This article is part of Upstream, The Daily Wire’s new home for culture and lifestyle. Real human insight and human stories — from our featured writers to you. *** My trivia team, Post Trebek Stress Disorder, just won the first-ever “Jeopardy!” Bar Trivia League. It might seem like a team made up entirely of former “Jeopardy!” contestants (whose deep bench includes several three-time “Jeopardy!” winners, some of whom didn’t come out to play during the course of the Bar Trivia League) would automatically be the front-runner in a bar trivia contest. But we were weren’t. It felt like we were underdogs the entire time, and we had to overcome several tremendous obstacles to win the whole thing. At least in our minds, we were the Little Trivia Team That Could. I started PTSD in 2013 after I won three games of “Jeopardy!” and couldn’t let go of the afterglow. One other guy, Jared Hall, who lived in Austin and had recently won six games, was my co-founder. The rule quickly became that in order to play on our team, you had to have at least appeared on “Jeopardy!” once. So whenever someone from Austin showed up on my TV, I found them on social media and asked them to join. Not everyone said yes, but those who did soon found themselves belonging to what a 2017 Texas Monthly article called “The Best Little Trivia Team In Texas.” But in recent years, PTSD had faded. The desire to answer questions while drinking cider still burned in me, but other teammates had moved out of town, lost interest, had families, or, in a couple of extremely sad cases, passed away. Then in the summer of 2024, my teammates Kate, Cecily, and I got the call to appear on “Pop Culture Jeopardy!,” a new “Jeopardy!” variant that was airing on Amazon Prime (though is now on Netflix, where people actually watch it). Our team lost, but it turns out that Jessica, one of the women who barely beat us, also lives in Austin and, in fact, had been one of my prospective PTSD recruits after she won three games. But her episodes aired in March of 2020, a time when everyone kind of lost track of reality for a couple of years.  Jessica was such a good trivia player that I said to myself, “I’m never playing against her again.” Instead of avoiding her entirely, which wasn’t an option, I re-upped my invitation to play with us. She was down, which was very fortunate because she proved to be the secret sauce that would bring my wavering trivia team back to life. She was not only the perfect teammate but also a co-captain and partner with whom I could trust my trivia team’s legacy. When “Jeopardy!” announced the Bar Trivia League, she was, as always, into it.  And so Jess and I set forth to slay the trivia dragon. It wasn’t always just the two of us, though sometimes it was. Occasionally, guest stars would join. Her husband came out one night, and my wife came out another night, to enjoy the drinks and encourage us as we engaged in our dorky mental athletics. For two games, the most important two of the season, I stacked the box with a full team of six former “Jeopardy!” contestants, and it’s a good thing I did — because we needed to get every one of those answers right.  Our first week, we played conservatively, probably too conservatively, but it’s a good thing we did because the Final Jeopardy! question was a stumper about an obscure cable company (Optimum), and if we’d bet too aggressively, our league would have been over before it started. After that, the strategy became clear. Though you receive five points for a league win, teams were playing all over the country, and not directly against us on any given night, so total points earned serve as the tiebreaker. You need to bet all your points every time a Daily Double hits.  Unlike in regular “Jeopardy!,” in the bar league every team gets a chance to answer every question, so you see scores in the hundreds of thousands that would never be possible in a regular “Jeopardy!” game. For the next four weeks, we scored more than 300,000 points a game, except for one off week where we scored 252,000 points. One week, we scored more than 388,000 points. But this strategy also has its risky side; if we missed a big Daily Double question, we’d zero out our scoreboard. Like a slugger swinging for the fences on every pitch, there was a chance for a big whiff that would cost us the title.  By week two, there were already only 31 undefeated teams left in the country. That number cut in half the next week. After week five, there were eight, and we were one of them. However, there was another team in Austin, also comprised of several former “Jeopardy!” contestants, that remained undefeated. I had a bitter personal conflict with them, as I chronicled in an article at my previous employer. Jess, who’s friends with everybody, continued to hang out with them. But at their regular Wednesday night trivia gig, they basically avoided her and spoke around her in whispers.  The other team had found a loophole. You can only play JBL under your official team name one night a week. But since the games change every day, you can play multiple times a week under a pseudonym. This occurred to me early on, and I proposed to Jess that we occasionally invoke the Assassin’s Creed and try to do that to take out rivals. But she said that would be unsportsmanlike and uncool. So I allowed my co-captain to guide my conscience like Jiminy Cricket.  Our rivals, desperate for victory, had no such compunction. On that Thursday night at the Via 313 pizzeria near the University of Texas, they snuck in right before the game started at 7. They might as well have thrown down the glove. They’d come to take us out.  Unluckily for them, a new ringer had appeared on our team, a guy named Caleb who just two weeks earlier had fought “Jeopardy!” super-champion Jamie Ding to the death and had lost. Fortunately for us, Caleb is engaged to a guy who’s a big professional wrestling fan, so he knew a WWE answer, “ladder match,” that our enemy team didn’t. And then, in Final Jeopardy!, we got the right answer (Ian Fleming), while they didn’t (John le Carré). When the host announced their wrong answer, our entire team laughed involuntarily, and our enemies slunk out of there ashamed. Demoralized, they lost their next game under their official team name and emailed Jess, wishing us good luck. One more obstacle removed.  By this point, we were down to six undefeated teams left in the country. PTSD stood well ahead of most of them, in second place. But there was a team in Flossmoor, Illinois, called “Bucket of Kneecaps,” that was a couple hundred thousand points ahead of us. We decided to play conservatively since catching them was basically impossible if they won out. Even if we didn’t win the national title, we could still win the Central South region, which would at least come with a thousand-dollar prize.  After an uninspiring week seven win, it seemed like second place was our destiny. But then I woke up on Wednesday morning of the last week of play to find out that Bucket of Kneecaps had lost. What I didn’t know then, but know now, is that a player from Washington, D.C., also a former “Jeopardy!” contestant, had traveled to Chicago specifically to take them out. Apparently, his team had finished second after a drunkenly bad Daily Double bet in week one, removing their chances at a national title. But he was determined to challenge whoever was left in the final week, because he wanted the league to have, as he later told me, a “worthy champion.”  This is apparently an extremely well-connected man because he put together two teams to challenge Bucket of Kneecaps at that bar in suburban Chicago. And he won. It turns out that Bucket of Kneecaps was just one man, apparently quite friendly with the trivia host and bar ownership. Let’s just say they all exchanged angry words after the game.  It won’t surprise you that this trivia ronin showed up at Via 313 in Austin the very next night, to test PTSD, which was now playing for the national title. And he gave us hell. We were in third place after round one. Early on in Double Jeopardy!, one of our teammates, who’d been sitting quietly for weeks, pulled an answer about a question involving a pasta shape named after an Italian word for cake (tortellini). No one else in the bar got it right, and suddenly we were in first place.  At the end of the round, we remained in first, tied for points with another team that showed up every week to try and beat us. But we were ahead of them because Jess had been speed-typing our answers on her laptop all night. The final category was NOVELS, which I felt good about, and the final question involved a 24-hour live reading of a novel in New Bedford, Massachusetts. It was obvious pretty quickly that the answer was Moby Dick, and that was ballgame. We’d won the “Jeopardy!” Bar Trivia League.  As a prize, we get $1,000 for winning our region, plus a pizza party at the venue paid for by “Jeopardy!” In addition, everyone who played 50% of the games or more gets an all-expense-paid trip to LA, including airfare, hotel, a tour of the “Jeopardy!” studio, attendance at a “Jeopardy!” taping, and a meeting with “Jeopardy!” host Ken Jennings and “Jeopardy!” producers. The initial prize involved a “Jeopardy!” audition, but obviously, we don’t qualify for that. Three of us, Jess, Kate, and I, will gladly accept the prize and will head to LA whenever the call comes. This may seem like an ironic reward for a team comprised of former “Jeopardy!” contestants, but I have a plan. When I appeared on “Jeopardy!” in the Paleolithic year of 2013, it was a very different show. Once your run was done, you didn’t get to appear again unless you’d qualified for the Tournament of Champions. But the rules have changed, and there are many different levels of tournaments now. People who’ve won three games come back all the time. Contestants who won zero games get second chances, and in a few cases have advanced deep into tournaments and won hundreds of thousands of dollars. So, you know, why not us? There was no other chance on earth “Jeopardy!” would invite me, a guy who’d been on the show a decade and a half ago and had performed well but not exceptionally, back for another bite of the apple. For Jessica, who also appeared before the super-tournament era, the situation was the same. And Kate had never won at all, not finishing up her Final Jeopardy! answer in time despite the fact that she knew it, a fact that has haunted her for nearly a decade. I want redemption for myself and for two of my best friends in the world. The only way any of us were going to even have a prayer to get back on “Jeopardy!” was to claw our way up (with integrity and friendship) out of the bar-trivia pits, like Bruce Wayne in “The Dark Knight Rises.” And we did it. *** Neal Pollack, “the greatest living American writer,” is the author of 12 semi-bestselling books of fiction and nonfiction and is a three-time “Jeopardy!” champion.