Rockford native Lloyd Sy, right, an English professor at Yale University, poses for a photo with “Jeopardy!” host Ken Jennings in January 2024 after a tapping of Jeopardy! Champions Wildcard. (Photo provided by Lloyd Sy)
By Kevin Haas
Rock River Current
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ROCKFORD — Lloyd Sy took a new approach to preparing to compete on “Jeopardy!” for his second run on the show.

The 2012 Auburn High School valedictorian, who is now an assistant professor of English at Yale University, tested his intellect with the help of artificial intelligence. He asked ChatGPT, an AI tool that can generate text and conversation on demand, to play the role of “Jeopardy!” host and ask him questions on his weakest categories.

Those topics: automobiles, food and drink, and pop music from the 1970s and ’80s.

“These are all topics that come up regularly on Jeopardy!,” he said in a phone interview with the Rock River Current. “It was a way to quickly learn the topics I was worst at, and it was really well suited for the task.”

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Sy has also practiced by using a ballpoint pen as a buzzer and having friends fire questions his way.

Viewers will find out Wednesday how the preparation paid off for Sy, a 29-year-old Rockford native who had a three-day run on “Jeopardy!” a year ago. That run came with two victories, including dethroning a super champion who had 13 straight wins. He earned $53,578 by winning on two consecutive shows.

Now, he’s pitted up against Dillon Hupp and Kelly Barry, who also knocked off a multi-day winning champion, in Jeopardy’s Champions Wildcard.

The competition allows contestants who won one or two games to compete for the final two spots in the 2024 Tournament of Champions.

Sy filmed with “Jeopardy!” the first week of the year, but he’s sworn to secrecy on the results until after it airs.

Returning to the show brings a different feel, as competitors are all familiar with everything from the production to the lights and the feel of the buzzer in your hand. It also comes with the ability to have a scouting report on your opponents, who have all played in televised games.

“You’ve seen all the people play, and so you know what they’re good at and what they might not be good at, and that does fold into your gameplay a little bit,” Sy said.

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Outside of “Jeopardy!,” Sy is teaching his first classes at Yale, where handles courses on Native American literature.  Sy got his bachelor’s degree from Brown University, and his master’s and Ph.D in English from the University of Virginia, where he was also a Jefferson Fellow. 

He’s also currently working on transforming his dissertation into a book, which examines the 19th century writings of indigenous people facing deforestation from colonial settlers who removed trees as they built new cities.

“There’s a huge difference between what I do in my professional life and what I do on Jeopardy,” Sy said. “My research involves doing one very specific thing in a very specific time period and just doing everything about that.”

“Jeopardy!,” meanwhile, depends on having rapid reflexes to answer questions on a wide variety of topics. In that way it can be a game of chance depending on whether the categories fall in your areas of expertise, he said.

There are at least some similarities between success in academia and on “Jeopardy!,” Sy said. Both depend on having a natural curiosity about the world and a desire to always look for ways to learn.

How to watch

“Jeopardy!” airs at 4 p.m. and 4:30 p.m. on NBC (13 WREX). You can also go here to find your local channel. Lloyd Sy’s episode airs on Wednesday.


This article is by Kevin Haas. Email him at khaas@rockrivercurrent.com or follow him on X at @KevinMHaas or Instagram @thekevinhaas and Threads @thekevinhaas

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