From the start of the first installment of the two-day Jeopardy! College Championships final Thursday, the game never went UC Berkeley junior Kevin Shen’s way.

The trivia show started with a seemingly easy pick — six-syllable words for $200 — that went unanswered by Shen and his two competitors, Terry O’Shea from Princeton University and Tucker Pope from Texas A&M University. The six-syllable word category ultimately hurt more than benefitted Shen, who missed the $1000 question.

Round one ended with Shen trailing in last with $2,200 — $1,000 coming from answering the last question on the genus of the komodo dragon (Answer: Monitor). While Shen eked past Pope for second place by the end of round two, Shen fell back to last place with $8,765 after missing the Final Jeopardy question. O’Shea finished ahead in first place with $19,800.

O’Shea and Pope shared the three Double Jeopardy chances, limiting Shen’s opportunities to separate himself from the competition.

But in the Final Jeopardy round, for which the topic was “Authors,” Shen failed to end his day on a high note. The question was, “On his death in 1862, a Massachusetts paper said, ‘No man ever lived closer to nature, and reported her secrets more eloquently.’”

The answer was Henry David Thoreau, a transcendentalist author who wrote “Walden.” O’Shea and Pope wrote Thoreau. Shen wrote Ralph Waldo Emerson, a fellow transcendentalist author from Massachusetts.

The winner of Jeopardy! College Championships will be determined by the combined scores of both days after Friday’s contest.