Filling out an NCAA tournament bracket is the perfect metaphor for life because it affords us the opportunity to make the same mistakes over and over and over again. Like those marks who pick Gonzaga to go to the Final Four every year because they’re “due”, we never break the cycle because we can never acknowledge the fault is not in our stars but in ourselves – our passions, our prejudices, our inability to behold the entire thing as the crapshoot it is. Once a year, like clockwork during the third week of March, millions of Americans mechanically pour their hard-earned wages into NCAA tournament pools they have virtually no chance of winning.

I know because I’m one of them.

But not everybody has a tourney pool horror story as gruesome as mine. A $24,400 horror story to be precise.

For more than a decade, I’ve entered a contest run by a friend of a friend in my hometown of Philadelphia. The organizer of the pool is named Tommy Martin*, who started it 22 years ago as a middle-school student. It’s ballooned through the years thanks to word of mouth and PayPal, with entries coming in from throughout the country. To this day, Martin runs the pool for fun and not for profit, taking three free entries for his trouble. (Though he’s quick to note he’s never come close to winning.) Overwhelmed by the logistical duties of managing such a large pool, Tommy has attempted to curtail its exponential growth by raising the entry fee – from $20 to $30 to $40.

In 2008, despite a lofty $50 buy-in, Martin Madness ballooned to 958 entries – bringing the total pot to an eyebrow-raising $48,800. Playing the efficiency numbers, my then-girlfriend and I went conservative and picked each No1 seed to advance to the Final Four, with Memphis defeating Kansas in the national title game.

I’ve always enjoyed the Martin Madness pool because of the astronomical numbers at play. The mere prospect of a five-figure payoff makes the tournament a worthwhile obsession long after your rooting interest has been eliminated. In a bad year – like my Stanford-Gonzaga national title game in 2004 – your dreams are dashed almost before the tourney begins. In a good year, your Final Four picks survive the first weekend and the rush lasts a good week-and-a-half before your pool’s inevitable self-immolation.

But this year was different. Aside from some early turbulence – we missed the Davidson and San Diego upsets during the subregionals – our chalk-heavy pool was unusually healthy. Hitting one result after another, our entry (“Be The Dream”, an unabashed John Chaney tribute) moved steadily up the table as Madness gave way to Sweetness. When the Elite Eight came around, we found ourselves with a puncher’s chance at the grand prize.

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We could hardly believe our good fortune when, for the first time in history, each of the four No1 seeds made the Final Four. With just three games remaining, we had a legitimate chance of bringing home first place in Martin Madness – a previously inconceivable accomplishment. When Memphis knocked off UCLA and Kansas steamrolled North Carolina on Saturday night, we moved into first place with one game left.

The following day – as visions of financial security danced through our heads – I’d just bitten into a slice of Bleecker Street Pizza when an unfamiliar 212 number rang through my phone. The voice on the other end introduced himself as Greg, or, “the guy who would win the Martin Madness pool if Kansas wins tomorrow”. Turns out Greg, who seemed like a perfectly nice guy, looked up my information on the pool site and wanted to make a diplomatic, stress-alleviating offer: He was willing to split the $24,400 winner’s share – down the middle, no questions asked – regardless of which team won Monday night. That way, we’d each come away with a generous payday regardless of the outcome. I told him I’d call him back.

I talked it over with my better half and we came to the conclusion that we didn’t want to “screw with the vibe” of our miraculous run – whatever that even means – as if financial horse sense would somehow invite negative karmic consequences. As dumbfounding as this complete lapse of pragmatism seems in hindsight, it sounded like the perfectly appropriate decision at the time. I called Greg back Sunday night and told him thanks but no thanks.

Monday night. We sat down in our West Village apartment and watched the game in near silence. It went back and forth during the first half, with Kansas opening a 33-28 lead at the break. Inhaling a bottle of Merlot during halftime didn’t numb our nerves as hoped. Late in the game, Derrick Rose poured in eight straight points to put Memphis ahead 54-47. When Rose hit a three-pointer shortly after to put Memphis up 57-49 with 4min 06sec remaining, I stood up, paced nervously toward the window and – for the first time all night – felt a genuine sense of relief. This was actually happening.

Cut to TV timeout. My girlfriend – bless her heart – grabbed her MacBook and commenced shopping.

When they came back from the commercial break, we learned the officials had conferred instant replay, ruled Rose’s foot was on the three-point line, which it was, and deducted a point: Memphis 56-49 Kansas. (I’d spend the next six weeks bemoaning the arbitrary nature of video review. To wit, if the basket hadn’t occurred right before a TV timeout, would the refs had conferred the replay?) I immediately got that disgusting feeling in my stomach typically reserved for Philly sports teams in big moments.

No need to recount the gory details of the worst-botched endgame in title game history. It’s just a blur of missed front ends, Memphis turnovers and Kansas conversions. Mario’s Miracle, while devastating, was practically anticlimax. And after spending the previous nine days making a steady ascent up the top 10, we plummeted to 24th place and crashed out of the money.

I’d never seen my girlfriend cry like that, before or since, and my mind kept returning to Chekhov’s The Lottery Ticket and wondering whether things were ever going to be OK again. She cried herself to sleep and, more impressively, cried herself awake the next morning. Of course, over time, wounds healed. But the poor girl can’t even watch a Chicago Bulls game without hissing an expletive whenever the TV shows Rose calmly draining a foul shot.

The next year I told her we shouldn’t even bother entering Martin Madness because there was no way we’d defy the odds in consecutive years and make a serious challenge for first place. But sure enough, when the email for the 16th Martin Madness came through, I filled out an entry and sent it through – just as I have ever year since. Lather, rinse, repeat. The cycle remains unbroken. The fault indeed is not in our stars, but in ourselves.

* - Name changed to protect the organizer, whose annual enterprise is most certainly not for entertainment purposes.