Luck is a tricky a thing; sometimes it’s on your side and sometimes it’s on the house’s side. The only problem with this concept is you never know whose side luck is currently on. Usually the bigger the the risk the bigger payout right? Unfortunately, this isn’t always true. Below are some stories of miraculous wins, and unbelievable losses and everything in between. These stories will definitely make you think twice when placing your next bet at any sports betting sites.

The Story: In the summer of 2009, the Delaware Senate passed a controversial piece of legislation. In order to help offset their state’s nearly 800 million dollar budget deficit, and with a little prodding from the governor Jack Markell, the senators made the nearly unanimous decision to allow, and tax, limited sports betting throughout their state. It was hoped that the move would generate roughly $50 million dollars in the first year alone.

One fortunate man (whose name has not been released) living in Delaware decided to make good use of this freedom. The man made his way to the local sportsbook, The Dover Downs, and purchased two tickets. One cost him $100 and the other cost him $20. Both were ten-team parlays. In order for a ten-team parlay to pay off, you must make a pick of ten different teams playing on separate occasions against separate opponents. Every single one of your picks must win. If even one of your teams loses you win nothing. Those are some rough odds.

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More specifically, the odds of you picking the right team every time (assuming the chance is fifty fifty for each game) are about 1 in 1,024. Which means that any gambling institution would be happy to offer you, say, 960/1 odds. Which means if you bought a ticket for $100 dollars and somehow you won, you would end up with. . .

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That’s right. Our anonymous hero chose ten different winning teams and went on to win $96,000, only a couple of months after gambling was declared legal. In terms of sports gambling $96,000 isn’t an enormous amount, but the fact that it only took this guy two months to sucker punch Delaware in the money bags makes him cool.

The Story: Choosing ten different teams correctly at the same time is clearly not easy. We’ve established that. And for people that want to take it even one step further, the fifteen-team parlay offers a stupidly difficult bet to win. But for some people, “stupidly difficult” isn’t enough. For some people, only the ridiculously, unspeakably, Jesus-stumpingly difficult will do.

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People like that are really left with two options: either move to Britain, or just kick ass on every American bet you can find. One Las Vegas resident (who also did not want to release his name) decided to try just that.

The man had already bested the ten-team parlay, which officially makes him a gambling hero, and was looking for bigger game. He found a casino that offered the fifteen, laid down his money, and went about his business. He only actually paid five dollars for the ticket, but we’re going to assume that he just understood on some level that he only needed a five dollar bet to make us all feel like dumbasses for spending our money on food.

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Every day afterward more of his picks came in winners until, in the end, he was left with a winning, fifteen-team parlay ticket. He turned it in for $100,000, did the hundred thousand dollar dance, and probably moved to Britain.

Nebraska Fumbles

The Story: Billy Baxter is a big name in gambling. An inductee into the Poker hall of fame, winner of several large Poker tournaments, and a notable sports bettor as well, Billy Baxter is a big name.

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Mostly this is because the man has made about $2,100,000 in tournament money over the years and has seven poker world series bracelets, but it’s also because he is notoriously good at winning bets that he really ought to lose. Like the one he placed on the 1984 Orange Bowl.

The Nebraska Cornhuskers were an undefeated, universally feared football phenomenon. They had already embarrassed most of their opponents, putting seven touchdowns on the board in one quarter against Colorado, and were looking for blood. Miami was none of those things. So, obviously, Mr. Baxter put $10,000 on Miami.

The game was a tight one. Miami grabs a lead in the beginning and fights hard to keep it the rest of the game. The Cornhuskers fight back, however, and by the end of the fourth quarter are only down by seven. With under two minutes left in the game, Nebraska moves the ball within thirty yards of Miami’s goal and then runs three unsuccessful plays, putting them at fourth down and eight. Suddenly, out of the backfield comes Turner Gill, the quarterback, apparently running himself. Just as he takes a hard hit and falls, we notice the option, and the back with the ball charging down the sideline. One 24 yard run later, Nebraska is only down by one.

At this point the game is Nebraska’s. They only need to score the extra point to tie the game and cap off one of the greatest seasons of college football ever. Unless there was some kind of more complicated, extremely difficult way to earn two points instead of just one. It’s not like earning two points instead of one would have any impact on anything, but then they wouldn’t have to just settle for a tie.

Nebraska gave up the kick and ran the two point conversion. It didn’t work.

1984 went down as a public humiliation for Nebraska. What should have been theirs slipped away with one bad call. But, on the bright side, Billy Baxter made off with $130,000. Some people are a big deal for a good reason.

King Cadmus

The Story: Back in the late eighteen hundreds there weren’t a whole lot of recreational opportunities. You could sit quietly in your rocking chair, or whittle, or shine your shoes for Sunday service, but aside from that, the only fun to be had in 1890 could be found in the bars or at the horse races.

George Ellsworth Smith, better known as Pittsburgh Phil, understood this concept. The man was a long time gambler of the horse races, and was known to spend several days and hundreds of dollars (a lot of money at the time) at the tracks at a time. One day, Phil decided, as so many great gamblers one day do, “why the hell not?” and put over a thousand dollars (really a lot of money at the time) on a wimpy, underdog horse named King Cadmus for 10 to 1 odds.

Now the thing about “why not” is that it doesn’t pay off very often, but when it does pay off it pays off like a Colombian cocaine empire. When King Cadmus made it first past the post Phil collected a whopping $143,000. Adjusted for inflation, that equals roughly $3,384,629.49 today. We like to imagine that he used the money to get people to stop calling him Phil when his name was George.

Queensland Backfire

The Story: Whether we Americans want to believe it or not, rugby actually attracts a lot of attention in some parts of the world. The governments of Scotland, New Zealand, Wales, Australia, and South Africa, among others, all acknowledge Rugby as one of the most popular sports in the country. We assume this is why:

In fact, one European man actually loved rugby enough to place a $700,000 bet on his team, the Queensland Maroons, to win at the famous rugby match called the Origin Opener. The maroons were heavy favorites in the match and I’m sure the man was excited to just sit back, enjoy some warm beer, and make a few thousand dollars while watching his team.

Instead, the man got to sit back with his beer and watch as his team was absolutely dominated by the underdog. New South Wales came out fiery, and by the end of the game was ahead by eight points. Sure, the loss was disappointing for Queensland, but for the guy who lost $700,000 on a sure bet, it had to be devastating.

A Lot For A Little

The Story: There’s almost nothing better than getting something for nothing. Buying a pizza with your friends for five bucks is fun. Pretending you forgot your wallet and getting your friends to buy a pizza for you is even better. Going out and renting a DVD is fun. Staying home and downloading that DVD on bit-torrent is even better. See the pattern?

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If you can’t get something for nothing, however, your next best bet is to get something for almost nothing. That pizza is still going to be good if you have to donate the change in your pocket, and that DVD is still going to be fun to watch even if you have to shell out a dollar to a Redbox somewhere. The same applies in gambling. You’re never going to find a casino that wants to pay you for nothing. The best you can hope for is luck like Ron Nicholson’s.

Mr. Nicholson, probably without hardly remembering he did it, once bought a four pound ticket for the Tote Scoop 6 race. That’s a four pound ticket. In London they make four pound bets on whether the toast will burn in the morning. The only thing they have more of in Britain than four pound bets is Harry Potter impersonators.

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So when Mr. Nicholson found out that his ticket was a winner, we doubt he was too excited. After all, how big can you win with a four pound bet in London? Apparently, really really big. For his modest investment of four pounds, Nicholson walked away from the tracks with nearly a million and a half dollars. A million and a half has never seemed so cheap.

Saved By The Spread

The Story: If you’re going to put up a solid million dollars for any kind of bet, you had better know what you’re doing. You need to really understand what you’re betting on, you need to really understand whom you’re betting against, and you need to really understand the very nature of gambling.

Bob Stupak understood. As the owner of several casinos, builder of the Stratosphere, and long-time Vegas player, Stupak understood gambling just as well as almost anybody. So when Superbowl 23 came around and Stupak decided to lay a million dollars on the Bengals to come up with a win, he wasn’t too worried by all of the second guessing and scared attitudes around him. He had a good spread, he knew the team was up to it, and he could feel it was time. He wasn’t worried.

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In the end, the Bengals lost the game. Joe Montana and Jerry Rice on the same team were simply too much for Cincinnati to handle and, with a historic last quarter push, the 49ers beat the Bengals by four points. For most of us, putting a million dollars on an underdog team that loses by four points in the last three minutes is justifiable grounds for sobbing like a twelve year old with crack withdrawals. But Bob Stupak wasn’t worried.

You see, Bob really knew what he was doing. Before the game even started, he had set himself up with a nice enough spread that four points didn’t mean to him what it would to us. Bob still walked away with a million dollars in prize money, after betting on a losing team. No wonder the guy’s never worried.

Risky Business

The Story: There are only two situations in which taking an enormous risk can be rationally justified. The first situation is one driven by necessity. If every possible outcome of doing nothing is worse than the consequences of taking the huge risk, then you have nothing to lose. The other situation is one driven by greed. If the possible payoff of the risk is big enough, then it may be worth taking.

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Obviously gambling is the kind of risk that’s driven by greed. You don’t lay down the dollars unless you think that somehow you might make a whole bunch of money. This is why people tend to avoid really difficult bets, but it’s also why we avoid the overly easy bets as well. There’s no sense in risking my ten dollars for the possibility to win twelve dollars no matter how good the odds are. I’d only be making two dollars, and there’s a chance that I could lose my ten dollars. It’s just not worth it.

Now multiply that example by 240,000. That’s what it would take for you to put, like one anonymous man did, 2.4 million dollars on a bet that could only win you about $300,00. That’s not to undersell 300,000. Anybody would love to have $300,000.Most people would trade the hot Hermione up above for the $300,000. But the fact is, the chance to win $300,000 is just not worth the chance to lose a 2.4 million.

The man did actually win, as everybody expected him to, so I suppose we should keep our mouths shut, but the moral of this story is obvious: even if you look like a smoking hot young actress, most people will still sell you for $300,000.

Go Big!

The Story: Remember how we already talked about how New Zealanders like rugby? Well, it turns out that I somewhat understated the case. Apparently, New Zealanders sincerely and whole-heartedly love rugby.

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: And they have good reason to. Their team, the New Zealand All Blacks, is one of the fiercest, most terrifying rugby teams in the world. They consistently are ranked number one in the world and they start every game with the same bone-chilling tribal ritual:

So when one anonymous New Zealander placed $4.2 million dollars on the All Blacks to come up winners at the 2007 World Cup, I doubt it was a gamble in his mind as much as it was just a demonstration of confidence. A very expensive demonstration of confidence.

During the first match, the man’s faith seemed well placed. The All Blacks erupted out and slaughtered the Australians. Both spirits and hopes were high as the team made its way into the second match.

And then things started to fall apart. Known for their ability to choke at the most inopportune times, the All Blacks felt that they couldn’t disappoint the fans. Seven minutes into the second game New Zealand had already given up easy points to the other team. By the end of the match, after several more catastrophes, the whole world was laughing at New Zealand. You see, the most feared rugby force on the planet had lost to France.

The man lost his $4.2 million dollars. Because his unstoppable team of blood-thirsty Maori warrior lost to the French. You gotta wonder when it’s time to give up and move to Australia.


The Story: So here we are. The ultimate sports betting story. And it begins, just as you might expect, with a man who didn’t really understand “odds,” “probability,” or “not ever ever going to happen in a million years.”

This anonymous bettor was not interested in ten team parlays. He wasn’t fazed by fifteens. He just wasn’t concerned with all of the “ordinary” impossible bets. So instead he went and found a casino that offered him exactly what he was looking for: an absolutely sure way to lose money.

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What the man found is called a Canadian, or a Super Yankee. For explanation purposes, understand that a “double” is a two-team parlay. A “treble” is a three-team parlay and a “four-fold” is a four-team. A Canadian, then, is a combination of 10 doubles, 10 trebles, 5 four-folds plus an accumulator. You read that right. The Canadian is insanity.

But, from a cozy padded room somewhere, our anonymous hero got to watch as his insanity paid off. One team after another, good pick, good pick, good pick. . . . it was a good day to be nuts.

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In the end the lucky man won over five million dollars. It is still considered one of the most astounding bets of all time, and has surely inspired tons of copycats. Unfortunately, only real crazy is that lucky.