If you’ve seen Punch Drunk Love, then you’re familiar with the scheme of David Phillips, aka “The Pudding Guy”. In May 1999 he accumulated 1.25 million frequent flyer miles in a Healthy Choice Foods promo, even donating the food to charity for a tax deduction.
Stories like this fascinate me. I love when people figure out a secret hiding in plain sight, and win big. It’s the thrill of a bank heist but totally legal. They’re usually normal people who pay attention and think deliberately. Do you know any more like this? Here are some of my favorites.
Jerry and Marge Selbee, 80 and 81, made $26 million in the lottery over ten years. In 2003 Jerry realized he could almost guarantee a profit playing a lottery called "Winfall". Unlike most other lotteries, the jackpot rolled over to lesser winners every time it reached $5 million. Buy sufficiently many tickets then, and winning becomes probable.
Terry and Linda Kniess loved The Price is Right, and noticed many products were recurring. They memorized prices from every episode and attended the show. Terry was chosen to play, guessing the price exactly, then did it again in the showcase showdown, doubling his winnings to $53,473.
In 1984 Paul Michael Larson noticed the patterns on the Press Your Luck game show weren't as random as they first appear. He studied and memorized the patterns. Larson became a contestant, ultimately winning $110,237 (equal to $266,000 in 2018), over three times more than anybody had ever won on any game show.
Did you hear about sky-miles hackers and the US mint? People realized they could order currency from the mint, pay with their credit cards, and get free shipping. The physical coins were then shipped to their house or directly to the bank, with instructions to immediately pay off the card. They accumulated millions in sky-miles.
Maybe you’ve heard the story of the MIT Blackjack Team? It’s the basis for the book Bringing Down the House and two movies, 21 and The Last Casino. The story recounts how a group of MIT math students trained themselves in card counting and took to the Vegas Strip, winning millions.
It even works in sports. Prolific author and investor Tim Ferriss has also won several athletic titles, including the 1999 national Sanshou (Chinese kickboxing) championship. He realized you could win by TKO if an opponent left the ring three times in a match. He also noticed that nobody was using the weight-cutting techniques common in Greco-Roman wrestling. He cut weight, bulked after weigh-in, then pushed his opponents out of the ring. Judges didn’t like it, but there was no rule against it. He won every match by technical knockout, becoming the national champion after training for one month.
Clever gamesmanship can even take you to the Olympics. Skier Elizabeth Swaney analyzed the process for joining the Women’s Olympic Halfpipe team. Skiers must rank in the top 30 in several qualifying competitions. Swaney deliberately chose qualifying competitions with fewer than 30 competitors. By simply skiing without falling down, she registered a score and ranked. And despite her birthplace of California, she could claim Hungarian citizenship via her Hungarian grandparents. She joined the Hungarian team, not traditionally a serious competitor in the Women’s Halfpipe. Her 2018 Olympic performance was described as "perfectly mediocre". She barely attempted any tricks in either of her two runs. She placed last. The incident prompted the Hungarian Olympic Committee to reevaluate its selection process, and possible changes to the Olympic quota system.
She didn’t win medals. But she set out to compete in the Olympics, and she did. How many can say the same?
I’d love to gather as many of these as possible. They don’t have to be multimillion dollar schemes, though that won't hurt. These people aren’t cheating, they aren’t being dishonest. They’re just way way better at “the game” than anybody expects. What other stories are there?