A little intimidated, a boy with shaggy brown hair shuffled into Mrs. Jaramillo’s English class on the first day of freshman year. Although he would switch to another English class the next day, he still had to go through the obligatory “Introduce Yourself to the Class.” He cleared his throat and confidently said, “Hi, my name is Alan Koolik. I’m from Boca Raton and I want to be on Jeopardy.”

Since his informal introduction, Alan Koolik was known by many of his classmates as the know-it-all trivia guy. Often seen in his spare time on the Jeopardy archive website, Alan constantly tested his knowledge of trivia, stretching his mind from Broadway history to pop culture. He was the guy students (and teachers) went to if they had any random questions on their minds. He was the guy who corrected teachers if they incorrectly recalled a history fact. Throughout his three years at the Pine, Alan won numerous geography and trivia bees, yet his dream remained the same: compete in the “Teen Jeopardy!” Tournament one day.

Three years later at Sony Picture Studios in California, he had made his dream a reality. As one of 15 select teenagers from around the country, Alan was competing in the annual tournament hosted by trivia icon Alex Trebek. Up for grabs was much more than pride and a once-in-a-lifetime experience to fight for a $75,000 prize.

Interviewed after the tournament’s airing this past July, Koolik said that the experience itself was more than he could have ever imagined. “It was definitely a dream come true; it took more than three years to qualify so I was just excited to be there,” said Koolik. “I had an amazing time.”

Alan’s journey of qualifying for the tournament was much more strenuous than the five hour flight to California however. After 3 years of attempting the online Jeopardy test in September, he finally qualified to the second round of selection two months later in New York. This stage included yet another written test, an interview, and several mock games against other potential candidates to master his buzzer skills and on-camera appearance.

Alan impressed the Jeopardy scouts and was notified in February of his acceptance into the tournament, to be pre-filmed in early March.

“My dad got a phone call…I don’t generally go crazy about things, but certainly I was very excited about my selection,” said Koolik.

Amidst this time off, Alan’s already-impressive trivia training went into overdrive as friends and family quizzed him wherever he went. “[Jeopardy] was already my obsession before, it just became even more of a commitment,” said Koolik.

And the preparation paid off too. Despite facing stiff competition throughout, Alan breezed through to the two day final of the tournament and established himself as a fan favorite. With his calm, collected approach to a stressful game, he dominated the competition with class heading into the championship.

The format of the two day final consisted of two separate games of Jeopardy, where the contestants’ winnings of both days would be tallied up to crown the champion. After establishing a healthy $10,000 lead after day one, Alan seemed destined to reign over his opponents Jeff Xie of New Jersey and Cooper Lair of Arkansas.

Then the unthinkable happened. Following the final jeopardy of day two, Jeff realized that he had equaled Alan’s $10k lead from the previous game, resulting in a tie! Both boys had finished with $54,200.

In what was one of the closest matches in Jeopardy’s 30 year history, Alan and Jeff were to duke it out in a single tiebreaker question read immediately by Alex Trebek. Whoever buzzed in and answered the question correctly would win.

The Question: “The Battles of Shiloh and Collierville were fought in this state.”

Jeff Xie was the expert buzzer throughout the tournament and his adept reaction skills paid off again. Despite knowing the answer, Alan buzzed in a split second after his competitor, who answered “What is Tennessee?” and won the tournament.

And just like that, Alan lost. It was certainly as anti-climactic as it gets for Jeopardy fans. For the tournament’s first ever tie, was a single question to decide the champion an adequate solution? Nevertheless, for Koolik the manner of the defeat was hard to swallow.

“It’s been hard to digest, even now, four months later. I was aware of what the tiebreaker format was before the show, but I just wish it was different. I would have liked Alex to have a list of questions, similar to Final Jeopardy, which Jeff and I were to write down the answers to. We would keep going until someone messed up.”

Yet nobody, including Alan’s closest friends and family knew how he fared in the tournament until it aired several weeks ago. Alan kept his lips sealed until the airing of the tournament concluded on Friday August 1^st, to the dismay of his closest friends and family.

So on that Friday night, surrounded by close friends and family during the air of the show’s finale, he relived his incredible defeat.

Don’t feel too bad for Alan though.

He still walked away with a meager $54,200 and an “unforgettable experience.” The senior is an aspiring engineer applying to some of the nation’s most prestigious schools. And don’t count out Alan’s future Jeopardy aspirations yet. While he is no longer allowed to compete in Alex Trebek’s Jeopardy, should there be a new game show host in the show’s future, Alan would be allowed to compete again. Trebek’s current contract is due to expire in 2016, so this is a certain possibility. Until then, good luck Alan, and go work on your buzzer skills!