In the 1990s, Romanian-Australian economist Stefan Mandel and his small team entered the lottery and won. Over and over and over again.
The feat, of course, wasn't achieved through having a really lucky set of numbers. Mandel had a system, which he first put to use to win a lottery in Romania, using the money to bribe officials and head first to Europe then to Australia.
The odds of you winning the lottery are pretty low. The chance of you winning the EuroMillions jackpot with one ticket, for instance, is 1 in 139,838,160. Say you decided to double your chances by purchasing another ticket, you'd still only have a chance of 2 in 139,838,160.
You'll notice, though, that assuming you can buy more of those combinations eventually you will reach a point where your odds are 139,838,160 in 139,838,160. Now instead of a math problem you have a logistical problem: getting your hands on 139,838,160 tickets, without having already won the jackpot.
Mandel noticed, according to The Hustle, that in certain lotteries the jackpot prize rose to more than three times the cost of buying up every single possible combination of the lottery. Assuming you could buy every combination of numbers, you were (almost) guaranteed a return on your investment (assuming that several regular players don't win with the same numbers, splitting the pot). Mandel essentially decided to do this.
Though not against the explicit rules, it wasn't exactly in the spirit of the game. The problems, though no longer mathematical, were still not small. He first had to convince enough investors to buy into the scheme, which he achieved over several years. He then had to figure out a way of purchasing every possible combination in whichever lottery they were entering. Considering they could be entering millions of different combinations, this required him to create algorithms to generate then print the tickets (which some lotteries allowed at the time).
With a stack of tickets printed and ready to go, then came the matter of waiting for a big enough jackpot, at which point the team would purchase those tickets in shops. Even then, given the sheer bulk of tickets involved, it didn't always go smoothly, as was the case in Virginia.
Having cleared up in multiple smaller lotteries in Australia, Mandel spotted lotteries in the US whose jackpots vastly outweighed how much it would cost to purchase every combination. Of particular interest was the new Virginia lottery, which only used numbers 1 to 44 in its draws. This meant that there were 7,059,052 possible combinations, far fewer than the usual 25 million or higher.
When the jackpot was high enough – $15.5 million – he ordered his team on the ground to buy the tickets in bulk. Mandel had of course pre-arranged the unusual purchase, rather than letting them walk in with a stack of tens of thousands of tickets and tell the gas station attendant, "I hope you take hundos". However, some pulled out of the arrangement, leaving ticket combinations unpurchased.
After two days of purchases, Mandel's team had purchased 6.4 million of the possible 7 million combinations needed to guarantee a win. Though tense, they did have the winning ticket in their unreasonably large pile of losing tickets.
Though he was investigated by the FBI and CIA, no wrongdoing was found. In total, Mandel won 14 different lotteries, bagging millions of pounds of prize money for himself and his investors, before retiring to a beach house on the tropical islands of Vanuatu.