When Maya Rao traveled to Italy with some friends for a Spring Break trip during her sophomore year, she wanted to know more about the history behind the places they visited.
Sean McShane, then a senior, satisfied everyone’s curiosities.
“He knew everything,” Rao, BC ’21, said. “Everywhere we went, we could point at like a statue and be like, ‘What’s that guy? What’s his story?’ And he was like, ‘That’s so and so.’”
Just over three years later, using this knowledge and a host of other information, McShane, BC ’19, won three rounds of Jeopardy!, collecting over $82,000 in winnings.
McShane, from West Islip, N.Y., said those around him knew him as a trivia buff growing up.
“Like even as a kid, I used to have all these dumb little facts,” he said. “People were constantly asking, ‘How do you know that? Why do you know that?’”
While in high school, he said he participated in his school’s quiz bowl team. He would often watch Jeopardy! Being a participant on the show was always an aspiration of his, and people would often tell him that he needed to be on it, he said.
At Boston College, McShane studied history and was a member of Hello…Shovelhead!, a sketch comedy group, and The New England Classic, a satirical magazine. McShane took the preliminary tests for the show while he was at BC as he hoped to appear on the quiz show’s collegiate tournament. But his Jeopardy! journey truly began in January of 2022.
The process for every Jeopardy!-hopeful begins with an online test of 50 random questions that are similar to those on the actual show, McShane said. Those who pass the first test are then placed in a lottery, and, if chosen from that lottery, are invited to take a Zoom-proctored test. From there, those who pass are put into another lottery. After being chosen from that second lottery, hopefuls engage in an interview, mock game, and submit an application, McShane said.
McShane said that a conversation with his friends one night sparked the idea for him to take the initial test.
“I really didn’t do any studying for the test,” he said. “It was kind of a spur-of-the-moment decision.”
Because he had seen the show so many times and done well as he answered along from home, he said he knew could make it on the show and win with a little strategizing.
“I was like, ‘Alright, if I can get on and I can figure out the buzzer, I think I have a good shot at this,’” he said.
After successfully completing each stage of the process, McShane said he found out that he was actually going to compete on Jeopardy! while at work in September 2022. He noticed he had missed a call from one of the producers, and when he returned her call, she said that she called to make sure the information on his application was all up to date.
“My heart was racing when I called her back because I’m like, ‘Is this it?’” he said.
Five days later, he said he received a text from the same producer, asking him to fly out to Culver City, Calif. at the end of October 2022 to tape the show.
“I was the first person to find out he was going to be on Jeopardy!” Rao said. “We were having dinner together, and he kept looking at his phone, and I was like, ‘What? What’s on your phone?’”
While she was not surprised that he was going to compete on the show, Rao said she was still ecstatic for him.
“It was one of those things where it made sense, but it was still so exciting to hear that he was gonna be on Jeopardy!” she said. “It was exciting.”
Robert McCrory, a friend of McShane’s and BC ’19, said he was also thrilled for McShane, as he knew that participating on the show was one of his dreams.
“I remember him mentioning in years past, like taking the tests and kind of […] what the Jeopardy! application process is like, so finding out that he was actually going to be on it, it was, like, it was just a lot of excitement for him, like I was excited on his behalf,” McCrory said.
Before taping, McShane said he received a package in the mail informing him of what to expect and outlining the rules of the game.
From there, his studying began to pick up.
“It wasn’t until I found out I was going on the show that I decided to actually study in earnest,” he said. “But it’s kind of like a fool’s errand because you have no idea what’s gonna show up.”
McShane said he had watched enough Jeopardy! episodes to know the common categories they test contestants on, such as U.S. presidents, geography, and Shakespeare. Once he knew he was going to appear on the show, he began spending numerous days memorizing world capitals, U.S. presidents and their vice presidents, English kings and queens, and other information from other probable categories. He also watched the show every night and sifted through past Jeopardy! games, quizzing himself on actual questions that had appeared on the show.
During this preparation, other than telling his immediate family, roommates, coworkers, and some others, he said he refrained from telling too many people that he was going to be on the show out of fear that he would perform poorly.
“I got the call [that] I was going to tape, and I didn’t wanna tell a lot of people because I’m like, ‘If I go out there and I just eat it, like I’m just gonna try to sweep this under the rug,’” he said.
Matt Wilson, BC ’21, said he called McShane one day to tell him a dumb joke. When McShane picked up, he could tell he was at an airport.
“I was like, ‘Why are you at an airport right now?’” he said. “And he … was trying not to tell anyone. He tried to pretend that he wasn’t at the airport, but it was very clear that he was, and then finally he’s like, ‘I’m going to California.’ But I said, ‘Why?’ and then he had to tell me he was going on Jeopardy!”
When he arrived, Jeopardy! employees touched up his hair and face with some makeup. Then, he went through a practice round on the actual stage, allowing him and several other competitors to get used to pressing the buzzer—the show invites about 15 competitors each day because it usually films five episodes per day.
McShane was chosen for the first round of filming that day. Though he got his first question wrong, he said he was in the lead by the first commercial break.
“By the first commercial of the first game, I was […] comfortable,” he said. “I had a good rhythm with the buzzer.”
By the end of Double Jeopardy!—the second round—he said he had a runaway game.
“I couldn’t get caught,” he said. “So, then I was freaking out in my head, like holy shit I just won Jeopardy!”
McShane said he does not remember too many details from his time taping—his nerves and his focus kept him locked in the game.
“Once they actually start taping, […] you kind of black out from the nerves,” he said.
Despite incorrectly answering his first Final Jeopardy! question, McShane won his first episode. From there, he said he was satisfied.
“[I told myself,] ‘Alright, I won an episode,’” he said. “‘I can go home. I can have a watch party. I can show my face. I can say I won Jeopardy!’ And after that [it was] just like, ‘Now I’m just playing for fun.’”
He went on to win two more games, winning three episodes of Jeopardy! in total.
Because there is a six-week delay between filming and airing, McShane could not tell anyone the results—he had to sign a nondisclosure agreement. But, because he had done well, he started telling people that he was going to appear on Jeopardy!
“Of course, the first question is: ‘How did you do?’” he said. “I was good about it. I said, ‘I can’t tell you.’”
Six weeks later, he said he invited a bunch of his friends to watch his first episode together at L Street Tavern in Boston.
“We all just kind of showed up that first night,” McRory said. “It was a Monday … and we just kind of all watched along with him, and …it was as if the Super Bowl was going on, and the Patriots were playing.”
Wilson was also there, and he said there were hundreds of people cheering him on at the bar.
“I trained up to Boston to watch it live with everyone else at L Street Tavern,” Wilson said. “He didn’t tell anybody [the results] … There were some times where we thought he slipped, and we got little hints, but either way [he was] good about not telling anyone, so it was hundreds of us in that bar cheering on.”
Between lifeguarding, working at a butcher shop, being on a tech company’s team, and winning Jeopardy!, McShane said he’s embraced an unconventional career trajectory.
“I am living off of my Jeopardy! winnings,” he said.
After winning the three episodes, Wilson advised McShane to take his victory as a sign to leave the job he had at the time, which he did not enjoy.
“I think he’s … really smart and talented and funny,” Wilson said. “And … I knew he didn’t like his job, and so I said, ‘Dude, this is your time. Go do something else.’”
Rao, who said she loved McShane’s Hello…Shovelhead! sketches, agrees that the intersection of his knowledge and his humor is one of his most special qualities.
“His jokes about life are really, really smart and really, really clever,” she said. “He’s not just somebody who’s very smart and knows a lot of things. He’s also very clever. And I think it’s really funny to watch somebody who can translate that knowledge into humor.”
