billy walters, world's biggest gamblers

Billy Walters might just go down in history as the most infamous name in high stakes gambling.

Walters grew up in a small town called Munfordville in Kentucky. His family didn’t have much: not even indoor plumbing. They were, however, avid gamblers. Walters’ father was a keen poker player and his uncle was actually a professional gambler for a time. These figures in childhood would have a profound effect on Billy Walters. His keen interest in the punt developed early.

At the age of nine, Walters took the money he earned on a paper round and wagered it on the World Series. That bet would be the beginning of one of the great gambling careers.

As he got a little older, Walters raised what money he could by selling second-hand cars, and at the same time set about becoming a bookmaker. This was, of course, illegal in his native Kentucky. He was prosecuted and fined $1,000.

Walters didn’t need any further incentive to move. He headed straight to the gambling mecca of America: Las Vegas

Billy Walters: Legendary Sports Bettor

Walters made his name as a sports bettor, but in the early days also played poker and other table games. He was somewhat successful in poker tournaments and won at roulette. The story regarding his roulette success goes that he gained an edge by identifying that older roulette wheels wore in different places, making them predictable and ultimately profitable.

In Vegas, Walters connected with two others to form one of the first computer-based betting syndicates. Walters, Michael Kent and Dr Ivan Mindlin exploited early data techniques to build computer algorithms for sports betting. Walters’ role was largely to get the money on, exploiting the weakest lines the group had identified placing the biggest wagers possible. The size of the bets skyrocketed and ultimately, so did the profits.

Operating in the pre-internet era, Walters and his associates were ahead of their time. One of their famous ploys was dispatching runners to the airport to grab interstate newspapers immediately, getting a jump on any sports news and using it to their advantage. Before long the runners were also placing bets on behalf of Walters, with sportsbooks unwilling to take him on.

Property Deals

As Walters’ wealth grew, so did his search for bigger edges – both in and beyond gambling.

Walters used his wealth to expand into property and the stock market. An avid golfer who plays off scratch, in 1996 he won a contract to develop a Las Vegas golf course. It was Walters’ idea to purchase the land outright, and he negotiated an extremely good price with the city to do so. Real estate values in Vegas would soon take off, with Walters and his partners gaining planning permission to redevelop the land into residential property. This would prove Walters’ biggest payday, pushing his personal wealth well beyond $100 million.

The stock market & coming undone

On top of decades of success in sports betting, Walters had long played the stock market successfully. But in 2017, Billy Walters’ luck ran out.

Walters was receiving stocks tips from Thomas Davis, chairman of Dean Foods. Davis reportedly had a gambling habit and fed tips to his friend Walters. Investigators would ultimately charge Walters with insider trading. He was convicted and sentenced to five years in prison. In 2020 Walters, 73, was permitted to serve the remainder of his sentence in his California home… where a cable television subscription and phone access will be welcome luxuries!

Insights from Billy Walters

Billy Walters may live a somewhat more low-key existence now, but the proof of Walters’ success is clear: hundreds of millions in profit over decades, and an empire that includes mansions, golf courses, hotels, property developments, car dealerships, a private jet and various other business interests.

So what are the lessons we can learn?

Information gives you an edge

Billy Walters surrounded himself with sharp minds of very different backgrounds whose only contact with the syndicate was a direct line to Billy. They didn’t know or have anything to do with each other. Walters employed an array of experts in the roles of consultants, statisticians, mathematicians and computer programmers to help him compile, analyse and ultimately profit from huge amounts of information.

Whether it’s business or gambling… value is everything

“If you value something at ten, then you’re a buyer at eight and a seller at 12.”

Walters wasn’t emotionally attached to teams or players. His concept of value is very different to how many punters operate, which is to back a favourite team or horse without seriously analysing whether the odds available represent good value.

The bigger the value, the bigger the bet

The Walters team produced their own lines and only bet when they are different to the market. The bigger the difference between their line and the market odds, the more they bet.

He had incredible confidence in his own numbers and looked to exploit his advantage the most when that edge is the biggest. That’s not to say that it’s all about making one big bet – Walters spreads out his bankroll across many opportunities where he has a positive expectation.

… but we’re not talking huge margins

Simply tossing a coin will get you a 50% strike-rate.

But to be profitable, betting at the standard odds of $1.90 requires a strike-rate of 52.4% or more.

For all of his work and success, Walters winning strike-rate is estimated to be ‘just’ 57%. But the sheer volume of his bets and the ability to optimise his bankroll management has enabled him to amass hundreds of millions in profits.

Don’t expect instant success

“I know what every sucker thinks, because I used to be one. I can assure you that every successful gambler I know has been through some monumental failures on his way to getting there.”

Walters went broke many times early on and described his younger self as a compulsive loser and gambling addict.

Early failures are a very common experience amongst gamblers who ultimately become very successful. Many punting lessons are learned the hard way.

Don’t become a dinosaur

“I probably had to re-invent myself 25 times in the last 20 years. If I hadn’t re-invented myself, I would have been out of business. That goes for anyone in any business. There’s going to be constant change of any industry you’re in and if you don’t change with it and you don’t change ahead of it, you become like a dinosaur. You become extinct.”

“The game of handicapping sports is really the same game as it was 40 or 50 years ago. It’s much more competitive now, and the numbers are much better than they were in the 80s, but it’s still the same game. It still comes down to evaluating information.”

The edge that came from reading all the small-town newspapers disappeared as soon as the internet became widely available. Edges disappear over time – sometimes gradually and other times quite quickly.

Walters repeatedly adapted his approach to stay ahead of the game, whilst understanding that the fundamentals of gambling success remain unchanged.

Execution is as important as edge

“The computer whiz kids who are involved in sports today don’t have a clue, I mean a clue about how to bet their money. They don’t have a feel at all for which way the line is going to move. There is a big difference in knowing how to bet and when to bet your money in sports. It is almost as important as handicapping.”

Don’t be in denial

“A lot of people have a difficult time stepping back and doing a re-valuation and deciding ‘I was wrong’. A lot of people want to continue on in denial until they’re completely broke.”

Long-term winners DO exist

Walters amazing ability to beat liquid markets over such a long period is living proof that success is possible.

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