I won big on “Jeopardy!” So why does it still haunt me?

It was an early evening in the summer of 2019. I’d arrived at LAX with hours to go until my red-eye to Louisville. But even though I had plenty of time, I moved through the airport like a heat-seeking missile — past check-in, through security, down the long hall to my terminal. I found my gate, then kept walking, past the stores and the restaurants, looking desperately for somewhere to be alone. Finally, one terminal over, I found a quiet stretch of unused gates. I scanned the area so I could be sure that no one would hear what I was about to say. Then I pulled out my phone.

My wife picked up on the first ring. “How did it go?”

Once more, I looked over both shoulders with all the subtlety of a six-year-old pretending to be in the CIA.

“I won three games.” I heard her gasp. And then the grand total: “Honey… I just made $86,000.”

We talked for a few more minutes before she had to get back to rehearsal. I swore her to secrecy until my episodes could air. Then I spent the next few hours alone with my thoughts, ambling around the airport in a surreal state of bliss.

It had been a perfect day — the day I became a “Jeopardy!” champion.

It wasn’t until I got home that I started having trouble sleeping.

* * *

At first, the insomnia made sense. I was exhausted from my travels and coming down from one hell of an adrenaline high. It took me just under six months to go from online test to in-person audition to the set of America’s Favorite Quiz Show. I got to shake hands with Alex Trebek, a TV legend working valiantly through what would be his final season. I even got to tease Alex about his habit of saying “Good for you!” to wrap up a contestant interview, something I vowed I would bring up if given the chance. I had made more money in six hours than I’d ever made in a year. Lying in the dark, only sort of trying to sleep, I kept smiling at the sheer improbability of it all.

But when the second night came, I’d already moved on from my triumphs. Now my mind was stuck on game four, the game I lost.

I’d played well in that game — well enough to have a $4,200 lead when I hit the last Daily Double. The category was “Fictional Flags Flying.” I bet $4,000. The clue appeared, something about a submarine, the South Pole and a flag with the letter “N.” I had no idea. (“Who was Captain Nemo?”) My lead evaporated, and I fell back to the pack. I finished Double Jeopardy trailing by $1,400, and Andrew, a handsome journalist from Ottawa, got Final Jeopardy correct with a wager big enough to make anything I did immaterial.

We’ve all seen a game hinge on a moment like that. But those moments happened to other people. This one was all mine, and it cozied up to me in bed, forcing my brain to replay that clue on a loop. If I had just waited a little longer, could I have gotten from submarine to Captain, from “N” to Nemo? Should I have stood there until the last possible second, until Alex nudged me with a gentle “Steve?” Why did I bet so much on “Fictional Flags,” a category that could swerve in almost any direction?

Then there were all the downstream effects of my blunder to obsess about. In my last game, I didn’t even answer Final Jeopardy correctly — though I came close, writing the first two letters of “Steinbeck” before replacing them with “Camus.” Did this reassure me that I wouldn’t have won anyway? No. I told myself that if I had held onto the lead, surely I would have gone with my first instinct on Final. I would have coasted to victory. I would have been a four-day champion.

Why stop there? Why not think about the game after I lost, the one I stuck around to watch because I was still riding high, and I wasn’t ready for it all to be over. The Final Jeopardy clue in that game, in the category “Religion,” was one I could’ve answered since the age of ten. As trivia folks like to say, I knew it cold. But all three contestants got it wrong. So Captain Nemo was no longer the difference between a three-game and a four-game streak. He was the difference between three and five. And as any dedicated fan of “Jeopardy!” can tell you, five wins is the magic threshold. It’s the guaranteed ticket to the Tournament of Champions.

Adriana E. Ramírez writes about finding peace with losing on “Jeopardy!” in The Atlantic: “I came out stronger on the other side, and also a little humbler.” She wasn’t “crushed with embarrassment” when she watched herself lose — in a game like “Jeopardy!” everyone loses eventually, she points out, and there’s no shame in that.

During the day, when I had things to do and people to talk to, I was similarly upbeat. Sanguine, even. But in the middle of the night, the what-ifs would come back around: Why had I bet so much on Fictional Flags? And why the hell did I stay and watch that last game?! Even though I knew it was irrational, I had gotten stuck in a loop of self-doubt, incapable of appreciating my good fortune.

By the time my episodes aired, I’d received an invite to the Facebook group Jeopardy! Contestants, an ever-growing forum open to anyone who’s appeared on the show. As you’d expect, the page is full of nerdy humor, good-natured memories, and debates about last night’s episode. But occasionally, a group member will express a specific lament — a category they’d failed to study for, or the lunch break that halted their winning streak, or the dreaded buzzer that locked them out when it mattered most.

The first time I read one of those laments, it stood out like a neon sign. Here was a fellow traveler, a contestant who had also walked the path of game-show regret. Following up on a hunch, I called my friend Ben, who’d competed in the Teen Tournament in the ’90s. I asked him if there was anything about his experience on “Jeopardy!” that haunted him. Ben’s very next words were the clue that kept him from advancing to the Tournament final. Twenty-five years later, he still knew it verbatim.

* * *

How can I capture the deep strangeness of appearing on “Jeopardy!”? You step into an actual, physical environment you’ve visited hundreds of times, but never in person. The space feels more intimate than it looks on TV. The big board remains formidable. When I first walked into the studio, I felt like I’d teleported inside a movie. I’ve spent my career in theatre, so I’m comfortable with the difference between illusion and reality. But this place was on another level.

So there you are, soaking in the grandeur of the gorgeous set. You haven’t even competed yet, and somehow everyone knows your name. The entire staff is fantastic. You’re just eager to play, but first, there’s orientation, buzzer practice, camera setups. You don’t realize that the downtime is a blessing, because once the games start, things accelerate at an alarming pace.

“Jeopardy!” shoots five episodes, a full week’s worth, in one day. The gameplay moves so fast that I forgot much of what actually happened. When I watched my episodes two months later, I would say to my wife, “Oh, this question I got right,” only to see someone else ring in with the correct response. “Jeopardy!” time is weird.

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That sense of acceleration permeates everything, including the definition of success. I feel safe in saying that, for pretty much every “Jeopardy!” contestant, simply getting on the show is an accomplishment. But whatever any of us did right to get that far, well, every other contestant did too. It can be legitimately shocking to see a champ crush it in one game, only to go down 40 minutes later. But that simply illustrates how the show works — no matter what happens, there are always two smart people going home.

I recently polled a group of former champions about what they were hoping going into their first games. The results were refreshingly humble:

I wanted to get at least one question right.

I wanted to make it to Final Jeopardy.

I wanted to avoid becoming a meme.

Perhaps they were just being modest. I thought it’d be great to win one game and something like $15,000. But I certainly didn’t think it would be easy, or even likely.

The funny thing is, when I reached that goal, I had no time to bask in my achievement. There are only 15 minutes between shows, just enough to fit in a wardrobe change, a bathroom break and a rapidly guzzled Diet Coke. The nonstop momentum almost certainly helps the returning champion. But the main thing I was feeling was more, please. More winning, sure — but also more trivia, more buzzing in, more dramatic wagers, more interviews with Alex… more Jeopardy! I went from happy to be here to drunk on success in just under three hours.

And then, after three delirious victories, I lost. I keep wanting to compare the experience to professional athletics. You know, the minor leaguer who finally makes it to The Show and all that. But that analogy doesn’t work, because no sport is designed to retire its players the first time they lose a game. Even the most accursed teams have next season. “Jeopardy!,” on the other hand, is a single-elimination affair.

The sports analogy does feel apt, however, in one aspect — how “Jeopardy!” is constructed. There are four points of maximum drama — three Daily Doubles and the Final Jeopardy round. In these four, the right wager can provide a path to victory. The wrong one can wreck your game entirely. And you never know if the clue is going to be child’s play or hopelessly obscure. These moments are why Merv Griffin called the game “Jeopardy!” in the first place.

A game where both triumph and disaster are traced to specific turning points makes for fantastic television. But for the participants, it can mess with your mind. What are you supposed to do with the feeling that one moment was the difference between the universe you’re living in and an alternate one — a universe where everything’s just a little bit better?

* * *

As it turned out, I did play “Jeopardy!” one last time. Because of a bizarre and tragic confluence of events — a pandemic-shortened TV season; a returning champ’s travel restrictions; and worst of all, the death of a bright young man named Brayden Smith — I found myself invited to the 2021 Tournament of Champions.

The game itself was forgettable, at least on my end. It was a tough board, against stiff competition, with no safe categories for me. The one lesson I could have applied from my previous loss — take all the time you can on a Daily Double — I forgot when it mattered. But it wouldn’t have made a difference. I played tight the whole game, distracted by how sticky my hand sanitizer was as I gripped the buzzer. And I felt weird about being there at all under such awful circumstances. At least I got the Final Jeopardy clue correct.

Once I’d lost, I knew the sleepless nights wouldn’t be a problem this time around. When you make as many errors as I did, punishing yourself over a bonehead response is like a baseball team saying, “We would have won if the other team hadn’t hit all those home runs.” It wasn’t meant to be. Disappointing, yes, but at least I went down in flames.

Instead, I got to focus on the best part of the trip — becoming friends with the other champs. For three days, we ate tacos on an open-air patio in Culver City and swapped stories about life in our different pockets of the country. Everyone was just as thoughtful and genuine as I had hoped. We all still share a group text, and every few months we meet up online for trivia night. I’m told this bond happens with every Tournament cohort, but that doesn’t make it less special. And we do share something unique — we were Alex’s last group of champions.

I don’t stay up late thinking about “Jeopardy!” anymore. But every now and then, when I’m by myself and the house is quiet, my mind will conjure that other universe – the one where I won five games and an extra $30,000. In that timeline, am I more confident in my status as a former champ? Or am I just cursing myself for how I lost game six?

Then sometimes I think about a late night 25 years ago, in suburban Maryland, when I was driving my parents’ car on the Baltimore Beltway and headed down the ramp onto 295 way too fast. I skidded across three lanes into the grassy median on the other side, spinning 180 degrees and blowing out a tire. If it hadn’t been the middle of the night — if there had been anyone on the road at all – I’d probably have killed someone.

Another alternate universe, one born from actual danger rather than simulated jeopardy. The car crash would have been devastating. Winning another game and a bigger cash prize wouldn’t have changed much. Why, then, do both moments feel precarious? Perhaps we’re always veering close to the edge of some other life — and it’s only when we notice that it haunts us.