Yale University English Department

Lloyd Sy, a new professor of English, has appeared three times on “Jeopardy!” His most recent appearance was on Jan. 24, when he reached the semifinals and won $10,000. 

Sy, who became a professor of English in January, comes to Yale having won a sum of $65,000 in three appearances on “Jeopardy!”

His most recent appearance was in the Champions Wildcard tournament. He had previously appeared on two episodes in January 2023, while pursuing a doctorate in English at the University of Virginia.

Getting onto the show involves a challenging process, Sy said. First, one has to pass a fifty question online test assessing general knowledge, a test he took while in Starbucks one day. One then advances to another test, this one proctored via Zoom to prevent cheating. Finally, one might be invited to an audition on Zoom that involves a mock game of “Jeopardy!” played with other candidates.

“At this point, they are really not testing your knowledge anymore,” Sy said. “They’re entirely testing how you look on camera.”

He prepared accordingly. “I put a whole bunch of lights on myself and smiled the whole time. I think I got half of the questions wrong, but I was smiling the whole time.”

This was in July 2022. Three months later, he was invited to appear on the show. He taped two episodes in November, which aired in January 2023, and won $55,000.

His graduate stipend at the time was $26,000. He had earned more than two years’ income in less than two hours. “It was good,” he said.

He came back this January for the Champions Wildcard, a tournament for people who’ve already participated, and “embarrassingly” lost on a question about literature, he said. 

Despite this, his literary studies have cultivated a skill — reading — that has been key to his success. “I’m always reading,” he said.  “I always pop in an audiobook when I’m walking anywhere.”

He guessed that he reads 130 to 150 books a year. He just finished a novel by Japanese Nobel laureate Yasunari Kawabata and is now reading, among other things, the poetry of William Cullen Bryant and a biography of Pope John Paul II.

His eclectic reading meant that he came to “Jeopardy!” with a diverse knowledge-base, even though he said he “didn’t really extensively prepare.”

But success took more than trivia knowledge. According to Lucas Miner ’24, who appeared on “Jeopardy!” in 2019 and 2023, “The real trick to ‘Jeopardy!’ is being good on the buzzer.”

Most contestants know the answers to most of the questions, he explained; the “trick” is being fast enough for it to matter.

Sy — who got lots of buzzer experience on his high school quiz bowl team — relishes this part of the game. 

“I love the excitement of being on a buzzer,” he said. 

For all intents and purposes, though, Sy’s “Jeopardy!” career is now over, he said.

It is rare for non-champions to be invited back once; twice is almost unheard of.

That suits him fine. “I’ve taken enough money from the ‘Jeopardy!’ cow,” he said, “and I’m eager to put it behind me.” 

This semester, he’s teaching “The Native American Renaissance,” a first-year seminar on the “flowering of Native literatures” after 1968, as the syllabus puts it. 

Kylie Morris ’27, who is in the class, said that Sy avoids talking about his “Jeopardy!” career. She said he treats it as if “it was nothing.”  

Nonetheless, she said he comes across as the kind of person who would appear on the quiz show. 

“He makes me think of a mad scientist sometimes,” she said. “He gets these ideas and he goes off on these tangents, and they’re all really interesting. And then all of a sudden he’ll pull out a bizarre fact.”

For example, she said, one day in class someone sitting next to her said the word “belong” — to which he responded, “Actually, I wrote a fifteen page paper on the word ‘belong’!”

Morris highlighted Sy’s empathy and effectiveness as a teacher. She said that he can understand when a student is struggling, and that he always wants to have “those one-on-one chats.” She added that he is also good at relating his lessons to personal life experience.

Looking to the future as a new professor, Sy said he is looking forward to using Yale’s resources for research, including the Beinecke Library. 

“Yale is one of the best places in the universe to do research,” he said. “This is a wonderful place to build things. I don’t think I’ve even gazed upon what I could do yet.”

Yale has been affiliated with many “Jeopardy!” contestants, including Matt Amodio GRD ’23, who won a record-breaking 38 games in a row.

Update, Feb. 19: This article has been updated to remove repetitive language.