Titus Redmond (L), a longtime educator at Leo Catholic High School, received Big Shoulders Fund’s $10,000 Impact Educator of the Year Award (Photo Provided).
A South Side Chicago teacher recently received a $10,000 award for his lasting impact on his students and school.
The Big Shoulders Fund awarded its Impact Educator of the Year Award to Leo Catholic High School’s Titus Redmond, a longtime educator who embodies the qualities of an educational leader, according to his principal.
“With 25 years of dedication to Catholic education, Mr. Redmond isn’t just a great teacher—he’s a mentor, leader and role model who has left a lasting impact on Leo Catholic High School and the young men we serve,” said Shaka Rawls, Leo High School’s principal. “Leo Catholic High School is better because of Mr. Redmond, and we are grateful for his unwavering commitment to our students and our mission. He is more than deserving of this recognition.”
Rawls and a select committee nominated Redmond, who received a one-time $10,000 award. Impact Educator of the Year honorees have to teach at their schools for no less than two full years before being nominated.
But for Redmond, the award is confirmation for his years of work in the classroom and beyond it at the all-male Catholic high school in Auburn-Gresham.
“Winning the Impact Educator of the Year Award is an affirmation of the work I’ve poured into this calling; not just writing lesson plans or preparing for daily instruction, but building real, lasting relationships,” Redmond wrote in a response to questions emailed by The Chicago Defender. “It’s the phone calls I make home, the weekends spent planning, the tough but necessary conversations I’ve had with families.”
Redmond shared more with The Defender via email about the importance of teaching young men identity and confidence, the moment he knew he had made a difference and what keeps him motivated after being in the classroom for a quarter century.
“Just Keep Showing Up”
How do you manage all your roles while still connecting with students?
“I manage by always remembering why I do this work. Whether I’m coaching a team, leading a curriculum meeting, or responding to a family concern, I center myself in the understanding that at the heart of it all is a student who deserves my best.
I’ve built routines to stay organized, but I also permit myself to be human, and that authenticity is what helps me stay connected to my students. I’ve learned they don’t need me to be perfect; they need me to be present.
So, I prioritize showing up, as someone who listens, holds them accountable, and believes in their potential every single day. I want them to feel that they’re cared for. That’s rooted in my role as a parent. I try to treat every student the way I’d want a teacher to treat my own children: with consistency, compassion, and a belief that they matter.”
Teaching Confidence and Identity
What’s the most important lesson you try to teach your students?
“I teach them to be themselves and to know that who they are is enough. They’re powerful, worthy, and capable just as they are. I want every student to understand that their story matters, that their voice carries weight, and that they don’t have to wait until adulthood to make an impact.
Whether we’re reading James Baldwin or writing college essays, I’m always reinforcing that knowledge is power, but identity is strength. Once they embrace who they are, no one can take that away from them.
But I also remind them that growth requires effort. Every day is a new opportunity to be just 1% better than the day before. That daily commitment to themselves, to their learning, to their future, is what makes all the difference.”
When a Ride to School Meant Everything
Can you share a moment that illustrates how your work has made a difference?
“Last year, I led a schoolwide initiative focused on improving attendance. After completing a leadership program over the summer, I came back ready to tackle the challenge. I started by analyzing our data and quickly noticed a troubling pattern: a senior who was missing school two to three times a week.
After some tough, honest conversations with him, it became clear that his graduation was in jeopardy, not because of academics, but because of chronic absences. We brought in his family for support, and that’s when we uncovered the real issue: transportation. The student was too proud and too embarrassed to admit that he couldn’t always afford bus fare. He thought that by speaking up, he would be letting his mother down.
In that moment, it became clear that this wasn’t a discipline issue—it was a dignity issue. My team and I went to our school president, explained the situation, and secured funding to cover his transportation costs.
That small act, a conversation, some advocacy, and a bit of logistical support, changed everything. That student didn’t miss another day. He walked into school with his head held higher because the barrier had been removed. And months later, he walked across the graduation stage with pride.
That moment reminded me that sometimes advocacy doesn’t look like a grand speech or a major policy change. Sometimes, it’s just listening closely enough to find the real problem—and being willing to do something about it.”
What Fuels the Fire After 25 Years
What keeps you motivated after 25 years in education?
“At my core, I’m a lifelong learner. I’ve always wanted to be a reflective practitioner—someone who doesn’t just teach, but grows, questions and evolves. What keeps me coming back, year after year, is the students. Every class that walks through the door brings fresh energy, brilliance, and dreams—sometimes wrapped in doubt, but always full of possibility. That keeps me learning. It keeps me laughing. And most of all, it keeps me leaning in.
What also fuels me is the belief that schools should be places of liberation, not just compliance. I’m motivated by the opportunity to help shape that vision alongside fellow educators, to build a school culture where every student’s full humanity is honored and affirmed.
Even after 25 years, I still feel like I’m just getting started. After completing a leadership program, I made the decision to go back to school myself. I’m now entering a doctoral program because I want to be pushed academically, and I want to bring back best practices that will benefit my students and colleagues in meaningful, forward-thinking ways.
At the end of the day, my motivation is simple: the desire to get better. Just like I challenge my students to be 1% better every day, I try to live that challenge myself.”
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