Mike Starling, a former Commandant of Cadets, first met Leroy during their time as students at R-MA. Even then, he saw something different.
“I met Leroy. We were both sophomores together, and he struck me as different even as a sophomore,” Mike said. “He was driven; he was very purposeful. I very much admired that in him.”
Mike explained that he came to R-MA for structure and focus. But meeting Leroy shaped something deeper.
“I ran into Leroy Weeks here, and I got much more serious about what I was going to do as an adult.”
Becoming a Leader Because Someone Believed He Could
Leroy’s story is not just about escaping hardship. It’s about what happens when a student is truly supported by peers, mentors, and a community that refuses to let them shrink.
“Without question, the things that I have achieved now came about because I had the people that I’ve come to know and love take an interest in me and influence me from this school,” Leroy said.
One moment in particular changed everything.
“Ninth grade, Jerry’s a dear friend of mine. He said, ‘Well, you should try for the drum major spot.’ I said, ‘Really? You think so?”
That small encouragement turned into steady practice, mentorship, and belief.
“During my Friday evenings, I’d be out here with another one of my schoolmates. We’d just practice moves. He’d give me feedback. At the beginning of sophomore year, I tried out and got the job.”
Leroy became R-MA’s first African-American Drum Major, and later, its first African-American Corps Commander.
And for him, the significance was personal.
“This inclusive nature was just such that it made me feel like I could do anything.”
The R-MA Journey: Boy to Man
Leroy describes his time at Randolph-Macon Academy in a way that captures what many families hope for when they choose our private boarding school: transformation.
“When I left New York, I was a kid, I was a boy,” he said. “The R-MA journey was the thing that separated the boy from the man.”
Mike watched Leroy’s growth up close, and it changed him, too.
“He helped me get serious about myself,” Mike said. “It’s a powerful experience to have a peer who’s laser-focused, absolutely driven about a purpose for his life.”
Mike followed Leroy’s example and found his own leadership path.
“I watched Leroy. I used him as an example and tried to do what he did. As a senior, I was a cadet officer, and that gave me the confidence to go on to college and into the military.”
The Leadership Lessons That Last
Today, Leroy is the Director of the National Case Assistance Center for the Social Security Administration. But he traces his foundation back to R-MA, not just in career success, but in who he became.
“I remember coming out of that chapel after graduation day, thinking, ‘Oh my gosh, I’m so glad that I had my formative years on this hill.’”
And the impact didn’t stop at graduation.
“My time here allowed me to be the best father, best employee, and best director that I could be,” Leroy said. “My kids get the best part of R-MA because I infuse them with that whole idea of integrity, because I learned it here.”
He also carries R-MA into his professional leadership.
“As a boss, they get that because I came here and I learned something about character and leadership.”
A Community That Keeps Giving Back
Mike returned to our preparatory school in Virginia as an adult because the experience stayed with him and because he believes in passing it forward.
“I came back to Randolph-Macon Academy because this was a great experience for me,” he said. “It’s great to watch young kids develop into who they’re going to be, and to help influence them to actually do that.”
Leroy echoes the same feeling: gratitude, connection, and lifelong belonging.
“This place changed my life in ways I’m still unraveling,” he said. “I’m very thankful that I have the friends and really family members that I’ve acquired from my time here.”
And perhaps the most powerful summary of all is the one he leaves us with:
“We rise together by working together and learning together.”
Watch Leroy’s inspiring journey here.
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