Stevie Ruiz of Montauk said he first hit his stride on “Jeopardy!” in early December, an experience that netted him $38,987 over three days, when the category Artists by Album popped up on the board.
“ ‘Black Album,’ ‘Reasonable Doubt.’ Who was Jay Z?” he said, giving an example from the category. The following evening, he again went on a run when a Fast Fashion category hit the board.
“Love fashion categories,” he said. “Not a lot of people on there are into fashion, but I love those.” On the other hand, of the common subjects, Mr. Ruiz said he struggles most with opera, ballet, and Broadway.
The journey began for him when he was young, around 4 years old. At about that age, he answered a question on the show for the first time. His mother and grandmother, who were watching, looked at him like, “What just happened?”
“I’ve always been one to be able to answer along with the TV,” Mr. Ruiz said. “I learned to read when I was 2. I’ve always had a lot of curiosity. I love learning new things, and I’ve always had a good memory.”
Eventually, around six years ago, Mr. Ruiz began taking the online test to appear on the show. Applicants can take it once a year, and “if you get 35 of the 50 right — or at least that’s word on the internet because they don’t really tell you — then you get to audition.” Outside of a confirmation email, he did not hear back, or so he thought.
Mr. Ruiz took the test again last year, and for the first time he noticed that the confirmation email instructed him to add two email addresses to his contacts so that future emails don’t go to a spam folder.
“Oh, I never thought of that before,” Mr. Ruiz recalled. “Wouldn’t it be crazy if they emailed me?” So, he checked his spam folder.
There he found that three years ago, the show had tried to reach him; upon finding that, he replied to the email asking if they could “please, please let me” audition. The “Jeopardy!” team responded, inviting him to an audition, which happened in March.
After completing the final audition — which occurred for him in June — contestants are placed in a pool for two years. Mr. Ruiz told himself he’d stop thinking about it until June 2026. Then, in August, the show invited him on.
To prepare, many contestants make flashcards and study the “Jeopardy!” archives, which have compiled every answer since Alex Trebek started on the show in the 1980s.
“I didn’t have time to do any of that,” Mr. Ruiz said. “During the season, I work six days a week. I have my Haitian food pop-up, just launched a clothing line — wearing it — so I have all kinds of things happening, and I have a social life, and I have family.”
Nonetheless, once there, his reflexes kicked in once the nervousness dissipated.
“It’s a blur,” Mr. Ruiz said of going onstage. “It’s almost like being in a fugue state.” Before going up, contestants can participate in a rehearsal to “play around with the buzzer” and get a feel for what it will be like when it’s live.
During introductions, Mr. Ruiz talked about Yotte’s, a Haitian food pop-up named after his grandmother that he runs in Montauk.
As for his nerves, “When the audience was in there and I was going up, it still felt like a dream, but it was time to focus,” he said. “I was nervous for like a second. You can see it in my first episode — when they were introducing me — my lip twitches a little bit, but then I just took a deep breath.”
At the end of his first night, Mr. Ruiz had a relatively narrow lead when Ken Jennings revealed the Final Jeopardy category, 19th-Century European Literature, and the clue, “An early version of this novel was first published as a serial under the title ‘The Year 1805.’ “
All three contestants guessed wrong, with the answer being Leo Tolstoy’s Napoleonic War tome, “War and Peace.” Mr. Ruiz guessed “Great Expectations,” a Charles Dickens novel. Fortunately for him, he only bet $413, allowing him to advance.
The next day, Mr. Ruiz was far enough ahead going into Final Jeopardy that the other contestants could not catch up, securing himself a third day on the show by default.
On his third appearance, the opposite was true: Mr. Ruiz’s $12,000 was not enough to catch the leader going into Final Jeopardy. In the end, Mr. Ruiz made $35,987 through his two wins, and $3,000 for his finish on the third day.
Back in Montauk, there was a watch party for Mr. Ruiz’s first appearance on the game show. Organizing subsequent parties was difficult, though, since he was not allowed to say whether he won or not until the show aired. Nonetheless, he convinced some to come out again.
“I’ve had people coming up to me and congratulating me, everyone’s been so supportive,” he said. “That’s what I love about Montauk. It’s such a great community. I’m really seeing it to another level now.”
