Billy Walters: Biggest Bets, Wins and Losses

Billy Walters

From TheRealBillyWalters Website

A true rags to riches story, William T. Walters was raised by his grandmother in a house with no running water or indoor plumbing.

This poor start would prove to be the making of Billy who learned to be entrepreneurial early on, and developed a strong philanthropic streak due to his early life in poverty.

From age 7 he was cutting lawns and running a paper route, progressing to work in a bakery and a gas station in his teens. It was in automobile sales that he first made real money though, in the 1960s. Taking a proactive approach, he would work 80 hour weeks earning the equivalent of £400k per year by cold calling customers to get cars shifted, and eventually ended up with his own business.

Throughout all of this time, he was betting. In fact, he lost his very first bet, made when he was just 9 years old, using money from his paper route.

It wasn’t until 1982 that Billy Walters started to show real promise as a sports bettor, although he had already made and lost millions in the casinos and at the poker tables. He got involved in analysing sports outcomes using computers and lots of data, positioning himself perfectly for the technological advances that were to come.

He got to the point where he was betting so much that he could move the market any way he wanted it to go, although he had to do so using a small army of ‘runners’, because bookmakers had become all too aware of Billy Walters, and many feared him so much that they wouldn’t take the bets if they knew they were his.

Not surprising when you consider that in 30 years of sports betting, only once did he ever finish up poorer at the end of the year than he was at the start. He is thought to have made hundreds upon hundreds of millions of dollars, becoming something of a Robin Hood figure by using much of it for good causes.

Sadly for Billy, making millions from sports betting wasn’t enough. In 2017 he was found guilty of insider trading (using non-public information to buy/sell stocks at the most opportune times) and ended up with a 5 year jail sentence, eventually being released early in 2021. At this point he was well into his seventies, and he decided to publish an autobiography, which, considering he is known as the most dangerous gambler in the world, is probably be quite a read.

Billy Walters's Biggest Bets

$3.5 Million Winner for Billy Walters in Superbowl XLIV

Bet: $3,500,000 (£2,898,245) - New Orleans to Win the Superbowl - Won

Widely believed to be the biggest bet Billy Walters ever placed, his $3.5 million bet on the New Orleans Saints to beat the Indianapolis Colts was a bold one and no mistake.

It was a huge sum of money considering the Colts were the favourites with a 5.5 point lead, but many people thought this line was nuts, and betting volume around the Superbowl moves the line in funny ways. Who knows, maybe Billy moved it himself?

Regardless, at some point - and we don't know when - Walters got his money on, and will have profited hugely from his bet, even if he took very short odds.

$2.2 Million Winning Bet as Billy Walters Backs USC over Michigan

Bet: $2.2 Million (£1,100,000) - USC to Beat University of Michigan - Won

Since Billy Walters is one of the most secretive sports bettors there is, information on the bets he makes is extremely hard to come by, but this one for $2.2 million is on record and thought to be one of his biggest ever.

He backed the University of Southern California Trojans to beat the University of Michigan Wolverines in the Rose Bowl Game at the end of the 2006 NCAA Division 1 FBS football season, and beat them they did.

The game took place on January 1st 2007 too, so while the estimated $7.7 million he won already sounds pretty impressive, it would have been worth a heck of a lot more back then.