Lessons from one of gambling’s greatest hustlers

Born at the tail end of the 19th century in the sleepy backwater of Missouri, Alvin ‘Titanic’ Thompson graduated from flipping pennies on his porch to becoming one of the greatest gambling hustlers of all time.

Thompson was an accomplished ambidextrous golfer - regarding playing on the PGA Tour as taking a pay cut - a skilled poker player and a master of dice and cards. He travelled the length and breadth of the US with a bag of clubs - left and right-handed - in the boot of his Piece Arrow, along with a bowling ball, horseshoes, a gun and a stack of cash looking for marks to hustle.

His targets were the rich and famous or anyone foolish enough to take him on at dice, pool, golf, poker, coin-flipping or accepting his exotic and outlandish propositions.

Different era, same game

Though Titanic Thompson is more than mere legend, many of the stories of his exploits have evolved over time to become modern-day myths, none more so than the apocryphal origin of his name. The word was that he was named Titanic because he managed to get off the famous sinking ship by dressing as a woman.

The maths, the semantic of the prop, the attention to detail and timing, the understanding of body language all put him way ahead of his time in accounting for behavioural weaknesses.

The truth is that Titanic earned his name from one of the proposition bets for which he became so infamous. Given their humour and ingenuity they provide a much more entertaining, yet no less relevant illustration of what it means to bet with an edge, a message that is like a mantra across Betting Resources.

In that sense Titanic was way ahead of his time. He had no formal education - in fact he was illiterate - but possessed an intrinsic appreciation of the how a gambling proposition worked and also realised that along with practice and research, knowing when the odds were in his favour were critical to gaining and holding an edge.

As his ambition grew he employed the service of a former Columbia University maths Professor, Patrick McAlley for a crash course in the mechanics of betting odds. He was especially interested in the probability of counter-intuitive bets in dice, poker and coin-flipping which he saw as rich pickings, especially for side bets.

Without knowing it, Alvin was scratching the surface of the field of behavioural psychology that the likes of Kahneman and Tversky would receive a Nobel prize for more than 50 years later.

Titanic - He sinks everybody

After a stint as a side-kick in a touring sharp shooting show, Thompson found himself in Joplin, Missouri in 1912 - around the time that the Titanic was about to (literally) go down in history - hustling in a pool hall called Snow Clarks for sums equivalent to the average annual salary of the time. According to Kevin Cook’s excellent biography, Titanic was on his way out when he noticed a sign saying “$200 to any man who jumps over my new pool table”.

Titanic Thompson understood that knowing when the odds were in his favour was critical to gaining and holding an edge.

To the average Joe shooting a few frames, the sign was rhetorical, but to Titanic it was a challenge to both his wit and his physical prowess; both of which were such exceptional attributes. His skill was in instantly recognising that a proposition, such as jumping a pool table, may on the face of it seem impossible, but when looked at from a different angle, it could be turned in his favour.

“I can do it” he bragged, to the derision of the locals. Even if he could somehow achieve the Herculean feat of jumping the table, Snow Clark and his regulars felt that the challenge was such that the injuries sustained wouldn’t justify the bounty - he simply didn’t expect to pay out. 

Thompson walked out, leaving the doubters to assume he had been humiliated, only to return 10 minutes later…... dragging a mattress he had bought from a nearby motel.

He jumped the table, with the mattress breaking his fall, earning him both $200 and a name that would stick with him for life. Titanic - because according to Snow Clark - “he sinks everybody.”

One of Titanic’s favourite and more bizarre hustles involved throwing a peanut, walnut or piece of fruit over a building.

Thompson didn’t drink or smoke, he simply lived to gamble, and though thrill was more important to him than the accumulation of wealth - he died with nothing but $400 stuffed in a sock - he was a dedicated student of every aspect of gambling. For aspiring gamblers, the lesson here is to enjoy the anecdotes, appreciate his unique skills, but don’t overlook his shortcomings.

The maths, the semantic of the prop, the attention to detail and timing, the understanding of body language all put him way ahead of his time in accounting for behavioural weaknesses.

20 Miles to Joplin

Alvin spent his time almost exclusively with other gamblers. He was adept at finding a prop in the mundane or ordinary - or at least making it appear that way. This art of deception and meticulous preparation played a key part of one of his most famous grifts.

Driving back to Joplin one afternoon from a fishing trip with a pair of poker players - Beanie Benson and Hickory McCullough - the trio passed a road crew planting a new road sign saying 20 miles to Joplin.

The next time the group went fishing Thompson plied them with drinks and on the return journey remarked that the sign was wrong and it was never 20 miles to town.

“Sure it is, they are careful about that sort of thing”, Beanie said.

“I’ll bet you $100 it is no more than 15 miles”, Thompson retorted.

“I’ll bet you $500 you are wrong”, Beanie shot back - $500 was more than a month’s decent salary.

“I’ll take 500 of that”, Hickory chimed in.

“Boys you got a bet”, and the bet was on. 

The trio were glued to the car’s odometer in silence as they drove back to town, which showed the journey was no more than 15 miles. Cursing the Roads Department, the pair paid up and swore to never bet with Titanic again.

Of course what Benson and McCullough didn’t know was when Titanic had first seen the sign being planted, he paid someone to drive him back from Joplin to enable him to dig it up and move it five miles closer to town. The anecdote beautifully captures Thompson’s talent for setting a prop - his motivation was money, his ingenuity and bankroll provided the means, he just had to wait for the opportunity to present itself. And over the next 50 years, there were plenty of opportunities; here are a selection:

The checkers set-up

Hearing of a $10,000 challenge put out by a Checker’s Champion, Lock Renfro, in Kansas for anyone who dared to take him on, Titanic accepted despite his experience of the game going only as far as his school days. Sat opposite the Champion, Titanic was nervous and ponderous but gained the upper hand, dragging the game out as if for sport. Renfro wasn’t to know that through a peep-hole in the ceiling US Chess Champion, Harry Lieberman, was relaying advice to Titanic via a thumper which was attached to his leg.

The lucky horseshoe

Horseshoe throwing was a big part of rural culture in 19th and early 20th century. Thompson heard that a pitcher named Frank Jackson had an open challenge to all-comers for any amount. Thompson had no especial background in the sport, though the underarm motion had similarities to bowling, but drove to Des Moines, Iowa, and set up a court in an alley outside his hotel and set about practising. 

If you don't get this elementary, but mildly unnatural, mathematics of elementary probability into your repertoire, then you go through a long life like a one-legged man in an ass-kicking contest. Charlie Munger

After deliberating pitching some duff throws Titanic convinced Jackson to put down $10,000. While Titanic ringed every pitch the Champ was about a foot off, and begrudgingly paid out. Little was he to know that the stake on Titanic’s court - where he has spent so many hours practising - was at 41 feet, instead of the regulation 40 feet.

Tossing a peanut over a building

One of Titanic’s favourite and more bizarre hustles involved throwing a peanut, walnut or piece of fruit over a building. Marks were understandably sceptical and took his challenge, including Al Capone. Most of the time Thompson paid a fruit seller to hand him a loaded item - with lead in it - giving him enough weight to make the challenge. Capone being wary insisted on crushing the lemon - the variant for this version - so it was left to Titanic’s slight of hand to palm a replacement and pull it off.

Sometimes these props came down to the wording. ‘I bet I can get a watermelon on top of that building’ would be achieved by simply taking a lift and the fire escape with fruit under his arm.

Going toe-to-toe with a heavyweight

While in residence at a hotel in the exotically named town of French Lick, and a during a break in a poker spree, he met a big-headed prizefighter whose ego made him a perfect mark. He bet the boxer $1,000 he couldn’t knock him out with them both standing on the same newspaper. This seemed easy money - as it always did - until Thompson laid the Spring Valley Herald across the threshold of a door, so he stood toe-to-toe with the boxer, then stood off the paper to shut it and resume his position. Easy money indeed.

The search for an edge remains the same

When Titanic was born there were just 10 miles of paved roads in the entire USA. By the time his career was on the wane in the 1970s he was being recognised in Vegas which effectively took away most of his edge. As gambling has evolved into a common recreation, layers have become more sophisticated. Yet the search for an edge remains the same, it is just that the methods have changed.

Titanic Thompson would probably have had a lot of time for Romanian mathematician, Stefan Mandrel, who in the 1970s bought every ticket combination in rollover lotteries where the jackpot presented the unique situation of a positive Expected Value against his outlay. He retired a millionaire, living on a Pacific Island.

Titanic Thompson's motivation was money, his ingenuity and bankroll provided the means, he just had to wait for the opportunity to present itself.

The hole in 1 gang provides another colourful example of finding an edge, this time from the 1990s in the UK - see this article on intuition for more. A group of astute gamblers exploited independent bookmakers’ poor grasp of the underlying chance of a hole-in-one at televised golf events. They dished out ludicrous odds far in excess of the true underlying probability and were duly punished.

Our interview with a famous sports bettor, Lewis Deyong, shone a lot of light on what was a golden era for finding value, if you knew where to look, but ended with the acceptance that times and methods have changed. However, there are still opportunities for bettors to make a profit - if profit is your aim - that don’t involve digging up road signs but require as much conviction and dedication and above all, an understanding of when the odds are in your favour. The best way to communicate the required mindset might be to end with a quote from a famous investor, Charlie Munger, Warren Buffet’s right-hand man.

"If you don't get this elementary, but mildly unnatural, mathematics of elementary probability into your repertoire, then you go through a long life like a one-legged man in an ass-kicking contest.”

Titanic knew this, and was always looking for one-legged men. Keep two feet on the ground by either understanding how betting works or simply see it as recreation.