Tough Questions: What’s the Most You’ve Ever Lost on a Bet?


Every Monday we ask everyone who hangs out around here to answer a tough question. This week:

What’s the Most You’ve Ever Lost on a Bet?

Rules are simple: we want to know, what’s the most you’ve ever lost… on a coin toss? Or anything, really. But that’s the line from the thing. You know, the thing?

It can be any kind of bet, but what did you put up that you can’t take back?

Alex Russell

I proposed this question this week because Vegas is on my mind. I go every year, but I am absolutely not “Vegas Guy.” It’s a rotten town that is wonderful in a very specific way, but I have a bad habit of giving back whatever I win before I leave. This trip I managed to double down and look really, really dumb as I did it at a blackjack table. It was impressive in a stupid sort of way, but that definitely could not last. I handed it all back half a day later in about five minutes. The $200-up, $200-down movement was awesome – in the actual definition of awesome. Maybe that’s not a lot of money, but it’s definitely quick.

Brent Hopkins

I am not really much of a gambler I (I am tight with money, as they say) so I don’t tend to lose anything monetary when I do choose to bet. I would say the biggest thing I have lost on a bet is my pride as a gamer, but that comes with being a blowhard and a highly competitive person.

Austin Duck

I don’t really bet money on things; I lost $10 in elementary school betting on the New England Patriots in a Super Bowl and, since then, eh. Not for me.

Jonathan May

Though not often a betting man, I am occasionally cajoled into such an enterprise, often to prove some kind of point or to hold something really lame at stake. In this case, it was a bet I actually won. The year: 1993. The place: Bulawayo Baptist Church, Bulawayo, Zimbabwe. I was bet by one of the sixth graders that I couldn’t eat a lemon, peel and all. At stake was $5, a terrific sum. Ice cream danced in my eyes. So I ate the whole damn thing, there, in the fellowship hall in front of twenty or so kids. It was easily the worst decision I’ve ever made. I gained $5 that day, and later ice cream, but I gave up my third-grade dignity then. I didn’t know what a metaphor was then, but I sure do now. A lemon is a lemon is a lemon.

Andrew Findlay

I went to a Tunica casino with a wallet filled with one hundred dollars. I left that Tunica casino with a wallet.

Mike Hannemann

I’m not a betting man – never have been. I went to Las Vegas once, for a bachelor party. It was pretty standard fare, one night was spent just gambling. We all found our own game and many of us went our separate ways. I found myself at the blackjack table. After $200 lost, I had to quit. I had hit my allotted budget for gambling. Before I could leave, an older man next to me handed me a $20 chip and said he’d teach me how to play. Two hours and a ton of luck later, I was up $400. I was ecstatic. I wisely decided to leave at that point, paid the guy back with an equal chip and strode back to the hotel room. The final table I passed was Casino War. $20 a hand. I paused for only a moment. Less than 30 minutes later, I had lost all $400 and was ready to murder someone.

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