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There aren’t many feelings better than winning a bet at the races. Betting at the racetrack has been a long-practiced leisure activity throughout the sport’s modern era but with the emergence of online betting, the thrill of winning big has been taken from the course to the comfort of your own home.
The improved technology has not only provided greater accessibility to sport but has also introduced the possibility to push the boundaries of ordinary sized wagers. Big returns are yielded with each year that passes as the allure of winning at the races continues to entice the high-rollers.
For some though winning big isn’t enough. These punters wanted to win enormous and whacked down some massive sums of money in trying to do just that. Here’s our look at some of the biggest bets in horse racing history.
JP McManus – £100,000
When the Irishman businessman turned up to the third day of the 2006 Cheltenham Festival it became clear very quickly that there was more on his mind than just the performance of his thoroughbred, the seven-year-old gray gelding Reveillez ridden by Tony McCoy.
McManus was determined to put his money where his mouth was. Reveillez was due to run in the first race of the day, the Jewson Novices’ Handicap Chase, a grueling event that was run over two and a half miles, featuring 16 fences with 17 other competitors across the field.
Thankfully McCoy is to date one of the greatest riders of thoroughbreds in the history of the sport and he would prove that once again on this day. Betting sites like horseracing.net always offer up odds and sometimes punters are more than happy to tackle them, but McManus was after something else on this occasion. Confident in his horse’s chances JP sought out notorious bookmaker Freddie Wiliams, nicknamed ‘Fearless’ and with good reason.
Well-known amongst the high-rollers for his willingness to take six-figure bets, this was one such instance with McManus opting to place £100,000 at 6/1 on his horse to win. Reveillez delivered, romping home for the win and a healthy sum of £600,000 in profit for his Irish owner.
Bill Benter – $200,000
We’re bending the rules a bit for this entry as Benter didn’t actually place his $200,000 bet in one hit but the nature of his victory makes it worthy of mention on the list. Despite Hong Kong recently returning to the control of the communist Chinese government, horse racing was still permitted in the country with the Happy Valley racetrack proving one of the most popular venues of that time back in 2001.
As a means of drawing in punters, the course had a special deal offer, not just a Trifecta where bettors had to pick the top three horses in a race in the correct order, but something called the Triple Trio. This was an offer where those looking to chance their arm with the Trifecta would have to do so over the course of three separate races.
The deal was so tantalizing to the visitors of the racetrack and so difficult to pull off that the jackpot for winning it had soared to $16 million. Benter saw this as a prime opportunity to capitalize on. Alongside a partner/investor, Benter devised a handicapping algorithm that identified out of the 51,000 possible combinations the only horses that were likely to have a genuine chance of winning the three races.
The American applied his method by spreading his $200,000 across all those potential combinations and in doing so all but guaranteed the $16 million win. Stranger than the calculation process though was his actions after claiming victory.
Rather than cashing in their winning Triple Trio slip, the pair instead had their photo taken with it and then locked it in a safe. Benter went on to state he had no intention of claiming the prize in the knowledge that if left unclaimed the money would be donated to good causes. Clearly a man with money to spare.
Jim McIngvale – $1.5 million
Jim McIngvale, known to many as ‘Mattress Mack’, is not only the owner of thoroughbred stallion Runhappy but also the founder of the Gallery Furniture chain of stores across America. While that has put him on the map, what has caught the attention of the racing world and the sports betting world overall is his outrageously large bets.
In 2022 though, in his own unique way he decided to combine his two worlds. The businessman came up with the idea of attaching offers to sporting events. He promised customers that if something happened, such as the favourite in a race winning, they would get their money back.
In order to ensure that he didn’t come out on the losing side of this, he decided to insure himself by betting a massive $1.5 million on the favourite for the Kentucky Derby, Epicenter. His plan backfired in epic fashion.
Not only did Epicenter fail to win, he lost out to the longest shot in the field, Rich Strike, who started the race with odds of 80/1. It undoubtedly would have stung but McIngvale is no stranger to this kind of feeling having lost $9.5 million on the 2022 Super Bowl. It’s not all doom and gloom for Jim though, at the very least it’s some incredible publicity for his furniture company.
Kerry Packer – $7 million AUS
To round out our list is racehorse owner Kerry Packer who currently holds the record for the biggest bet in the history of horse racing. In 1987, Packer and his business partner, Lloyd Williams, had their runner, Major Drive, featuring in the Group one thoroughbred event at Randwick Racecourse in the Australian city of Sydney over 3,200 metres.
He was in contention at 4/1 odds before the race but Packer’s attention was elsewhere. The favourite for the race was Myocard and Packer was so confident in his opposition’s chances that he decided to put a whopping $7 million AUS down.
The Australian was left with egg on his face as his own horse jockeyed by Greg Hall went on to win, while Myocard came home in second place. He saw no return on his bet and despite putting on a brave face when facing Hall at his home that evening, there is little doubt the businessman would’ve been deeply regretting his decision.
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