Winners & Losers: Confessions of a March Madness Nit

People bet sports for all kinds of reasons. Many are in it for the action. Some are bored and can’t figure out what the hell to do with their money.

A fraction of gamblers are actually astute. They study stats the way rabbis study the Talmud and place wagers to make a living or to supplement money earned elsewhere. But it’s not easy.

The precarious nature of sports betting, even at the best online sportsbooks, is underscored by the thin line between being a winner and being a loser. Ace 50 percent of your wagers and, factoring in the vig, you can go broke. Win 55 percent of the time and, pending a large enough bankroll, you can become a millionaire. Most people fall into the former category.

As for myself, I am not aiming to go broke or to win millions. I’m just looking to be engaged in the games and have something to banter about with a few relatives, my wife, and the once notorious Hollywood madame Heidi Fleiss.

When it comes to gambling, my relatives do their own thing and make out okay (as I am told). As for the rest of us, we rely on betting advice from professional gambler Alan Boston.

He’s kind to share a few picks with us for each set of games, and it’s always a bit of a roller coaster. But, for me, that’s kind of the point.

If I didn’t have a little money on the matches, I wouldn’t bother watching them. Instead, with a trivial sum at risk, I spent last night on the edge of my seat, hoping for Alabama to beat North Carolina.

They did! In the process, though, texts were exchanged, balls were busted, opinions were shared – no matter how wrongheaded they might be. That’s what draws me into March Madness betting: the social component.

March Madness betting
Image credit: Tim Gerland/Flickr

Normally, I hate when people ask me who I’m rooting for during a big game weekend or whether I like the Giants or the Jets. Usually, I lack much of an answer.

I don’t care about sports unless there is something on the line and I don’t know enough about the games to make intelligent decisions. So, therein, resides the rub. I’m not a fan of random gambling. It’s just not fun for me to bet on things without having at least a perceived edge.

During football season, I cadge picks off of Bill “Krackman” Krackomberger. Last season was a net win. During March Madness, at the urging of Heidi, it’s Boston who operates as the gambling sherpa. We believe he will lead us through the perilous heights of college basketball championships.

So, how is it all going? I am in the hole for a grand total of $115. If Marquette wins tonight, I’ll be closing in on even. Yes, I know, I am a pathetically low roller and a nit to boot. But all that is okay. I’ll be texting, commiserating, and rooting for colleges that I could not come close to pinpointing on a map. Win, lose, or draw, I’m paying a small tax for the fun of it all.

Go Boston! Go Marquette! Go Kaplan!

Michael Kaplan
Gambling Author and Journalist

Michael Kaplan is a journalist based in New York City joined Techopedia in November 2023. He is the author of five books ("The Advantage Players" comes out in 2024) and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling and business — with a particular interest in spots where all three intersect. His article on Kelly "Baccarat Machine" Sun and Phil Ivey is in development as a feature film.