Con Men, Grifters, and Hustlers: 5 of the Greatest Schemes of All Time

Business Insider

5 – David Phillips and the Pudding Scheme

Although Phillips did not commit a crime, his ‘Pudding Scheme’ deserves mention on the list for its brilliant simplicity. He found an insane flaw in a promotion offered by Healthy Choice in 1999. The company offered up to 1,000 air miles to customers for every 10 product barcodes they sent to the organization.

Phillips is an engineer and the kind of person who enjoys scouring the small print for loopholes in offers such as the one provided by Healthy Choice. It didn’t take him long to see the potential in the barcode offer, so he quickly searched for the cheapest Healthy Choice products. He hit the jackpot by finding a discount grocery store chain that sold individual chocolate pudding cups for just $0.25. Therefore, Phillips knew he could earn 1,000 air miles for just $2.50! In fact, the original promotion was 500 miles for 10 codes, but the company had an ‘Early Bird’ special whereby customers would receive double air miles for redeeming their coupons within the first month.

Phillips didn’t hesitate and purchased every single pudding cup he could find. When he was finished, he spent $3,140 and benefited from over 1.2 million air miles with a value of approximately $150,000. To avoid suspicion and prevent others from copying him, Phillips claimed he was stocking up for Y2J! The next step was to peel off the stickers; this proved to be a grueling endeavor so he had another brainwave. He approached the local Salvation Army and asked for volunteers to peel off the stickers; Phillips promised to donate the pudding in return. Hilariously, he even earned an extra $800 at the end of the tax year because of his ‘charitable donation.’

Although he burned through his air miles (he and his family have traveled to over 40 countries), he currently has four million miles left because he keeps an eye out for frequent flyer incentive programs. In other words, he uses the cheap air miles to get free ones! The moral of the story: Major corporations make mistakes so keep your eyes peeled to take advantage of their stupidity.