Powerful Life Lessons From a Six-Time Jeopardy Champion Who Lost it All

Powerful Life Lessons From a Six-Time Jeopardy Champion Who Lost it All

It felt like I was slamming headfirst into a brick wall over and over again. Each time I tried to respond, question after question, I came up empty. After a few minutes it stopped feeling so jarring. It just started to feel like karma.

I, a 24-year-old Jeopardy champion, was being dealt the same treatment that I had doled out to my 12 previous competitors.

Perhaps that’s the most poetic aspect of this great institution of televised trivia: It doesn’t matter how many times you win or how much cash you amass, your final exit from the Jeopardy stage is always slightly inglorious.  

Everyone — mega-champion or not — walks out of that studio a loser. There was a lesson in there somewhere. But I didn’t know it yet.

***

It was 3:45 p.m. on August 20, and I was standing where millions of people only dream of standing: behind the returning champion’s podium on the Jeopardy sound stage in Los Angeles, playing — and winning — America’s favorite quiz show. I was in the middle of my fifth straight game of the day (my seventh game overall), and everything was going smoothly.

By 3:55 p.m., things had started to turn sour. My timing was way off; my mind was growing cloudy. My legs were starting to ache. 

I would read the category — “Writing Teams,” for example. I would read the clue — “Glass Town is an imaginary place in the early collaborations of this famous trio of sisters.” I would come up with my response before Alex finished reading the clue — the Brontës, of course. I would do a split second confidence check of my response to make sure I felt comfortable buzzing in. I would prime my thumb, careful not to buzz in too early and risk being locked out. I would wait for precisely the right second, attuning myself to the crisp cadence of Alex’s voice and then mash down on the black plastic signaling device that was nestled snugly in my sweaty palm, clicking away repeatedly with my thumb.

And then, I would slam into a brick wall. My competitor would ring in before me with the right answer. Alex would give him a pleased nod, or smoothly say, “That’s right,” or give him an emphatic “Yes!”

Stuff that he used to say to me

I found myself in a distant third place and reality quickly sunk in: I was losing on Jeopardy. To put a finer point on it: I was getting my ass kicked on Jeopardy. For the very first time.  

*** 

I finally became a Jeopardy loser after winning six straight episodes, the last two episodes of season 29 and the first four episodes of Jeopardy’s 30th anniversary season. Across my six wins, I amassed a total of $181,001, high enough to secure a spot as #9 on the all-time Jeopardy winners list. I succeeded beyond all my expectations.

For most Americans, Jeopardy is an abstraction, just another element of the late 20th and early-21st  century pop culture background noise. You catch a game here and there, ask jokingly what happened to Trebek’s mustache, and maybe talk about it with your grandmother.

But for some people (read: total nerds), Jeopardy is more than just a frustrating quiz show. It’s a goal. It’s a destination. It’s a lifestyle.  

My journey towards the Jeopardy lifestyle began many years ago, but the most recent chapter in the saga opens on March 28, 2012. On that day, I, along with 100,000 other hopefuls nationwide, took the Jeopardy online test: a timed series of 50 trivia questions. I scored well enough (I’d guess I got 45 out of 50 correct) to qualify for an audition that August in New Orleans. My favorite question came in the “Before and After” category, which requires a response that is a combination of the two names hinted in the clue: “He sang ‘Like a rolling stone’ and wrote ‘A Child's Christmas in Wales.’”

Correct response? Who is … Bob Dylan Thomas, everyone’s favorite Welsh singer-songwriter.  

It was at my audition in New Orleans that I first came into contact with kindred souls. We were all intelligent, we were all strivers, and we were all slightly too obsessed with Jeopardy. After 50 more trivia questions, a brief simulated game of Jeopardy, and a quick chat with the irrepressibly peppy contestant coordinators, we were told that if we performed well enough they could ask us to appear on the show at any point over the next 18 months. As I strolled the French Quarter that afternoon, I felt confident that sometime, somehow, I’d be a Jeopardy contestant. 

***

Seven months later, as I found myself cruising north toward Interstate 10 from Big Bend National Park, way out in the “Big Empty” of West Texas, thoughts of Jeopardy glory were far from my mind.

My girlfriend and I sped along a narrow strip of two-lane highway, crested a hill, and began to descend into the tiny town of Alpine. Though remote, this high desert outpost welcomed us with open arms and full cell phone service. It was the first time in days I’d been able to get a signal — even a single bar of service is scarce in the vast, otherworldly expanses of West Texas. I glanced down at my phone and noticed a voicemail. I recognized the 310 area code immediately: Los Angeles. Culver City, to be exact — the home of Sony Studios.

I knew what the message said before I even listened to it: In about a month, I’d be answering trivia questions in front of camera, proving my smarts (or my stupids) for an audience of millions.

I had some serious work to do.

Two days after receiving the call, I emerged from the library into the searing Austin sun, my arms laden with a stack of reference books. Classical music, sports, mythology, cinema, the Bible. I cast a wide net.

As I walked toward my car, I could hear the Jeopardy theme music playing in my head. In just a few weeks, I’d be standing on stage as that music played. I could hear announcer Johnny Gilbert intoning those immortal words: “THIS IS JEOPARDY!” He’d introduce Alex, my competitors, and then me. I imagined myself trying to look cool for the cameras. I imagined myself failing.

For the next month, I neglected work, school, and my personal life to hone my Jeopardy skills (fortunately, the world forgives you for this kind of stuff when you’re 23).  

I quickly settled on a grand strategy: Jeopardy contestants keep playing until they lose, and knowing that I’d be appearing on one of the last five episodes of Season 29, I made it my goal to win the very last episode of the season. That would allow me to take the entire summer to prepare for my return to the Jeopardy stage for the first episode of Season 30.

I found myself quickly getting accustomed to the Jeopardy lifestyle: studying on the bus, studying during class, studying on my lunch break, and then coming home to watch a full hour of Jeopardy before dinner. I put myself to sleep each night by reciting the U.S. presidents in order, backwards and forwards. The voice in my head started to sound like a wise, good-natured Canadian septuagenarian. I kept roughly 10 Wikipedia tabs open in Google Chrome for the entire month.

I was obsessed. 

***

(Photo by Debbie Garcia, Daily Texan)

In mid-April, after four weeks of ceaseless preparation, I found myself standing outside Jeopardy’s soundstage, hidden within the sprawling Sony Studios lot in Culver City. I had reached the promise land, and it was just as magnificent as I had imagined.

Jeopardy tapes five episodes in a day (sorry to ruin the TV magic for you), and I had to sit through the first three in the audience. Apprehensive but trying to keep it cool, I bided my time as my fellow contestants played valiantly in front of the cameras. They fell one by one, vanquished by insanely tough questions, bad wagers, or a lack of buzzer mojo. The contestant herd thinned after each game, until my name was finally called.

There I stood behind my podium, shakily grasping my buzzer, trying to appear confident and self-assured. I didn’t want to look petrified on national television. I smoothed my suit jacket and adjusted my shirt collar — both chosen in close consultation with my mom and my girlfriend — silently hoping that my clean, contemporary look would set me apart from the average Jeopardy contestant.

I heard the stage manager call the 10-second countdown. The theme music started playing. And then Johnny Gilbert, the voice of the show for 30 years, began his announcement:

“THIS IS JEOPARDY!”

The moment I had been hurtling toward had finally arrived. The nerves, the self-doubt, and the anxiety all melted away. I didn’t feel much after that point. I was ready to play.

To say that the next couple hours were a blur would be an understatement. It’s difficult to describe exactly what it feels like to be up on that stage, playing the game, but it’s the closest I’ve ever gotten to truly feeling “in the zone.” I’ve told people it’s a Zen-like state, but I’m not sure if that clarifies things. Perhaps this is the best way to describe it: When I was really rolling, it just felt like Alex and I were having a conversation together. Call and response.

I got off to a solid start in my first game, taking control of the board pretty early. I locked into a good rhythm and by the time the second round was finished, I had more than doubled my opponents’ scores; no one could catch me. And just like that, I was a champion.

My second game was more competitive, but I pulled out the win nonetheless. I knew the Final Jeopardy correct response, “Who is Van Cliburn?” solely because of the studying I had done — a nice validation of my efforts. In two episodes, taped over the course of about 1.5 hours, I had won almost $60,000. I started to cross things off my mental checklist. Student loans? Almost paid off. New car? Maybe. Nice vacation? A definite possibility. And I wasn’t done yet.

Here’s a fun insider secret: As soon as you win an episode of Jeopardy, everyone in the studio starts referring to you as “champ.” The sound guy who adjusts your body mic says, “Nice work, champ.” You get a “Congrats, champ!” from the contestant coordinators. Even your fellow contestants will start to refer to you as “champ,” silently hoping that they will receive the same appellation soon. It’s a moniker I quickly and vainly learned to love.

My second win marked the final episode of Season 29, after which the entire show went on summer hiatus. The strategy that I had plotted out a month before had become a reality. The months ahead of me seemed daunting: Finish up graduate school, graduate, and find a job. Oh, and prepare for at least one more game of Jeopardy.

America’s favorite quiz show still held me in its grip. No escape from the Jeopardy lifestyle.

***

In the weeks immediately following my first Jeopardy tape date, I gave myself a break. I watched the show much less, I studied very little, I tried to think about it as seldom as possible. I didn’t want to burn myself out before my final preparation push.

There was also another practical matter that made me want to keep Jeopardy off my mind. I was a Jeopardy champion, but no one besides my girlfriend and very close family could know that. I had been contractually sworn to secrecy. I’d have to keep it all under wraps until late July, when the episodes were to air. So much for shouting, “Don’t you know I’m a Jeopardy champion?!” as a way to get quicker service at Starbucks. My friends, my coworkers, and random baristas would remain in the dark. It needed to be a surprise.

So I toiled away silently for the next three months, keeping my achievement quiet while preparing for my (hopefully) triumphal return. I tried to manage my expectations by telling myself that my two wins could have been a fluke. I could step back up on that stage and be greeted with a serious clobbering; there was no way to know. Embracing uncertainty, I quickly settled on a new goal: qualifying for the Jeopardy’s yearly Tournament of Champions (ToC). I was pretty close to qualifying for a spot in this all-out, televised trivia brawl, but needed at least one more solid win. 

***

In mid-August, I walked back into the Jeopardy studios in Los Angeles feeling confident.

“Welcome back, champ!” I heard as we strode onto the soundstage. I was reasonably certain that I could win at least one more episode, hopefully qualifying for the ToC in the process. Beyond that, however, I had no goals or expectations. I just wanted to play again. That’s one thing that isn’t always conveyed by the contestants’ strained visages and stilted responses on TV: Just playing is the coolest consolation prize in the world.

As the theme music swelled, Alex strode out onto the stage as Johnny Gilbert announced the first episode of Season 30. Thirty years. These two guys have been doing this and winning Emmys for it since before I was born. A humbling reminder.

My first game was a close one. Even though I was in the lead going into Final Jeopardy, my victory was far from assured. The final question, however, was an easy one. The category was “Poets” and the clue contained a reference to “Old Possum.” T.S. Eliot. We all got the correct response, but I wound up ahead, with $28,801. I was back.

I quickly got used to the routine: fall into Zen-like trance, win game, walk off stage, change clothes, have make-up retouched, put body mic back on, return to stage for the next game. Even when I was resting between episodes, I kept myself primed.

The questions kept coming and my wins began to accumulate. I said goodbye to a number of tremendously talented competitors. Here’s another secret of the Jeopardy experience: Regardless of the outcome, the frighteningly smart, outrageously dedicated people you meet will make it all worthwhile.

By the time I reached the fifth and final game of the day, it was about 4 p.m. I had been playing Jeopardy with a few breaks since 11 a.m. and had been at the studio since 8 a.m. My body and my mind had been in adrenaline-fueled overdrive for hours. I had never felt as simultaneously electrified and fatigued.

And so it was at about this time, after having won four straight games, after having been on my feet for what seemed like hours on end, that I saw myself barreling towards that unyielding wall. Exhaustion was setting in. I sensed it pretty quickly, and I expect my fellow contestants did, too. My massive yawns during lunch probably didn’t help. I tried to keep up my calm, cool exterior, but it was no use.

I would lose, miserably. I would be humbled on national television. I would be the champ no longer. 

At the end of my final game my total stood at $0. A more thorough drubbing has scarcely been seen on a game show. Feelings of relief, disappointment, shame, and pride washed over me in unison as I stood on the stage with Alex and my two competitors after the game.

***

My brief foray into the Jeopardy lifestyle was immensely rewarding — both intellectually and financially — but losing was painful. I soon realized, however, that losing is an essential component of that lifestyle. The inevitability of my eventual failure made everything that preceded it seem even more sublime. My highs on the show were very high. It was only fitting that my lows were equally low.

So I guess that’s the proverbial lesson in all of this. No matter how much you win, everyone’s a loser eventually. Losing so spectacularly didn’t feel great, but it felt right.

And it felt fair. 

(Be sure to read Jared's article "Insider Tips on How to Win Jeopardy.")