In the end, he collected more than 12,000 pudding cups for a total of more than 1 million miles and gold status for life on American Airlines. His tale was even the inspiration for Adam Sandler's character in the 2002 film Punch-Drunk Love.
There may never again be another Pudding Guy, but we asked some of the top bloggers from our recent USA TODAY 10Best Readers' Choice Award for the Best Miles-and-Points-Blog about the craziest things they've done for miles, and they have indeed gone to extreme lengths. We're talking dumpster diving, sticker collecting and signing up for way too many credit cards. Here are the craziest things the top travel bloggers have done for miles.
Gary Leff, View from the Wing
Gary Leff rarely takes a day off from the miles game, even if that means "working" on Christmas. The points guru once spent Christmas morning at the Hilton Garden Inn Yakima buying stickers worth 140 US Airways points each through a promo. In all, he earned 16 million miles – a merry Christmas indeed.
Leff also relayed one of his favorite stories about the lengths people will go to earn miles. Back in 2005, there was a rash of dumpster divers scavenging through the half-eaten-burger-filled trash at Wendy’s in search of soda cups that could be exchanged for AirTrain credits, 64 of which were good for a free round-trip airline ticket.
Daraius Dubash, Million Mile Secrets
Daraius Dubash says that one of the craziest things he’s done for points is going for a baldness consultation with Bosley to earn Delta miles, which wouldn’t have been all that crazy if he had anything other than a full head of hair. Considering his complete lack of baldness, the consultation only took five minutes, but that didn’t stop him from receiving his Delta miles – or plenty of future mail offering him hair implants.
What do you do if Chase is offering Continental miles, but there are no Chase branches in your state? Drive to the closest Chase location, 200 miles away in the next state over. At least that’s what Dubash did when he drove from Lawrence, Kan. to Springfield, Mo. and back in one day – about 400 miles round trip, roughly the same as the measly number of miles he earned through the promo.
Daniel Eleff, Dan's Deals
What’s the craziest thing you’ve done for miles? Let Daniel Eleff count the ways.
In 2006, Eleff flew 14 flights in two days – all to and from Dallas – to earn more than 100,000 American Airlines miles and elite status. From 2008 to 2010, he checked into Hyatt Places hundreds of times during promotions that netted up to 13,500 United miles plus 6,000 Hyatt points plus a free night at any Hyatt in the world for every two stays.
From 2008 to 2011, Eleff used a credit card to buy hundreds of thousands of dollars worth of dollar coins from the U.S. mint at face value, then immediately deposited them into his bank account, spending no money but earning hundreds of thousands of points.
He’s also opened as many as 24 credit cards at a time, bought five figures worth of gift cards at a time and liquidated them into cash, and flown his whole family to Boston for a day to earn more than 300,000 JetBlue points through a promo. Oh, and yes, he was a Wendy’s dumpster diver, which earned him hundreds of free flights.
Was it all worth it? In total he’s earned more than 30 million miles.
Scott Grimmer, MileValue
In 2014, Scott Grimmer made a quick stop in Palm Springs to play in a tennis tournament just before heading abroad for five months. It just so happened that Cadillac and American Airlines launched a promotion to offer 10,000 miles for a test drive. While pressed for time, Grimmer is not one to pass up free miles, so he somehow managed to squeeze in an hour to test drive a car he knew he’d never buy, in a city he didn’t live in, just to get the miles.
Greg Davis-Kean, Frequent Miler
Most people go their whole lives without earning a million points and miles. In 2013, Davis-Kean thought it would be fun to earn a million in a month. “It turned out that it wasn't fun at all, but I succeeded,” he said. Half of the points came from signing up for 10 new credit cards in one day, and the rest came from using extreme-stacking techniques to buy stuff, earn miles on it, then sell it after.
