I Lost 25 Blackjack Hands In A Row, And Anthony Curtis Says It’s OK

It defied description, and still does, as variance reared its ugly head
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I lost 25 hands in a row playing online blackjack on DraftKings.

It happened over the course of two sessions, and the vast majority of the losses were via free credits, so I only lost $5 on the deal. But again: I lost 25 consecutive hands of blackjack. (See the screenshots below.)

25 in a row

If I were Martingale-ing this, starting with a dollar on hand number one, by the time I had to pony up for the 26th hand — which I pushed before losing three more hands — it would’ve meant a bet of $16,777,216.

Not sure I would’ve gotten the marker for that one.

If blackjack were a 50/50 proposition — which it ain’t — the probability of this happening would be .0000000298. That means it’s a .00000298% chance. If my math skills are correct, that means I can expect to lose 25 hands in a row roughly once every 33 million times.

In short: This should never happen. Ever. To anyone. But it happened to me. I lost 25 hands in a row playing blackjack. 

It caused a bit of an existential crisis. I mean, what purpose is there in life if it’s possible to lose 25 hands in a row? How can one man continue?

And while I recognize “existential crisis” may be a bit strong, I’m not really sure I’m kidding. This may be the most gobsmacking experience of my life. It’s so twisted. The math is inconceivable.

It would’ve been a lot better if I won 25 times in a row, I’ll tell you that.

A Hall-of-Famer weighs in

“It’s an extremely rare event,” Anthony Curtis told me. “With blackjack, you’re going to lose 52.5% of the time. So .525 to the 25th, that’s a big number.”

Curtis should know. The author, publisher, gambler, and recently enshrined Blackjack Hall of Fame member went out to Las Vegas in 1979 after dropping out of Duke to pursue his gambling dreams.

And after his first 48 hours, he was living a nightmare.

“One of the best things that ever happened to me is when I came to town, I was studying blackjack like crazy, I was 21 with $2,800 on me,” Curtis, who has been publishing the Las Vegas Advisor since 1983, told me. “The first day I won $29, the second day I lost $1,800. I just had no inkling that could possibly happen. I had to go right to work, had to get a job. And that recollection stayed with me forever. I’m always aware, always had an understanding of risk because of what happened to me. But I didn’t understand it coming in. And when it happened, I thought it was damn near impossible. But when I looked at it later, I was like, this was very much within the realm of probability and possibility. This was not a rare event.”

Curtis says big losses – or losing 25 times in a row (!) – are important milestones in the career arc of a professional gambler.

“I think some people are born with [the ability to mentally withstand a big loss], but there are very few,” he said. “I think you have to experience it. I’ve seen the ruination of a lot of players who didn’t experience a big loss early. I knew a guy who won $30,000 playing Keno when he first came to town. Now, Keno is a terrible game. He’s playing electronic Keno, maybe a 10-11% disadvantage, but he won $30,000, and blew it all back plus the same amount twice over. He lost another $30,000 thinking it was going to happen again. I’ve seen a lot of players start off really well and don’t have a sense of how bad things can go, and then they don’t know how to handle it.”

Pride cometh before the bust

Well, I’m not now, nor am I ever, planning on being a professional gambler. My wife won’t let me, mostly, but I also know – if I’m being perfectly honest with myself – that I don’t have the mental game for it. My heart starts skipping beats when I have more than $25 floating around on a bet. The professional gambler’s life is just not for me. Especially the losing part.

“In terms of the mindset of it, it’s something that gamblers have to get used to, that this sort of thing can happen,” Curtis said.

Well, I’m used to it, all of a sudden. Just about the saddest gambling story you’ll ever hear. I mean, 25 in a row. It numbs a man.

“I’ll tell you what, I don’t know anybody who’s lost 25 hands in a row,” Curtis said near the end of our call.

This stopped me in my tracks for a moment. Here’s a guy who’s been a pro gambler for over 40 years, his whole adult life in Vegas, probably one of the more plugged-in guys out there. If someone lost 25 in a row, Curtis would hear about it, right?

“I knew a guy who lost 21 football bets in a row. That’s a coin flip, he’s betting the lines, and lost 21 straight,” Curtis said. “That was the worst I ever heard of until right about now. I don’t think anyone is going to take that one away from you for quite some time.”

So, according to Anthony Curtis, one of the most well-known, respected, biggest gamblers of all time, I may be the unofficial — actually, screw that, I am the official world record holder for most consecutive losses playing blackjack. I think I’m legitimately going to contact the Hall of Fame, which is located in the Barona Casino in San Diego. I deserve a plaque.

Look ma! I made it!

Photo: Shutterstock

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