Biggest Losing Bets

losing betAnyone who has engaged in sports betting or casino gaming before will have the same mindset – the idea is to win. Of course, this is pretty much a given. Ideally though, you should be entering into these gambling opportunities with the thought process that you may potentially lose as well. Otherwise, you’re more than likely setting yourself up for an unexpected fall – and that’s never a good way to go about betting.

Not everybody can get the hang of this though, and it has led to some extreme losses over the years because of this. Some people go in with the intent of placing huge bets because, of course, if they’re winning bets, they pay out large sums. However, in the case of losing, they see you stripped of lots of money, and that’s never a good feeling to experience.  Here we aim to take you through a glimpse into some of the biggest losing casino and sportsbook bets in history. Maybe you can learn something from these people placing such severe bets and suffering devastating losses.

William Lee Bergstrom ($1 million)

pass line crapsKnown as The Suitcase Man or the Phantom Gambler, William Lee Bergstrom was born in Austin, Texas in 1951. Prior to involving himself in gambling, Bergstrom made a living by selling real estate and owning property within his home state. However, in 1980, he made quite the impact on the gambling world.

It was in September of 1980 that he arrived at the Binion’s Horseshoe Casino (now going by the name of Binion’s Gambling Hall & Hotel) in Las Vegas, Nevada. With him, he had two suitcases. One of these contained $777,000 in cash and the other one was completely empty. It was common practice at the time for owner of the casino Benny Binion, to accept and honour a bet of any size from a player’s first time visiting and playing there.

Bergstrom chose to remain anonymous at the time, but he proceeded forward with betting the entire $777,000 on a single bet of a dice, which he went on to win. This saw him profit by exactly the same amount as he had wagered, with the winnings being stuffed into his empty suitcase. He then left and pretty much disappeared for three-and-a-half years. After making his return to the casino, he placed several other winning bets in March of 1984 and then returned again in November of the same year.

This time, he placed a bet of $1,000,000 coming from $550,000 in cash, $140,000 in gold Krugerrands and $310,000 in cashier’s checks. He placed the same Don’t Pass bet on the same game as he had when he made his original huge wager there. However, this turned out to be a failing bet and Bergstrom lost his $1 million bet. According to some reports, Bergstrom never got over this monumental loss and proceeded to commit suicide on February 4, 1985.

$19 Million Lost Through Baccarat

baccarat wordCasino dealers must have witnessed a lot within the establishments that they work in, but the biggest loss one of them saw was $19 million during a session of baccarat. A Malaysian player joined a game in a private room of a hotel and casino, and supposedly arrived at the table still in his pyjamas!

The player placed several large bets on the game, starting with a $500,000 wager and then a $600,000 wager. While the dealer noted that the player did win a $300,000 bet later on, he supposedly became furious that his sole win was the smallest one he’d placed and none of the big ones. This resulted in the dealer being changed at the customer’s request, although the player still went on to lose a total of $9 million on that day.

According to the source of this story, he remained at the hotel for one week and proceeded to lose $10 million the following day on baccarat again. That’s quite the hefty load to lose out on during baccarat gameplay, and not one that most people have the ability to simply throw away.

Charles Barkley ($10 million)

It’s not only the average everyday person who gets involved in gambling and loses, but sports stars are also capable of getting out of control. One such case is that of Charles Barkley – an 11-time NBA All-Star and the 1993 MVP. Unfortunately, the basketball player is pretty much synonymous with having a gambling problem as well as his NBA career. During his 16-year career playing for the top basketball league in the world, Barkley is said to have lost the entirety of his fortune.

Barkley himself did not consider his gambling habits a problem, though. During an interview conducted by ESPN, he out-rightly admitted to losing about $10 million through participating in gambling, further commenting that $2.5 million of it had been lost during a single 6-hour session of blackjack. Of course, sportsmen make so much money, that it probably doesn’t stand out as being that much of a problem in the first instance.

Yet, in 2008, Barkley was at the centre of quite the scandal when the Wynn Las Vegas casino filed a serious complaint against him. According to the establishment, the basketball star had not paid of his gambling debt of $400,000. He managed to pay the debt off in the end and stated that he would stay away from gambling for the foreseeable future. Speaking of his gambling habits in 2015, he said that he had lost around $20 million through betting in Las Vegas over the years.

Michael Vick (Everything)

Despite being a former professional American football quarterback, Michael Vick has had quite the troubling life. Primarily operating as part of the Atlanta Falcons and the Philadelphia Eagles, Vick played through 13 seasons in the NFL, being the first overall pick of the Falcons in the 2001 Draft.

Yet, his career came to quite the grinding halt in 2007 when he pleaded guilty towards being involved in a dog fighting ring. This led to him spending 21 months in federal prison and just before he was released, he was dropped by the Falcons. Vick signed with the Eagles in 2009 and remained as a player for the team for five years.

However, he actually lost his entire fortune due to illegal gambling activities. The financing and organisation of the previously mentioned dog fighting ring took him around 10 years to clear up, and it was due to this that the Falcons also took him to court. They demanded that he payed back a huge chunk of his signing bonus; something which the court ruled in their favour on and saw Vick stripped of around £14 million.

He filed for bankruptcy while still in prison, stating that he owed between $10 million and $50 million in debts. A total of 99.9% of his debts were paid off by November of 2017, according to a report by ESPN. While he may be back on the straight and narrow now, operating as a studio analyst for Fox Sports, the likelihood is that nobody (especially Vick himself) will forget his trials and tribulations around the world of illegal gambling.

Harry Kakavas ($20.5 million)

problem gamblerYou’re certain to become infamous in the gambling world when you wager almost £1 billion on casino games over the course of 15 months. Naturally, he didn’t lose all of those bets, but he did suffer losses of approximately £11 million in total, which is an extreme amount in itself for casino gaming.

Having been a problem gambler for many years, Harry Kakavas ended up being sent to prison in 1998 for defrauding a large Australian corporation of more than £160,000. That money was then used to fund his gambling habits. Yet, suffering from serious losses, Kakavas proceeded with self-excluding from the Crown Casino located in Melbourne.

Yet, it was six years later that he found himself being drawn back to the very same establishment, and it was there that he lost a fortune. Kakavas ended up taking the Crown Casino to court, claiming that it had taken unfair advantage of him when they knew he suffered from gambling addiction. The court heard that Kakavas had a total gambling turnover of $1.5 billion and losses equating to $20.5 million. In his defence, Kakavas stated that the casino had lured him back there with exceptional incentives and the possibility of using the casino’s own private jet.

The final ruling given in 2013 though, was that there isn’t a general duty upon a casino to protect gamblers from themselves – which may well have been the case at the time. Therefore, Kakavas didn’t get any of his losses back from the Crown Casino and is now back selling real estate according to sources.

Michael Jordan ($1.2 million)

michael jordanObviously, Michael Jordan is synonymous with basketball, but perhaps you didn’t know about his betting antics as well. As it happens, he’s quite the notorious gambler and it is said that his early retirement from basketball came as part of a secret suspension due to his habits in this field. One of Jordan’s friends Richard Esquinas wrote a book about an incident where the basketball star lost $1.2 million to a businessman.

This bet was made as part of a 10-day golf and betting binge, and while Jordan managed to regain some of his funds through play, he only managed to negotiate it down to $300,000. Of course, this is of little surprise when you understand that Jordan has been known for playing a single hole of golf for $100,000. Therefore, the fact that he ended up racking up a $1.2 million debt during the course of that 10-day binge is of little awe. For many people though, that would be quite the monumental loss. Perhaps for one of basketball’s biggest stars, $1.2 million is closer to pocket money?

Wayne Rooney (£500,000)

wayne rooneyWayne Rooney is known as one of the UK’s biggest football stars, having played for teams like Manchester United and Everton. However, he’s also infamous in the gambling world as well. In 2017 though, he went a bit overboard with his betting habits, arriving at the 235 Casino in Manchester at midnight one day and alleviating himself of £500,000 in a two-hour gaming session.

Rooney opted to participate in games of roulette and blackjack at the casino, and according to witnesses who saw him in operation there, he opted to place a lot of his bets on red while playing roulette. However, he also opted to place long-shot bets on various single numbers, and while he continued to lose on these wagers, he just seemed compelled to keep playing even more.

This also led to further strains on his marriage to Coleen Rooney, and reports suggested that she had vetoed a potential transfer of the footballer to China. While she wasn’t present at the Manchester casino when he suffered that huge loss, Rooney did admit that when he was bored due to her not being around at times, he would resort to gambling. Perhaps Coleen should have been keeping a bit of a closer eye on her footballer husband and their fortune?

Birdman Vs. 50 Cent/AR-Ab ($1.2 Million)

50 centRappers are frequently known for flashing their cash around and showing off with it. So, it comes as no surprise that New Orleans-born rapper Birdman is also heavily involved with gambling as well. Being a lifelong New England Patriots fan, Birdman stated that he was ready to make a $5 million bet on the team during Super Bowl XLVI. Yet, the BetOnline sportsbook called his bluff and invited him to make the wager via its site. Birdman remained uncharacteristically quiet at that point, though.

Instead, he made a smaller $1 million bet on the same game against fellow rapper 50 Cent. Unfortunately, Birdman lost out on the wager, as the New York Giants came through with the victory in a 21-17 finish. And it seems as though Birdman didn’t learn his lesson from this occasion, as once the Super Bowl LII rolled around, he returned to Instagram and boasted about a $100,000 bet against Philly rapper AR-Ab. Subsequent posts followed this, which raised the overall total of that bet to $200,000.

Again, Birdman opted to back the Patriots while AR-Ab chose the Philadelphia Eagles as the winners of the Super Bowl. The Eagles stormed through to a victory with a 41-33 win, and this saw Birdman once again lose his large bet, meaning that two rappers have now taken $1.2 million of his money via sports betting.