The biggest disaster for the bookies which I know of happened in 1996 when I was working for a bookmaker. It was an amazing event which was awful for the bookmakers but truly fantastic for many punters.

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Frankie Dettori was a popular Italian jockey, well known for his likeable (despite being an Arsenal fan), cheeky character.

Each year, there are several days of horse racing in England at a course called Ascot. There are some important races and all of the top trainers and jockeys attend.

Frankie won the first race, then the second. His third ride managed to pip the well-fancied favourite to the post. The bookmakers were starting to get nervous. The horse racing experts would probably not have backed all of these four horses to win but Frankie’s fame among the Saturday morning, small-time punters always guaranteed that the “grannies” and armchair racing fans (of which there were many) liked to bet on his mounts.

Bookmakers like to encourage these small-time gamblers to do what they call multiple-bets. These involve backing several horses with small stakes with several different combinations and accumulators. If horse A wins, the winnings are put onto horse B to win. Horse B wins and the accumulative winnings go onto horse C to win and so on. Bookies love these bets as the chances of the punters winning big are tiny. The chances of the bookies getting most of the stake back are much larger.

When Frankie’s fifth ride came in, the small-time Frankie backers already had nice winnings guaranteed. After his sixth horse won, they were looking at very good winnings indeed.

At this point, bookies were going crazy with panic. They were already facing massive payouts.

When you place a bet, you can ask for the odds at the time of placing the bet. Fujiyama Crest, Frankie’s seventh mount in a seven race card was 11/1 in the morning with the firm I worked for. None of them expected the horse to win, but still, to be sure that they didn’t lose too much, the odds were cut to 2/1. Punters, however, were more optimistic and started betting on Fujiyama Crest to win. The bookies secretly laughed at the mugs betting on this relative outsider at such short odds.

And then, a few minutes later, the inevitable happened: Fujiyama hit the front of the field and scraped home by a neck to win.

Frankie had done the impossible: he became the only jockey to have ever won all 7 races on a 7 race card. Our big bosses were probably weeping at their desks but for those of us who witnessed this in the shops it was an amazing experience. The “mug” punters had won huge amounts while seeing horse racing history being made.

I must admit to being very happy to be giving the pensioners and “clueless” punters large cheques and big bundles of cash the following Monday. It made a change from paying the serious, miserable big time gamblers their winnings. The grannies coming in that day were incredulous and unbelievably happy. The bookies had suffered terribly but it was nice to watch them suffer for once, even though I was working for them.

My company lost around 8 million due to Frankie’s feat, the British bookmaking industry as a whole about30 million.

And just what were the odds?

The cumulative odds at the end of the race based on the odds the horses finished at were over 25,000/1. However, remember how I wrote that it’s possible to take the odds at the time of placing the bet? Anyone who had done this (and there were many who did) won around 236,000 for a 1 accumulator.

What a day!

27 Frankie Dettori’s Magnificent Seven

This answer originally appeared on this Quora question on Betting.

Top 10 Underdog Payouts In Sports Betting History

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everyone loves an underdog especially when it pays off in this video we’re counting down the top 10 underdog payouts in US sports betting history number ten prior to UFC 193 Ronda Rousey seemed invincible having won her last eight title fights in fact none of her past three fights lasted longer than 34 seconds so on November 14 2015 the fight community was stunned when Rousey lost her UFC bantamweight title to former champion boxer an 8 to 1 underdog Holly Holm knocking her out in the second round with a vicious kick to the neck number 9 the 1969 super bowl 3 was the first game to officially carry the moniker Super Bowl but it will forever be remembered for the guarantee Joe Namath quarterback of the 18 point underdog team New York Jets told reporters we’re gonna win the game I guarantee it Joe was right he led the Jets to a 16 to 7 victory over the Baltimore Colts stunning both football fans and odd makers alike number eight at the time Iron Mike Tyson was considered the baddest man on the planet with a record of 37 and OH and 33 knockouts Douglas was a 42 to 1 underdog and considered Tyson’s warm up fight for Evander Holyfield but no one told Douglas that and in round 10 he floored Tyson with a monstrous uppercut to become the new heavyweight champion of the world number 7 Man O’War is considered one of the greatest thoroughbred horses of all time during his illustrious horse racing career he won 20 of 21 races in almost a quarter of million dollars in purses who’d he lose that one race you asked the one hundred to one long shot appropriately named upset in the 1919 Sanford Memorial at Saratoga Man O’War who beat upset in there six previous meetings never lost another race number six it was only the Mets eighth season as a team in their first seven seasons the baseball underdogs had never finished better than ninth out of ten teams in the National League they held the record for the most losses with 120 in 1962 the Orioles came into the World Series 19 games ahead of second place and sweeping the championship series the Orioles lead game 5 of the 69 World Series 3 to 0 but still managed to lose 5 to 3 and take the six position on our list number five one of the biggest underdogs in Super Bowl history at 14 points the New York Giants made history in Super Bowl XLII the Giants entered the postseason is a wild card with a record of only 10 and 6 the Patriots on the other hand finished the season with a perfect 16 in all so both sports oddsmakers and fans were stunned when the Giants ended up beating the undefeated New England Patriots with a pair of touchdowns in the fourth quarter the last touchdown with only 35 seconds left in the game number four ranked fifth entering the season Michigan seemed unstoppable and was a huge 33 point favorite with oddsmakers in college football betting Appalachian State stunned everyone however with one of college football’s biggest all time upsets led by quarterback Armani Edwards and wide receiver Dexter Jackson the Mountaineers became the first division 1 double a team to beat a ranked tewevision 118 defeating the Wolverines 34 to 32 number three the United States is unbelievable 1 0 win over England in the 1950 World Cup has become known as The Miracle on grass at the time the English were considered the kings of football and heavy favorites with a record of 23 4 and 3 the American team had lost its previous seven international matches by a combined score of 45 to 2 and was composed of part time players most of whom who had other jobs to support their families the game’s only goal was scored by American center forward Joe gage ins number 2 do you believe in miracles everyone did after the u. s. hockey team beat the Soviet Union four to three in the medal round of the 1980 Winter Olympics the Soviet team comprised of seasoned professional players had won eight of the previous nine Olympic gold medals and had blown away the American college kids 10 to 3 in a pre tournament exhibition game just days before and the number one underdog on our list Alexander Karelin the three time defending Olympic champion in wrestling had never lost an international competition and was on a 13 year winning streak in fact Carolyn had not given up a single point in ten years in Olympic novice Gardner’s best previous finish an international competition had been fifth place and wasn’t even expected to contend for a medal what’s more Carolyn had just beaten Gardner three years prior five to zero but the twenty nine year old from Wyoming stunned the Russian and the world with a 1 0 victory in overtime to win Olympic gold in the greco roman heavyweight division and the number one spot on our list of biggest sports upsets in history you..

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