Most people walk past grocery store promotions without a second thought. David Phillips was not most people. In the spring of 1999, this sharp-minded civil engineer stumbled upon a deal so absurdly good that it would earn him international fame, a lifetime of free flights, and a nickname he would never shake.
All it took was $3,140 and more chocolate-fudge pudding than any one family could ever reasonably consume.
An Engineer Spots an Opportunity
It was a routine grocery run in May 1999 when everything changed. Phillips, who worked as a civil engineer at the University of California at Davis, was pushing his cart through the frozen food section when something on a Healthy Choice entrée package caught his attention.
The brand was running a promotional campaign with several airlines — purchase ten qualifying Healthy Choice products, and receive 500 frequent flyer miles. Better yet, anyone who submitted their proof of purchase before the June 1999 cutoff would receive double the reward: 1,000 miles for every ten items.
Phillips started tossing frozen dinners into his cart at roughly $2 apiece. Then he noticed that Healthy Choice soups also qualified, and those ran about 90 cents per can. But the truly staggering find came at a discount grocery chain called Grocery Outlet.
Sitting on the shelves were individual cups of Healthy Choice chocolate-fudge pudding, priced at just 25 cents each. Every single cup had its own UPC barcode, which meant each one counted as a separate qualifying product. Ten cups for $2.50 would deliver 1,000 airline miles under the bonus deadline. The math was almost too good to be true.
Running the Numbers
Phillips did what any self-respecting engineer would do — he went home and built a spreadsheet. He told Time magazine that his engineering instincts kicked in immediately, and he mapped out the cost per mile for every qualifying product he could find.
Frozen dinners yielded miles at roughly 20 cents each. Soup brought that figure down considerably. But pudding obliterated everything else on the list. At a quarter per cup, he could acquire miles for a fraction of a penny apiece.
None of this was happening in a vacuum, either. Airlines had been selling miles in bulk to credit card companies, hotel chains, and car rental agencies for years, typically at just a couple of cents per mile.
That meant the promotional partner — in this case ConAgra, the parent company behind Healthy Choice — was buying miles for far less than the price of an actual plane ticket. The publicity alone was likely worth the cost to ConAgra, and the airlines were selling a product that often went unredeemed anyway.
Phillips and his wife Cindy, a schoolteacher, had been slowly accumulating frequent flyer miles for five years with dreams of a European vacation. He realized that this pudding promotion could not only get his two young daughters seats on that trip, but could bankroll years of additional travel. The decision was that he would buy every cup of pudding he could get his hands on.
Clearing the Shelves Across Sacramento
Over the following days, Phillips swept through ten different Grocery Outlet locations scattered across the Sacramento area, emptying every last cup of Healthy Choice pudding from their shelves.
When his local store ran out of stock entirely, he convinced the owner of the Woodland Grocery Outlet to place a special order directly from the distributor. Two full pallets of pudding arrived shortly after. When people asked why he was buying such absurd quantities, he casually blamed Y2K preparation.
By the time his purchasing spree ended, Phillips had acquired 12,150 individual servings of chocolate-fudge pudding at a total cost of $3,140. His garage became a warehouse, with cases stacked from floor to ceiling.
He began sharing the details of his scheme on a website called Webflyer, a popular forum among frequent flyer enthusiasts, posting under the handle “Pudding Guy.” Fellow members were deeply skeptical at first, but the photographs of his pudding fortress quickly silenced the doubters.
From Barcodes to Boarding Passes
Now Phillips faced a different kind of challenge. The bonus deadline was closing in fast, and someone had to physically peel the barcode label off every single one of those 12,150 pudding cups.
He and Cindy dove into the task themselves, but the sheer volume was punishing — Cindy developed blisters on her hands from the repetitive peeling. Desperate for help, Phillips hauled the remaining pudding to two local food banks and the Sacramento Salvation Army.
The charitable organizations struck a deal: they would strip the barcodes in exchange for keeping all the pudding. Larry Hostetler, the community relations director for the Sacramento Salvation Army, remarked that they had never encountered anything quite like it.
Phillips got every barcode into the mail before the cutoff. Weeks later, a towering stack of 500-mile certificates arrived at his door, totaling 1,253,000 frequent flyer miles. He spread a portion across accounts with United, Delta, and Northwest airlines, but funneled the bulk — well over a million miles — into his American Airlines AAdvantage account.
That volume was enough to earn him lifetime Gold status and priority boarding on every future American Airlines flight.
The charitable donation of all that pudding came with one final perk. Because Phillips had given away the vast majority of his purchase, he was able to claim $815 in tax deductions, shaving his effective cost down even further.
When all was said and done, his 1,253,000 miles translated to roughly 50 roundtrip flights anywhere within the United States, 21 roundtrip journeys to Australia, or 31 roundtrip tickets to Europe — all from pudding cups that cost less than a pack of gum.
A Legacy Built on Pudding
The story did not stay quiet for long. Reporters from The Wall Street Journal and The Times of London came calling, and Phillips landed a segment on NBC’s Today show. His unlikely tale of pudding-fueled travel even made its way to Hollywood, inspiring a subplot in the 2002 Adam Sandler film Punch-Drunk Love.
Phillips had no intention of slowing down. Within a year, he discovered another path to a million miles through a promotion called the Latin Pass, which required flying ten different Latin American airlines within six months.
Phillips knocked it out in just two trips over ten days. He later told HuffPost that nothing beats taking the time to truly understand how mileage programs work.
By 2011, Phillips had visited 40 countries and accumulated more than six million frequent flyer miles in total. His daughters Katie and Emma, who were just seven and five when Dateline UC Davis first covered the pudding story in 2000, grew up as experienced global travelers.
Katie eventually flew solo to Italy, while Emma used miles to visit friends on the East Coast on multiple occasions. Phillips told UC Davis Dateline in 2011 that worthwhile deals exist everywhere for those willing to seek them out.
Phillips eventually rose to the role of associate vice president of energy and sustainability at the University of California.