The world of horse racing has enough incredible stories on the track to cover a dozen articles like this. But fewer are the incredible stories of crazy bets. Across the world, millions of bettors regularly bet small amounts – which is the backbone of the business. Few horse race bettors ever reach the point of putting down or winning millions on the races, and even less make the kind of incredible bets to go down in history.
But these people prove some can do it. From a stable-owning mogul who list millions backing his own horse, to one of the most successful horse racing bettors of all time who sparked international news in Hong Kong to a lucky man who turned pennies into millions on a parlay – these are three of the most skilled, richest and luckiest horse racing bettors ever to play the game.
Bill Benter Won $13 Million on the Races and Never Claimed It
Bill Benter is one of the most successful sports bettors of all time. The American did not, however, make his fortune off the backs of Las Vegas gambling operators. He instead, won his significant fortune betting on horses in Hong Kong.
While based there in the early 1990s, Benter made upwards of $10 million betting on the races, after already making a few million on the tail end of the Las Vegas card counting boom.
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Benter’s most famous bet however was one he never claimed. Shortly before upping sticks and heading back to the USA, Benter put his computer algorithm towards the Happy Valley Racecourse’s jackpot prize. Predict the top three horses in the day’s three headline races, and win the jackpot starting at $2 million. The jackpot had rolled over six times without a winner, and Benter put down $200,000 on his picks – which would net him a cool $13 million.
But he already knew he was leaving Hong Kong that week, and never intended to claim it. He, of course, won, and the anonymous win was one of the most talked about mysteries in horse racing for decades. Until Benter confessed in later life. Hong Kong racing authorities eventually decided to donate the money to charity.
Kerry Packer Bet AU$7 Million Against His Own Horse
In 1987 famous Australian gambler and media tycoon Kerry Packer caused turmoil at the races when put $7 million down on the un the largely unknown Myocard to win the Sydney Cup. However, despite causing a seismic shift in the market, another horse that Packer actually owned (that he hadn’t bet on) won the race.
The Group 1 thoroughbred event was scheduled to run at Randwick Racecourse in Sydney, Australia, over 3200 metres. Packer owned the horse Major Drive, which was an outside favorite going into the race. However, rather than bet on his own horse the maverick bettor put down $7 million on Myocard.
Many have speculated as to why, but Packer has never spoken on it since. Or at least, publicly. Myocard did come second, so it is possible he placed a bet in which he got some of his money back – but no-one officially knows.
Some people did make good money on Major Drive though, whose odds lengthened dramatically after word of Packer’s big bet on a rival horse caught the attention of the market.
Packer went on to gamble some $50 million over the next decade, with his high stakes wins and losses significantly affecting the turnover of several major bookmakers. He continued to gamble for the rest of his life but clearly either won more than he lost or kept it within his (prodigious) budget, as he was estimated to be worth several billion at the time of his death in 2005.
British Bettors Turns 20 Cents into $1.5 Million
Englishman Fred Craggs made one of the most remarkable horse betting wins ever back in 2008. Craggs, from Thirsk, Yorkshire, but 50 pence (around 20 cents) down on an eight horse parlay bet at his local William Hill betting shop.
He also picked his horses in whimsical manner, choosing horses called Isn’t That Lucky and a Dream Come True, amongst others. At odds of 2.8 million to one, Craggs stood to win £1.4 million. All eight then won their races, netting Cragg one of the biggest wins in horse racing history.
Interestingly, at that time William Hill capped single bet wins at £1 million without preapproval so he only actually won £1 million (around $1.33 million) at the time.
To top it all off? The day after the race, when Craggs claimed his money, was his 60th birthday. Some story.