Winners & Losers: Let’s Hear It For The Lucky Guys Who Won Super Bowl Overtime Bets

Super Bowl overtime bets came off in 2024

When it comes to life, I can’t complain. I’ve had it pretty good and I’ve been pretty lucky. When it comes to gambling, I’ve never been able to bring myself to rely on luck.

This past weekend, with the Super Bowl going into overtime, it was the revenge of the lucky. They’re the ones who cleaned up by betting on the game to hit OT. It paid 10-1 for good reason; the betting odds of overtime happening were much longer than that. I made five wager on the big game. Of course, none of them were Super Bowl overtime bets.

A professional gambler, one who lives and dies by numbers, told me that he bet against overtime and wagered $23,000 to win $2,000. He did it because he knew that that the odds on his end really should have cost him 18-1; so that made it a good bet for him and a good bet for the bookies, but a terrible bet for those who took the other side.

Last weekend, for the second time in Super Bowl history, the other side came in on that wager. The sucker bet was a winning bet and it contributed to the leading online and offshore sportsbooks getting creamed. Same for the sharp bettors and so-called wise guys.

To be honest, I’m thrilled for the sucker side. They were happy to have won, but, more importantly, happy to have made the bet, even though, on the face of it, it was a terrible idea.

At one point, on the Monday after the game, I wanted to write about people who won from Super Bowl overtime bets. I called a couple buddies of mine, all of whom are sharp gamblers. Nobody knew anyone who made the bet. “It was all public money,” one told me. “Everyone I know bet the other side and lost.”

Another complained to me, “We got f**king killed. We all had to be carried out. It was the public’s day.”

Though I’ve written about gambling forever, the idea of random wagering – i.e., actual gambling – is anathema to me. I hated playing blackjack until I learned to card count.

Craps is the sort of thing I play if I must. Like if I am in Las Vegas or Atlantic City with guys who want to gamble. That leaves me needing to choose between ponying up cash and being comfortable losing or watching from the rail.

I invariably choose the former. Never mind that it’s hard for me to be happy when getting the worst of it – which usually makes me the dullest guy at the table, sticking to pass-line bets and taking odds, which is an even money wager.

Gambling for the public is fun and adrenaline producing. There is something to be said for that. Two weeks ago, I was doing a story about a poker game that takes place in a room above a Korean restaurant in Manhattan.

It was a cash game and I suck at cash-game poker but, conversely, I understand how to play tournaments and I do decently at that variation. I usually avoid cash, but, day of, the guy I was writing about sent me a one-line text: Bring money!

So, I’d be playing instead of just watching and reporting. Fine. I bought in, played cautiously, took some notes and was a complete nit, the tightest guy at the table. I won a bit, but I had the least amount of fun. Is that really a win? Probably not. It’s a bit like my tendency to bet unders in sporting events.

As a friend commented with unhidden disgust, “Where’s the enjoyment in that? Rooting for less to happen is the worst way to watch a football game.”

Of course, the overs tend to be tilted in the house’s favor, because the public loves betting on overs as much as they love taking favorites.

It reminded me that there is something to be said for not understanding a wager’s inner workings, for not caring whether or not you win, and to just be there for the kicks that come with raising in the dark and showing hands for the hell of it. Never mind if the move puts you at a disadvantage.

Then you embrace the action, decide to not care about getting the best of it and hope like hell to get lucky. You laugh at the nits, throw caution to the wind and know that it feels all the sweeter to cash in on a longshot that never should have come through in the first place. Whether at the gambling table or beyond, we all need to try it sometime.

That’s why I’m raising a glass to those crazy, lucky b******s who cashed in big on their Super Bowl overtime bets this past Sunday. I hope they’re blowing the money on things that are fun and ridiculous.

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.