10 People Who Won the Lottery More Than Once (5 of 6)

Stefan Mandel: 14 wins

For Stefan Mandel, winning the lottery is like an engineering problem. In 1992, he won a whopping $27 million jackpot on behalf of an Australian syndicate by doing something simple in concept and brutal in execution: buying every possible number combination. At that point, there is no room for luck. And that win wasn’t even his first. According to the reports, the big jackpot was his 14th win. You can only imagine how much planning, research, and logistical nightmares that operation was. Unfortunately, modern lotteries have so many combinations that buying them all is not an option.

Armand Paganelli: 16 wins

Armand Paganelli, a Bronx businessman, made headlines for buying 16 winning lottery tickets in 2013-2014. The tickets were purchased at a drugstore he owned and ran with his brothers, which naturally made people suspicious. But it’s legal for retailers to buy tickets from their own store, and Paganelli’s total haul landed around $625,000. He’s been pretty straightforward about it: he likes to gamble, so he buys a lot of tickets. And when the wins came, he used the money in ways that sound less flashy and more real-life responsible, like helping with his kids’ college and giving to charity.