The Biggest Sports Bets Of All Time

Whether you’re interested in having a punt on the NFL, NBA, or the MLB, there are opportunities all year round to put your money where your mouth is.

And no matter the level of your confidence, there’s no denying the overwhelming sense of excitement that comes with placing a bet.

Fortunately (or unfortunately depending on how you look at it), we’ll never experience the intense anxiety that comes with placing a multi-million dollar bet like these big-time sports bettors below.

Today, we’ll take a look at three of the biggest sports bets of all time.

“Sir Let It Ride” wagers $8 million on the Dodgers during the 2017 World Series

One sports bettor had Las Vegas bookmakers cowering after he had managed an impressive five-for-five betting record on the first five games of the 2017 World Series.

This bettor wasn’t just winning his bets; he was continually reinvesting his winnings into the next game.

So, after successfully tipping the first five games of the World Series, the man who would later become known as “Sir Let It Ride” had tallied up an impressive $8 million.

It was then – and only then – when the story of this relatively unknown Las Vegas handicapper would become public knowledge.

With his perfect record intact, and now people worldwide anticipating his next move, “Sir Let It Ride” let all of his winnings ride one more time by wagering all $8 million on the Dodgers to win Game 6 of the World Series.

By this stage, the Las Vegas sportsbooks were altering their lines before he could even make it to the counter to place a bet.

And to get his money down on the game, he needed to spread his bets out all over Las Vegas as no sportsbook was willing to take that much exposure (unsurprisingly).

Fortunately for this bettor, this story ends well.

The Dodgers won Game 6 and “Sir Let It Ride” walked away with $6 million profit from that game alone, netting an astounding $14 million total throughout six games.

If you’re wondering why he walked away at that stage and didn’t let it ride once more on Game 7…

Would you?

Billy Walters’ $3.5M bet on the New Orleans Saints at Super Bowl XLIV

Let’s take a trip down memory lane and reminisce about the success of Billy Walters, one of the most successful, controversial, and feared sports bettors of all time.

Walters was a highly-skilled professional gambler renowned for placing massive bets on American sports.

And because he was not just placing big bets, but doing so with great success, bookmakers in Vegas would not accept his wagers.

That wouldn’t stop Walters, however.

The lifelong gambler navigated around this problem by establishing an unbelievably comprehensive network that enabled him to make phone calls to “runners” who were situated in or near the major bookmakers in Las Vegas. These people – who were unknown to the bookmakers and each other – were the ones placing the bets, but it was always Walters making the call.

On an average Sunday, Walters was known to wager upward of $2 million on NFL games. Walters would typically risk between $50,000 and $250,000 per game, placing bets wherever he discovered a considerable edge.

But it was in February 2010 when Walters got a little too far ahead of himself and wagered $3.5 million on the New Orleans Saints at Super Bowl XLIV.

“All the stars were in alignment,” Walters explained in an interview with 60 Minutes

“Every bit of information that I had supported New Orleans. As a matter of fact, the combined consensus of the information that I had, we thought New Orleans was the favorite. We had New Orleans as a one-point favorite in the game.”

“I got caught up in the moment, and I started betting. Because the limits are so large on the Super Bowl, I actually bet more money than I intended to bet.”

Take a moment and let that sink in.

Billy Walters had an extra $3.5 million laying around that he could pick up and wager on the Super Bowl.

And if you recall how this Super Bowl ended, you’ll remember that the New Orleans Saints defeated the Indianapolis Colts 31-17 and Walters walked away with double his money.

Not bad for one day’s work.

“Sir Let It Ride” places a $3 million wager on the Philadelphia Eagles at Super Bowl LII

A sports bettor made headlines two weeks before the New England Patriots and Philadelphia Eagles were set to clash at Super Bowl LII in 2018.

This individual had just placed a $3 million bet on the Eagles at +5.5

Incredibly, it turned out to be the same famous sports bettor who profited $14 million after letting all of his winnings ride during the 2017 World Series.

So, when this sports bettor dropped a $3 million bet on the Eagles, it had the bookmakers in Las Vegas panicking.

It didn’t take long for the Patriots line to drop from -5.5 down to -4.5, skipping -5 entirely.

It’s certainly an act of bravery to bet $3 million on any sporting event, but it’s exceptionally courageous to wager money against Tom Brady and the New England Patriots.

But, of course, “Sir Let It Ride” had done it again.

The Philadelphia Eagles snagged their first-ever Super Bowl win and defeated the New England Patriots 41-33.

Arguably the craziest part of the “Sir Let It Ride” story is that he was a relatively unknown sports bettor, even to the major bookmakers in Las Vegas. Unlike many of the big-time players who wager millions of dollars at a time, “Sir Let It Ride” had only ever recorded a handful of UFC bets at the sports books in Las Vegas.

He won all of them.