For many sports fans, having a few bucks on the line for a fantasy football league or filling out a bracket for March Madness makes watching the actual games that much more fun. Dropping some cash at the blackjack or jumping in a poker tournament can be pretty thrilling and offers the chance to bring home some real winnings – if you play your cards right.
The Biggest Bets Aren’t What You Think
But some bettors go well beyond the bounds of what most would consider normal. These gamblers put some truly massive money on the line in the hunt for winnings. While you may put down a couple of hundred bucks on the Super Bowl, these bettors may wager what many might dream of eventually seeing in their retirement portfolio.
Here’s a quick look at some of the biggest bettors in history and what made them want to put it all on the line.
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Mattress Mack’s Million-Dollar Bets
The legalization of sports wagering has spread rapidly since the Supreme Court overturned the virtual ban on betting outside the state of Nevada in 2018. A total of 39 states, Washington D.C., and the territory of Puerto Rico have legalized some form of sports betting since then.
Betting on a game or booking that parlay has never been easier, and some handicappers can simply whip out a mobile phone in many states to make a bet. The industry has seen some truly eye-popping wagers in that time, but “Mattress Mack” McIngvale takes the cake.
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The businessman is the owner of the Gallery Furniture stores in the Houston area and has been known to shell out millions of dollars in bets through the years. That usually involves some kind of promotion for the stores.
For example, in 2023, he wagered $7.9 million on the Astros to beat the Texas Rangers in the American League Championship. The Rangers ended up winning in Game 7, and McIngvale was out a big seven-figure sum.
Big Betting is Serious Business
The businessman owner also had several wagers on the Astros to win the World Series that year, which would have paid him almost $51 million. He took the losses well, however.
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“Sometimes you get rained out, and you don’t look back,” McIngvale said at the time.
The Astros’ scores didn’t happen that year, but Mack has also had some huge wins through the years as well. McIngvale usually hedges his wagers with some major furniture promotions – giving some extra weight and media attention to his herculean handicapping. Customers who grab a new mattress have a chance to recoup their cash if the bets are winners.
The extra purchases as part of the promotion help offset the cost. The Astros came through the previous two seasons and delivered Mattress McIngvale a record return of $75 million over those years. That certainly will buy a lot of furniture and mattresses.
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Battling the Banker
Poker is a bit different than most games in the casino. Rather than battling the casino, players compete against each other and don’t have to face a house edge. The game takes plenty of skill with some luck mixed in as well. But the best players seem to rise to the top.
It’s also a game where amateurs can beat the pros on occasion, and one poker-playing banker put some of the game’s best to the test from 2001 to 06 in Las Vegas. Dallas-based billionaire businessman and banker Andy Beal challenged a group of poker pros known as “The Corporation” in heads-up Limit Hold ’em matches at some of the highest stakes imaginable.
Some of those involved in battling the banker included legends like Doyle Brunson, Chip Reese, Howard Lederer, Jennifer Harman, Phil Ivey, and others. While your home games may consist of some pots of 20 bucks or more, these stakes climbed as high as $200,00, meaning some massive pots were on the line with each deal of the cards.
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Each side went up and down for millions of dollars, and at one point, Beal recorded a $13.6 million win over four days in 2006. Some reports say Beal eventually lost about $50 million, but the banker has disputed that amount while admitting to losses.
The entire story was the basis for the book The Professor, the Banker, and the Suicide King by Michael Craig. Could more nosebleed stakes be in the future for the poker-playing billionaire? Craig notes in the book: “Several of the players remain convinced that they will see Any Beal again across the poker table.”
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Blackjack Bonanza
Blackjack is one of the best games in the casino for gamblers. When using basic strategy and choosing games with favorable rules, the house edge can be thinned to as low as 2% or less – certainly better than slot machines, which can come with an edge as high as 20%.
Australian business and media tycoon Kerry Packer was apparently a fan of the game and was known to be big, big, really big. Packer reportedly once won $20 million at the Aladdin Casino’s tables in London playing for as much as $250,000 per hand.
Professional golfer John Daly has been known to do some gambling himself and told quite a story about Packer on the Full Send Podcast. He said he witnessed the businessman close down the Desert Inn in Las Vegas after winning $52 million.
After losing more than $8 million the night before, according to Daly, the casino asked that he pay the sum in cash. Packer did the same, and the casino didn’t have the funds to pay out players.
“He always had boys who had cash on them in briefcases,” Daly said. “Kerry says, ‘Oh, let me write you a check. I’m going to gamble again tomorrow.”
The woman at the cage said the casino preferred cash, according to Daly. Packer’s briefcase guys ponied up the cash, and Packer was back at the tables the next day.
“To make a long story short, he hit them for $52 million the next day,” Daly says. “They had to borrow money to pay him.”
Packer died in 2005 and is remembered as one of the biggest gamblers in history.
Wheel of Fortune
Why not bet everything I own? That’s not a thought most would have, but that’s exactly what Ashley Revell dreamed up in 2004. After kicking back a few beers with friends, the 32-year-old Englishman decided to do just that.
Revell sold his Rolex, a BMW, golf clubs, and everything else he owned. He hoped to double up via a single spin on the roulette wheel. He then headed to The Plaza in downtown Las Vegas to wager $135,000.
The wager brought plenty of media attention, and Sky TV even filmed the events for a documentary. On April 11, 2004, he bet it all on red, which pays even money and gave him a 47.37% chance of winning.
“The night before I slept like an absolute baby,” Revell told the Telegraph in 2013. “There were no concerns whatsoever. Thinking back, it seems wild, but I was so convinced I was going to win. I was going down there to collect my winnings.”
Revell did just that as the little white ball landed on red 7. He walked away with $270,000 and quite a unique gambling experience.
“It was just a crazy time of complete happiness,” he said. “The whole experience taught me that what is important in life isn’t Rolexes or flashy cars, but sentimental things.”
