Trying to explain to someone who just doesn’t get it why you love sports is a tall order. We know we connect with the players in some primal way, but it’s not easily put to words. There is also something to be said for the way we can relate to the soul-crushing defeats and extreme highs that accompany every team over the long run.
Sometimes, only compelling reason to watch a perfectly mundane match is for the off chance that you see history in the making. That perfect game, first round KO for the underdog or opening goal in what will be a fairytale season for your city’s football club can all happen at any time with no warning.
Online bookmakers love to tempt us with wagers that mirror these longshot outcomes. Both they and us know that the odds of the Kansas City Royals clinching the World Series or Leicester City capturing the Premier League title are so unlikely that it’s almost not even worth thinking about. Almost.
Every once in a great while, history is made and the bookmakers have to pay outrageous sums of money to those stubborn courageous enough to back outcomes that have almost no shot of happening. The payouts are so large and so unexpected that the lucky punters themselves are just as likely as the players to make the news.
5. Vegas Dave and the Kansas City Royals
- Total wagered: $100,000
- Payout: 25/1
Back when most projections had Kansas City pegged as a sub-.500 team in early 2015, David Oancea saw things differently. He saw things so differently, in fact, that he went ahead and put down $100,000 worth of futures wagers on the Royals winning the 2015 World Series. He got in early while the odds of a KC win were in the range of 30/1 and singlehandedly pushed the odds down as he continued pounding on the Royals win.
As history would have it, the Royals would once again defy the odds and make it to their second consecutive World Series. This time, they won it in five games. Very few people saw this coming, and only Vegas Dave found the odds attractive enough to drop a six figure bet on the outcome.
David Oancea, better known as Vegas Dave, is a professional sports bettor who has a reputation for making bold picks and backing them with serious money. He also publishes pictures of his winning slips as proof that he puts his money where is mouth is. The Las Vegas Sun reported that the bookmakers even offered him a guaranteed $750,000 payout at one point if he would call it early. He chose instead to let it ride and cashed in for a grand total of $2,457,200.
4. Super Bowl XLVIII Safety Nets $50,000 Payday
- Total wagered: $500
- Payout: 50/1
Safeties are relatively rare in the NFL and only nine of those have ever happened during a Super Bowl. That works out to an average of one safety for every 5 ½ Super Bowls. The odds of a safety happening on the very first play of a Super Bowl are ridiculously long. However, that is exactly what happened in Super Bowl XLVIII between the Denver Broncos and Seattle Seahawks.
A few online and real-world bookmakers also offered a “first score is a safety” proposition bet before the game with odds of around 50/1. It is hard telling how many people took up the bookmakers’ offers online, but we do know of one Jona Rechnitz who placed that exact bet for $500 at the MGM Grand sportsbook in Las Vegas. His business partner took the same bet for $300. Their winnings netted a grand total of $40,000 between the two of them.
3. Vegas Dave Strikes Again with Holly Holm
- Total wagered: $20,000
- Payout: 11/1
Just two weeks after winning $2.5 million on the back of the Royals winning the World Series, Vegas Dave struck again with another outlandish wager. Showing his versatility, Vegas Dave’s next big bet came on the much-anticipated matchup between longstanding UFC champion Ronda Rousey and Holly Holm. He laid $20,000 on Holly Holm at 11/1 odds and ended up taking home another $240,000.
What makes this bet crazy is that Ronda Rousey was such a dominant fighter at the time. She had a perfect 12-0 record with 11 first round finishes and 1 third round finish. Nine of her fights were over in under a minute. She seemed unstoppable and few gave the relatively unknown Holly Holm much hope.
Fight night came and Holly Holm stunned the world with what was arguably the biggest upset in the history of the UFC. Sure, there was some speculation that Holly’s venerable boxing and kickboxing experience could give her the keys to victory, but not too many people predicted what actually happened inside the Octagon on that night. Holly Holm made the reigning champ look like an amateur. It was ugly.
2. 30p Bet Wins £500,000
- Total wagered: 30p
- Payout: 1,666,666/1
The mother of all accumulators was won back in 2001 after an anonymous William Hill customer turned a 30p into £500,000. The 15-leg selection included wagers on football, rugby and cricket matches with odds totaling 1,666,666/1. His historic payout remains the single largest successful accumulator known to anyone.
For those who don’t know, an accumulator bet (or a “parlay” by American terms) allows you to receive enhanced odds if you pick the outcome of multiple matches. Accumulators tend to offer the highest odds in all of sports betting, but they come at a cost. You must get every selection right to win the bet. If just one of your picks is incorrect, you go home with nothing.
Another punter more recently came extremely close to landing a successful 22-leg accumulator with Betfair. He paid £49.50 and made 22 selections for a chance to win roughly £1.5 million. He ended up cashing it in early for a more modest £53,000 payout just before the 18th leg. It’s a good thing he did, because as the Daily Star reported, the 18th leg would have cost him everything.
1. Leicester City’s Fairytale Run
- Total wagered: Unknown
- Payout: 5000/1
Leicester City began the 2015/16 season as 5000/1 longshots to win the Premier League that year. They had only recently been promoted back to the Premier League and barely managed to escape relegation the previous year. To call Leicester City underdogs at that point would be to give them too much credit.
Most UK bookmakers were all offering 5000/1 for anyone brave enough to back Leicester to win the title at the beginning of the season. Some punters did indeed take the bookies up on the offer and were rewarded handsomely after Leicester did the unthinkable.
Even before Leicester sealed the deal, news began breaking that the bookmakers stood to lose millions. Multiple big-name betting sites such as Bet365, William Hill and Ladbrokes each admitted that they were on the hook for upwards of £3,000,000. Some bookmakers even began calling customers who had open bets on Leicester and offered to settle the bets early at a discounted rate.
Ladbrokes revealed at one point that they had taken 47 bets on Leicester at the beginning of the season. Some gamblers wagered as little as 10p (good for a £500 payout); while others bet middling amounts in the range of £5 (£25,000 payout) and £10 (£50,000 payout).
Another punter backed them for £50 at the beginning of the season and stood to win £250,000 until his bookmaker called him to renegotiate as the end drew near. Not wanting to test his luck any further, the anonymous punter took an immediate £72,000 payout.
Never in history has such a betting underdog come through like Leicester City did in the 2015/16 Premier League season. This was truly a sports bet for the ages. The best part of all is that it came through for a whole lot of punters.