A Gambler’s Love Letter To March Madness

It is hard to believe, now that I’m the overlord and poet laureate of a legitimately large NCAA Tournament bracket pool, that it was little more than a decade ago that I knew little and cared even less about this beautiful American phenomenon. A journalism fellowship brought me to the University of Michigan, some of my colleagues were doing a pool, and I’m always down for some inexpensive gambling. I think it cost $10, which may scientifically be a degenerate’s gateway price point.

Up until this, I ignored this whole part of the year with its “brackets” and “madness” and “Cinderellas” and that cloying power ballad that everyone wants played for them. I grew up on Long Island where we were taught, because there weren’t really any college teams of any significance, that professional sports were The Real Thing. Then I went to Northwestern, where our basketball team was so bad that in my freshman year, I received an invite to try out simply because I’m a 6-foot male. By the time I landed in Las Vegas as a reporter in 1996, UNLV’s magical runs had rotted into sordid scandal.

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2012: NCAA bracket breakthrough

But then it’s 2012, I’m on a study trip to Brazil and Argentina, and I’m tuning out a lecture on South American trade to figure out how I might win this thing. I don’t remember much about that tournament; the Internet tells me Kentucky beat Kansas, Michigan lost in the first round, Ohio State went to the Final Four. None of this was of much significance to me at the time.

What amazed me was the way this one form of gambling could really bond me with friends in a way no other type of betting ever would. Not even live poker games, which I love, create this much unity because, of course, most of the time you never even know what cards other people have. The closest I could recall was one year in ninth grade at Syosset High School when I participated in a fantasy baseball league run by a couple of classmates, but then my Mets became bad again so I stopped paying attention. Fantasy sports always felt like too much homework.

That March in 2012, though, my friends and I would talk all the time about the games, the possibilities and Byzantine pathways that could help us win if only these schools we’d never heard of could step up their three-point game. The prize might as well have been a gift certificate to Arby’s; I now understood the fuss.

The love only got deeper the next year when I could veg out in front of the TV throughout that first weekend of constant action while pretending to be “working from home.” Each game felt like a short story, narrated by booming voices who could catch you up on the personal dramas and season-long hijinks of each squad just enough to make the wild finish satisfying. Then you could just switch to another and another and another?!?

The most wonderful time of the year: March Madness

By 2014, I started my own NCAA bracket pool, which consisted of maybe a dozen friends and family, and began writing pithy daily summaries that mixed analysis of the games with cultural and personal observations. With the exception of 2016 when my father got suddenly very ill and died between the first and second weekends, and 2020 when COVID iced the whole thing, March Madness became my most wonderful time of the year.

This time around, we have 31 poolers with 42 entries, and the range of people who come together for this represents so many periods of my life. There are close friends I made as a Vegas podcaster in the Aughts. There are work colleagues from my stints as a Michigan fellow, at Politico, and now here at Playin USA. There are my nephews and their many, many buddies. There are spouses and in-laws of people who don’t care about basketball one bit. And occasionally someone random wanders in by accident on the app we use and, if they pay up, they’re welcome.

Plus, I introduced an innovation last year: I set aside one pool for “auto-fill” and make that the Communal Bracket. It’s always crazy – this year’s has Arkansas over Baylor in the Final – but at least it gives everyone a reason to stay engaged.

Brackets over bets

Perhaps the most interesting part of all this to me is how little I feel the need to bet on the individual games themselves because my itch to have some skin in the game is scratched by running and writing about our pool. The only wager I made the whole first weekend was taking Farleigh Dickinson +14 against Florida Atlantic and that was just because I found it bizarre that the line was predicting a blowout. It was a good bet.

I’m also intrigued by how little the whole advent of name, image, and likeness (NIL) has impacted any of this. The fears have been that student-athletes, now eligible to make big bucks while still in college, might become selfish on the court or more vainglorious to ramp up the attention they receive. Instead, the competition may actually be better because the kids can make money and stay in school longer.

You might be wondering how my bracket’s doing this year. Not so good. I had Baylor to win, and those Waco wackos failed me last night. Oh well. There’s always next March.