Leonard started his second day of Teen Jeopardy far behind his competitors. But after betting all of his $18,000 on a Double Jeopardy question, and answering correctly, he quickly jumped to the head of the pack.

For Final Jeopardy, Military Men was the subject. Leonard didn’t know the answer, but was confident he would end Final Jeopardy still ahead of his competitors, so he submitted a very daring answer instead. 

The first place prize for winning the game was a cool $75,000.

So sure he would win in the end, Leonard bet $0, and answered the Final Jeopardy query of “On June 6th, 1944, he said, ‘The eyes of the world are upon you,'” with, “Who is some guy in Normandy, but I just won $75,000.”

And he did.