One of the most legendary miles and points feats was when Dave Phillips earned over a million American Airlines miles (and lifetime elite status) buying Healthy Choice pudding. Individual cups of pudding sold at the grocery store for 25 cents, and he filled up a van full across multiple grocery stores. Then he got one to bulk order 60 cases.
In total he bought 12,150 cups of pudding for $3,140, earning 1,215,000 miles. He donated the pudding to food banks (tax writeoff!) and they clipped the UPC codes for him.
He had to fill out each 500 mile certificate. The cost was still high, but miles were worth a lot more then. And his feat was memorialized by Adam Sandler in P.T. Anderson’s Punch Drunk Love.
That deal was honored. So was the 7 million AAdvantage miles I earned two years ago via SimplyMiles (making charitable donations to Mastercard’s charitable for sextuple miles). So was the US Airways holiday shopping promotion in 2009, buying stickers in a similar manner.
Pudding Guy was became one of the legends of FlyerTalk. Among this group I’d have to count:
Those members rose to prominence for things they did outside of the community. Phillips’ prominence was his mileage antics. As part of Punch Drunk Love he actually walked them through earning 1 million miles with LatinPass in the first half of 2000 by flying at least one international segment on each of the ten LatinPass member airlines, flying at least three segments on partner airlines (KLM, US Airways, TWA); staying at least three nights in at least two partner hotels and renting a car for at least five days from their car rental partners.
But not all of the greats are honored. Sometimes companies come up with a technicality. And sometimes these deals wind up in court.
One of the best attempts ever to leverage a company’s loyalty program offer happened 27 hours ago, and is going viral again in social media.
A 21-year-old biz student found a risk-free way to turn $700k into $23M.
Instead, he got embroiled in a lawsuit with a Fortune 500 company.
Here is the story that will make your blood boil: pic.twitter.com/ZxWB23skp3
— Jesse Pujji (@jspujji) December 12, 2023
Some of you have been around the points hobby long enough to remember
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Miles, Points, and Courtrooms: The Wildest Loyalty Program Exploits Revealed - View from the Wing
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