Putting The "Fun!" In "Your March Madness Bracket Is Fundamentally Flawed And Will Not Win"

It is the tourney chaos we seek, the weird rides with weird teams.
You have filled out your brackets, and so have I. So has everyone else, just like we always do. You have your methods and I have mine, and if 400 consecutive years of losing my NCAA tourney pool has taught me anything, it’s that it is far more fun to not-win via unwise, exotic, pipe-dream picks than to not-win through safer, more conventional routes. Those traditional, bland routes are boring and dumb, really. They are the Big Bang Theory of March Madness, and I have no use for them anymore.

You are not-winning your pool and so am I, no matter what we do or don’t do or how much thought we put into it. We are not naïve. Our brackets are doomed to evaporate into forgotten clouds of negligence well before the Final Four. It is only a matter of when.

Sometimes it’s in the first six hours of the tourney, on an otherwise fine Thursday at Kilroy’s. The rest of the time, it’s in the Sweet Sixteen, in the cold, uncaring darkness of night. The most I can ask for, I’ve realized, is a few fleeting moments of intrigue before my inevitable exit. My “winnings” are now nothing but the mere chance to bask in the sweet, sweet glow of basketball savant-ness, if only for a minute or two, or frequently less than that, before it all washes away into the abyss of common sense and the status quo. In terms of the bracket, I am in the business of mere possibilities—maybe Eastern Mount Hilljack A&M really CAN take down Kansas, just as I brilliantly foretold!—and business is not real great, frankly. But so be it.

Those brief, rare instances where I picked 73rd-seeded Southwest Montana Tech–Phillipsburg or whatever to upset Kentucky and holy hell, it looks like it might actually be happening?! That is great fun, even when it doesn’t happen in the end. That is how God feels when He almost picks an upset, I bet! It is addicting and exciting and not terribly ideal for my health, and it’s exactly what the NCAA has been pushing into our veins for decades now: those wild, improbable upsets—or, more likely, the meager chance thereof. It’s the chaos we seek, the weird rides with weird teams with a one-legged coach and a Pittsnoggle for a power forward.

“March Prudent Rationality,” after all, would ring poorly in the ears of Americans after a long winter.

Look at it this way. Coca-Cola will not be running ads this week featuring some random Texas/Florida State first-round game from 1996 that no one remembers, where the 8th-seeded Longhorns held off the 9th-seeded Seminoles 73 to 65. Nobody is buying that drug. They’re not buying because nobody is selling, and for good reason.

No, the Powers That Are will be selling quite a bit of Bryce Drew’s dagger and R.J. Hunter’s jumper because Valparaiso and Georgia State. Because one was a 13 seed, the other a 14, and some lucky bastards picked those in their brackets and are STILL flying high.

That is why my 2017 brackets are laced with poor basketball decisions soaked in ether. That is why I have UNC Wilmington in the Sweet 16 and Iona beating Oregon. That’s why I have Florida Gulf Coast University—an online poker site run from a seedy beachside massage parlor—going to the Elite 8. (I desperately want to ride that particular dragon again.) None of these things will happen, of course. But who cares? There will be short-lived bursts where it’ll look as though one of them might maybe won’t seem so implausible, and that is all I can ask for.

We are not winning our bracket pools, you and I. May as well not-win while also basking in the glory of calling glass on a 45-footer.

Enjoy the games, everyone.