Stevie Ruiz lives in the sunny, beachy eastern tip of Long Island in the hamlet of Montauk. He works as a server in a restaurant and, like many who make a living in the seasonal enclave, he earns most of his income during the warmer months.
Two years ago, he left a career as a front office manager because he could make more money waiting tables. It takes him just three days in the restaurant to make as much money as he used to make in two weeks at a hotel. But there was a major downside.
“The hotel provided housing,” he said. “The restaurant doesn’t.”
That, he said, is the norm in Montauk.
“A lot of restaurants out here don’t provide housing for front of house workers,” he said. “Housing is pretty limited and expensive and they want to make sure they have their kitchen staff taken care of. You can always find people to pick up server shifts here and there.”
Without housing from his employer, Mr. Ruiz, who is currently staying with a friend, has learned to hop from one living situation to another. For a few weeks during the winter, he stayed at his mother’s home in North Carolina, where he spent part of his childhood.
“I’m turning 37 this year and, you know, you see family less and less,” he said. “So it’s nice to spend time with mom. We watch ‘Jeopardy!’ together. We hang out, I’ll cook dinner — it’s been a nice thing.”
Last winter, he also found an unconventional way to make a little extra money. Instead of just watching “Jeopardy!,” he tried out for the quiz show. Mr. Ruiz not only made it on the air but he won. The very next night, he returned to defend his victory and won again. On his third night, he was finally outmatched but not before he’d won $38,987.
$250 a Week | Montauk
Stevie Ruiz, 36
Occupation: Restaurant server and entrepreneur
On keeping a secret: Mr. Ruiz filmed his episodes of “Jeopardy!” in October 2024, but they didn’t air until December. For two months, he couldn’t discuss the outcome of his participation in the competition. “I would be hanging with friends some nights, closing out the bars, and close friends were like, ‘Come on, you can tell us what happened.’ I had to keep it quiet for two months and somehow I did.”
On passion projects: Cooking and design are Mr. Ruiz’s primary interests. He started Yotte’s, a Haitian cuisine pop-up. “I hope to one day be able to do a restaurant, but for now it’s a passion project,” he said. He also started Montauk Vice, the beginnings of a clothing line with a crew neck sweatshirt and a hoodie. “The first run sold out. I have some new designs I’m going to be putting out, and then do a reprint of the original run.”
Mr. Ruiz’s success on the show was a long time in the making. He started answering along with the on-air contestants by the time he was five. “My mom and grandma looked at me like, ‘What just happened?’” he recalled.
As he grew older, a refrain developed and he heard it from friends, classmates, and co-workers who watched him excel in various trivia contests: “You need to go on ‘Jeopardy!’”
In 2018, he took an online test — the first step to getting on the show. He took the test seven years in a row. Each time, he was told he would be contacted if he was advancing to the next round, and every year passed without receiving a message. But after he took the test last year, something new caught his eye.
“At the end of the test,” he said, “it tells you to whitelist certain emails so that the messages don’t go to your spam. I hadn’t seen that before. And I thought, ‘Wouldn’t it be crazy if they’d emailed me before and I didn’t see it?’”
Mr. Ruiz decided to search his inbox, and sure enough, he found a message that had been sent in 2021.
He emailed back, apologizing for the three-year delay, and received an invitation to complete the audition process, which eventually led to his appearance on the show.
A few days after he won two rounds of competition, Mr. Ruiz was invited to compete in a championship “wild card” round, which aired in January. He didn’t win but still came out on top.
“On your original run, you have to cover your own flight and hotel,” he said. “But if you go back for the championship, you get flight, hotel and a per diem. And I still got $5,000 losing in the first round so it was actually a $5,000 paid vacation.”
His success on “Jeopardy!” provided a welcomed, if short-lived, distraction from the reality that greeted him when the adventure wrapped: Mr. Ruiz once again needed housing before work restarted in the spring. “Not being provided housing has really, really been a challenge,” he said.
He started looking for a place in late January. Knowing that the game show windfall wouldn’t last forever, he set his maximum for rent at $2,000.
“And that’s not for an apartment,” he said. “That’s just for a room in a house.”
Mr. Ruiz said that available apartments are a rare find in an area dominated by single-family homes. According to Zillow, the median rent for a house in Montauk is $30,000 a month. Renting a room in a house is his best option, but many of the listings he’s come across are around $4,000 a month, he said.
With every option beyond his budget, he’s still looking, as he works through the long shifts of the high season.
One complicating factor is that affordable options are rarely found on the open market. More digging is always required.
“In terms of getting things that are remotely reasonable, it’s mostly through word-of-mouth, off-market, private Facebook groups — that kind of thing,” he said. “But even there, the things I’m seeing are more like three, four thousand a month.”
Right now, a friend is charging him a modest rate, $250 a week, for a bedroom. Mr. Ruiz is eager to avoid overstaying.
“I have a couple leads and I’m waiting to hear back,” he said. “There are people I know who’ve been working out here for 20-plus years. Met their wives out here, had children out here who now can’t find housing. They’ve been looking for months, same as me.”
Even with the perpetual search for stable housing, Mr. Ruiz doesn’t want to leave Montauk.
“I love this place,” he said. “When I was on ‘Jeopardy!,’ the way that everybody showed up for me and came to watch parties, it’s been great.”
He added, “I would never call myself a local, because I’m not from Montauk, I wasn’t born here. But, you know, I’ve been embraced by the community, which is something that I really do love and appreciate. Just to be able to go out anywhere and know there’s going to be friends there.”
The post To Afford Montauk, He Went on ‘Jeopardy!’ appeared first on New York Times.
