R. Paul Wilson On: When The Best Hustler Of All Time’s Scam Backfired

R. Paul Wilson On: When The Best Hustler Of All Time’s Scam Backfired

Con games, scams and carefully prepared proposition bets don’t always go to plan.

For legendary hustler Titanic Thompson, one of his most memorable propositions ended in a way that no one could have expected, least of all Thompson himself.

The collapse of Titanic’s scheme stunned his fellow gamblers and quickly became gambling legend.

The Set Up: Finding The Perfect Fish

Traveling by train with “Big Tony”, a former mob enforcer (also known as “muscle”) who was now a successful restaurant owner and occasional gambler, Thompson hit upon an idea that could potentially make him a lot of money the next time a big game went down near Tony’s restaurant.

Tony loved nothing more than a good bet, but he was well known as something of a dummy with very few brain cells to rub together when deciding how to bet.

At the card table, players would take a break, order a sandwich and get a drink whenever Tony had a difficult decision to make.

But while Tony was well known for being something of a dummy, he was equally notorious for his past deeds on behalf of some very bad men who Tony still called “friends”.

As a result, while Tony was certainly no genius, no one would dare say as much to his face.

Sharing a train carriage with Tony, Titanic Thompson hit upon an idea where Tony’s reputation might be used to set up an unbeatable bet.

Thompson already had a fistful of scams devised for railway journeys like this. 

For example, it was well-known in the gambling community that Ti would pay people to dig up signs alongside railroad tracks and move them 10 or 20 miles closer to a destination.

Later, he could make bets about when a train would arrive and suckers who spotted the re-positioned signs would make their guess based on information that was now extremely unreliable!

Tony, however, was well aware of Ti’s tricks so going after his bankroll would be tricky at best and dangerous at worst.

So Thompson took an entirely different approach:

“Doesn’t it bother, you Tony?” he asked.

“What?” Tony replied.

“That everyone thinks you’re so damned stupid.”

A chill fell upon the carriage.

Tony’s mood darkened, a hint of the man he used to be.

“A little respect, please Mr. Thompson. I wouldn’t want to upset me, if I were you,” Tony warned.

“Don’t misunderstand me, Tony, I don’t mean to be rude but it upsets me that a man like yourself, who has made a successful business with his savings and who plays a mean hand of poker — it upsets me that people think you’re not even smart enough to spell your own name.”

Tony was confused, uncertain whether Thompson was making fun of him or applauding his success.

Finally, he decided it was the latter, thanked Ti for the compliment and returned to watching the world pass by their window.

“In fact, I’d like to prove them wrong. How about a little bet?”

Here it comes, thought Tony.

But, like all of Titanic Thompson’s victims, he couldn’t resist hearing what the hustler had in mind.

“Let’s say I write down two 10-letter words and you memorise how to spell those words during our little journey. And at the end of the trip, when the conductor comes to collect the carriage fees for our drinks and food and such— if you can spell both words, I’ll cover the bill. What do you say?”

Tony was intrigued.

The price of the carriage fees was nothing to him and he would often pay them himself anyway, even if he was traveling with several people. So what the hell was the catch?

How could he say no? It was worth paying the bet to find out.

So Titanic Thompson wrote down two 10-letter words: ANTHROPOID and RHINOCEROS.

Tony memorised how to spell the words, reciting the letters for hours and at the end of the journey, accurately spelled both words.

As promised, Thompson paid the conductor, covered Tony’s lunch and bid him farewell.

But the scam had only just begun.

Titanic Thompson
Titanic Thompson – one of the most notorious hustlers in history. [Image: Pinterest]

The Proposition: Too Good To Refuse

For the next couple of weeks, Titanic Thompson dropped into Tony’s restaurant, bought a coffee and slid a 10-dollar bill across the counter, challenging Tony to recall both ten-letter words.

Just as he’d done at the end of the train journey, Tony recited each word, letter-by-letter like a kid singing their ABCs. Once Thompson was certain Tony had both words “down pat” he set up a big poker game nearby.

After several hours, the game paused for a break and the players followed Titanic to Tony’s restaurant where the big man was hard at work on a crowded weekend night.

After dinner, while the gamblers told stories, laughed and relaxed, one of them noticed Titanic watching Tony as he chatted to customers.

When asked what was so fascinating, Ti gave them all the hook:

“It’s amazing to me that people dismiss Tony as some sort of dummy. I’m here to tell you, that man’s a lot smarter than people think.”

After a pause to process what Ti had said, the table erupted into laughter.

“I’m serious, he’s a successful businessman, he can play a decent hand of cards and believe it or not— he loves the New York Times crossword puzzle.”

Of course, no one believed a word of this and that played right into Titanic Thompson’s hands.

“Okay,” he said. “Tell you what, I’ll write down five 10-letter words, you can pick one and I bet you a thousand bucks – each – he can spell that word perfectly.”

Now they were interested but Titanic Thompson’s reputation was Titanic Thompson’s reputation, so no one was going to let Ti decide what words they could choose from.

Naturally, Ti had a solution – which he had set up days earlier.

Calling over the waitress, he offered her 20 bucks to write any five 10-letter words on a napkin, which she duly did, as Ti had previously (secretly) instructed her.

Now the table had five “random” words to choose from:


As Titanic predicted, the gamblers quickly dismissed “RESTAURANT” since it was written on the window. “CANNELLONI” and FETTUCCINI” were no good because they were Italian words and Tony might have an advantage given his heritage, so the group decided that “RHINOCEROS” would be the perfect choice.

The Sting: When It All Goes T*ts Up

With the trap set, everyone waited for Tony to stop by their table and Titanic was ready with a 10-dollar bill in his hand to challenge Tony’s now well-practiced spelling ability.

So after a few pleasantries, Ti flashed the palmed 10-spot and said “Tony, can you spell RHINOCEROS”?

“I sure can!” he said, and spelled the letters A-N-T-H-R-O-P-O-I-D.

A sudden silence fell upon the table, the gamblers shocked that Tony accurately spelled the other word that he wasn’t even asked to spell!

At the same time, it dawned on Ti that while he had made certain Tony could spell both words, he had neglected to make sure Tony knew which spelling was for which word!

After a few seconds, everyone realised it was a set-up and how it had gone wrong.

Pretty soon, the gamblers were laughing so hard, they could barely breathe.

Tony, of course, was pleased with himself so Thompson handed over the 10-dollar bill before reaching for a thick roll of hundreds to settle the enormous bet he’d just lost.

An anthropoid in the wild. [Image: Unsplash/JoelHerzog]

The Lesson

As I’ve learned filming The Real Hustle, playing against casinos and making a few moves at the poker table, a seemingly perfect set-up can sometimes fall apart in the most spectacular and unexpected ways.

Next time you think you can’t lose, remember that even history’s greatest hustler got caught out from time to time.