Kennedy Robertson

Connect Tell us why you became a teacher

I became a teacher reluctantly, but the kids pulled me in. I saw how much they needed someone real—someone who saw them, believed in them, and gave them the tools to win in life. Teaching isn't just a job; it's being the bridge between 'Yale or jail,' Wall Street or 'the streets.' It's showing up when no one else does, being the right voice at the right time. My class isn’t just a place to learn—it’s the place to be. I teach because every kid deserves someone in their corner.

Tell us about your most memorable teaching experience

One of my best moments was watching a former 5th grader hit the game-winner to seal his high school team’s undefeated season. I was coaching (when I shouldn’t have been), but after the game, we talked, and I realized I had taught him more than basketball—I taught him leadership. Another was a 5-year-old mimicking my every move. It reminded me that kids watch everything. Some need discipline and fun, but my goal is always the same—**to show up, set the example, and leave a lasting impact.

What would you do with the $25,000?

I’d invest the $25K to create more opportunities. As a teacher in a rural area, I’d use it as a down payment on affordable teacher housing to help with retention in underserved communities. I’d also develop a specialized academy to identify young leaders early, train them in business and politics, and teach them to lead compassionately. I could combine both—housing for teachers who develop future leaders, ensuring we build a pipeline of impact for generations.