What Is … a Dream Come True?

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What Is … a Dream Come True?

Michael Kavanagh, principal of Holy Family Catholic School, competes on an episode of Jeopardy! that aired Nov. 24, 2025. | Courtesy of Michael Kavanagh

For as long as Michael Kavanagh can remember, he dreamed of what it would be like to be a contestant on Jeopardy!

That dream became a reality recently when Kavanagh, principal of Holy Family Catholic School in Jacksonville, earned a spot on the iconic television game show during an episode that aired Nov. 24.

“My uncle was actually on Jeopardy! in 1988, and although I was only three or four years old, I remember it being such a big deal,” Kavanagh said. “As a kid, we watched the show every day. How many people can say, ‘I had this dream when I was eight years old, and then I did it?’ It lived up to everything I imagined.”

Roughly 70,000 people take the online test each year in hopes of making it onto the show. Only about 450 are chosen.

“Just getting into the studio and having the opportunity to compete is the true monumental challenge,” he said.

Taking the test had once been an annual tradition for Kavanagh throughout his 20s, but nearly a decade passed before he considered it again. That changed last spring when his brother texted him after hearing the show might bring back a teacher tournament.

“It turned out they weren’t doing that, but I was already on the website and figured I had 10 minutes, so I took the test anyway,” Kavanagh said. “I felt like I did pretty well, but I had no expectations.”

A few months later, an email from the show’s producers arrived. After additional rounds of testing, his expectations grew with each step.

“Since the episode aired (Nov. 24), hearing from the students and parents who watched and seeing how supportive the Holy Family community has been means the most to me,” he said.

As a principal, Kavanagh strives to inspire his students and hopes his appearance on Jeopardy! demonstrates what can happen when someone continues to work toward a passion.

Kavanagh finished second in the game but was the only contestant to correctly answer the Final Jeopardy! question, which focused on sports history.

“I saw that category come up and thought, ‘I think I’ve got this one,’” he said.

As a Catholic, Kavanagh often reflects on God’s purpose in his life. After the show, contestants mingled with audience members. While searching for his wife, he met a couple who introduced themselves as educators.

“They turned out to be the parents of Harrison Whitaker, the contestant who won that day,” Kavanagh said. “His father, Todd, is a former principal and the author of What Great Principals Do Differently, which I had just finished reading.”

Kavanagh told Whitaker how much the book had influenced his career.

“How often do you get to tell someone you just met that they had such a profound impact on your life?” he said.

The two have stayed in touch, and Kavanagh hopes to invite Whitaker to speak with teachers at Holy Family, or even across the diocese.

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