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The Romanian mathematician who bought every combination
Stefan Mandel worked out that if a jackpot exceeds the cost of every ticket, you just buy every ticket.
Mandel's insight is almost insultingly simple. A lottery with, say, 7 million possible combinations and a $27 million jackpot is a thing you can buy outright for $7 million, if you can physically fill in and pay for that many tickets.
The hard part is logistics, and he spent years on it: investor syndicates, printing operations, and armies of couriers. He did it in Romania, then in Australia, and in 1992 took the Virginia state lottery with a syndicate of around 2,500 investors.
They managed to buy roughly five million of the seven million combinations before the shops physically ran out of time, and got lucky that the winner was among them. The jackpot was about $27 million.
It was investigated by several agencies and found to be lawful. Lotteries then rewrote their rules — bulk purchase limits, no printing your own slips in volume — specifically to stop it. You could not do this today, which is rather the point.