Horse racing is a sport that encourages a wealth of different approaches from bettors. There are some who will always opt for low amounts, placing £1 or £2 on their favourites, sometimes choosing to splash the cash a little bit and make it an Each-Way chance. There are others who think much more carefully about their wagers, upping the stakes a wee bit and betting on an accumulator, hoping that it will bring the money rolling in if they get lucky. There are some, though, for whom small amounts just aren’t worth thinking about.

To be clear, the people that go big with their bets tend to have a huge amount of money in the first place. Our advice is always and forever to only place bets that you can afford to lose, which even millionaires need to follow. That is because what they can afford to lose and what the average person can afford to lose tend to be very different sums of money. They adopt the ‘go big or go home’ attitude and, unsurprisingly in the unpredictable world of horse racing, end up going home more often than not. The question is, what are the biggest bets we know of?

The Reasons The Whales Bet Big

Before we look at those big wagers that have been placed over the years, it is worth considering why it is that the biggest bettors, often called ‘whales’ in the industry, would bet such huge amounts of money. The obvious answer is that they are trying to increase the amount of money that they have to their names, but it is a little more complicated than that. Just as some banks will offer customers cash back on their purchases, so too are there some bookmakers out there who will give customers money back for betting with them.

These places, known to many as ‘rebate shops’, will offer as much as 5-10% back to the richest clients out there. It means that if they’re betting £1 million, they know that they stand to make as much as £100,000 of that back if the horse loses its race. Not only that, but they also know that, presuming that they’re betting in the United Kingdom, they won’t have to pay tax (directly) on their winnings. They can afford to lose the money and they stand to do very well out of it if they don’t.

From out point of view as the humble small bettor, the thing to bear in mind is that someone placing a huge amount of money on a horse is going to have an impact on the market. The second large sums of money are placed on one of the participants in a race, the bookies have to react and this usually entails them dropping the odds. They don’t want to risk too big an exposure, so something that looked appealing to us in terms of odds one minute might not look quite as good a few minutes later. There isn’t much you can do, but it is worth knowing about.

Kerry Packer’s AU$7 Million Bet In 1987

Perhaps the biggest ever bet placed on a horse race was placed in 1987, when Kerry Packer chose to wager AU$7 million on a horse that he owned that was running in the Sydney Cup. The Group 1 thoroughbred event was being run at Randwick Racecourse in the Australian city of Sydney over 3,200 metres, with Packer and his business partner, Lloyd Williams, confident in the chances of their runner, Major Drive. At least, that’s what many people thought. Williams was pleased to his odds drift as the race time grew closer.

Eventually, Major Drive went off with odds of 4/1, coming home well to win countless people large sums of money. One of those who was not amongst their number, though, was Kerry Packer. The ‘whale’ of Australian horse racing had placed many bets in years gone by, up to as much as AU$5 million, but he had had his head turned by the favourite for the race, Myocard. So confident was he that he decided to put the princely sum of AU$7 million, which was more than £4 million, on Myocard, ignoring his own horse.

In the end, Myocard came in second, meaning that Packer saw a return of AU$0 on his incredibly large bet. Whether he’d placed it with a rebate shop and at least got some of his stake back is unclear, but the bookmakers were doubtless delighted to have taken his money off his hands. When the winning jockey, Greg Hall, went to a ‘victory celebration’ at Packer’s home the evening after the race, he would have been forgiven for thinking that he wasn’t going to be well-received. Instead, Packer said, “I’m proud of you, even though I did lose $7 million on the second horse.”

Jim McIngvale Lost $1.5 million On The Kentucky Derby

You have to admire the intelligence of Jim McIngvale, better known to most as ‘Mattress Mack’. He launched a company called Gallery Furniture, believing that he could make a success of it if only he could get people to got to his store. He struggled initially, meaning that he was down to his final $10,000 and decided to invest it in a commercial to be aired on two local stations. When he didn’t like the advert being produced, he chose to take over the role himself and had to speak really quickly, desperate to fit all of the information into a short space of time.

The ad was a hit, resulting in people turning up to his store and spending big sums of money there. Soon, he needed to find a different way of getting people to spend their money in his stores, so he 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 end up losing anything because of this, he placed sizeable sums of money on the outcome that he’d made his offer for.

In 2022, for example, he offered money back if the Cincinnati Bengals won the Super Bowl. In order to ensure that he wasn’t out of pocket if that happened, he placed two bets totalling $9.5 million on the Bengals, only to see he Los Angeles Rams emerge victorious in a close-run contest. Similarly, Mattress Mack bet $1.5 million on the favourite for the Kentucky Derby, only to see it miss out because of the longest-odds horse in the race, Rich Strike, coming in first with odds of 80/1. A big loss, but good publicity for Gallery Furniture.

$200,000 Placed By Bill Benter

In some ways, this is a bit if a cheat on this list, insomuch as Bill Benter didn’t place the $200,000 all in one go. That being said, what he did do was line himself up to be in position to be as good as guaranteed a return of $16 million through the bets that he placed, so it feels like a ‘cheat’ that is worth allowing through. In spite of the fact that Hong Kong had returned to the control of the communist government of China, horse racing was still allowed in the country in 2001, with the Happy Valley course being a popular place to go.

In order to appeal to bettors, the course offered not just a Trifecta, whereby punters had to pick the top three horses in a race in the correct finishing order, but also do it in three separate races. This bet, called the Triple Trio, was so popular that the jackpot for winning it crept up to $16 million. Rather than chancing his arm on luck, Benter worked out a complicated handicapping algorithm that revealed the only horses that were likely to have a genuine chance of winning the three races, figuring that there were 51,000 possible combinations.

Working with a partner-investor, Benter placed in excess of $200,000 worth of bets on the 51,000 combinations for the Triple Trio, striking gold when one of them came in. Rather than cashing in their winning Triple Trio slip, however, the pair instead had their photo taken with it and then locked it in a safe. Knowing that the winning money would be given out to good causes if it went unclaimed, Benter wrote a letter to the Hong Kong Jockey Club informing them that he was the holder of the winning ticket, but that he had no intention of collecting it.

JP McManus’ £100,000 Became £600,000

If you’re a multimillionaire who understands horse racing like the back of your hand, it is probably a little bit easier to risk huge sums of money than if you’re just some idiot who goes off the colours the jockeys are wearing or the names of the horses. JP McManus definitely fits into the former category, with the Irish businessman and race horse owner heading to the Cheltenham Festival in 2006 with a plan to put his money where his mouth was. That was thanks to the fact that he had a horse running in the first race on Day Three of the meeting.

Reveillez was lined up to run in the Jewson Novices’ Handicap Chase, a Listed event at the time that was run over two and a half miles. During the course of the event the horse had to contend with 16 fences, which wasn’t easy when you consider that there were 18 horses in total looking to get to the finish line first. The good news for McManus was that he had a not-so-secret weapon in the form of Tony McCoy riding Reveillez, giving him about as close to a cheat code as it is possible to get in the world of thoroughbred horse racing.

Rich and confident is a dangerous combination for a punter to have if you’re a bookmaker who is willing to take big bets. As far as Freddie Williams was concerned, though, there’s a reason his nickname was ‘Fearless’. He was known for being willing to take six-figure bets and he did just that when McManus turned up with £100,000 to place on his own horse. The bet was placed and Reveillez did exactly what his owner expected him to do, romping home at odds of 6/1 to give the Irishman £600,000 in profit and £700,000 overall.