The $33 Million Pepsi Challenge: Marketing's Most Audacious Loophole

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In 1996, a 21-year-old business student named John Leonard walked into federal court with the most audacious marketing claim in history:

Pepsi owes me a military-grade Harrier Jet, and I can prove it.

John is my personal marketing hero, not because he won (spoiler: he didn't), but because he saw what no one else did - a literal interpretation of Pepsi's flashy "Pepsi Stuff" points campaign.

The commercial showed a teen flying to school in a Harrier jet with the simple caption: "7,000,000 Pepsi Points."

Where everyone else saw obvious hyperbole, John saw a binding offer. He did the math: the fine print allowed sending in 15 cents per point instead of buying Pepsi. So for about $700,000, he could get a $33 million military aircraft. This man wasn't just thinking outside the box – he was ready to fly it to school.

Leonard rounded up investors, collected his 7 million points, wrote a check for $700,008.50, and submitted his order form requesting the jet.

Pepsi's response? "Ha ha, good one."
Leonard's response? See you in court.

Judge Kimba Wood eventually ruled for Pepsi, stating that "no reasonable person would have understood the commercial to be offering a Harrier Jet." The court determined the ad was obviously puffery, not a legitimate offer.

What might this look like in 2025?

In today's meme-economy, I can't help but wonder what would happen if this played out on TikTok or Twitter.

Some brand would absolutely lean in and send the guy a toy jet or create a limited edition "Lawsuit Flavor" Pepsi.

The missed opportunity here was epic. Imagine if Pepsi had pivoted and offered Leonard a "Civilian Pepsi Air Force" role as brand ambassador? Or launched a mini working drone version of the jet as a limited-edition prize? In a world where brands like Wendy's built entire personalities on sassy comebacks, the lawsuit could have been marketing gold.

Instead of court, this would be settled in the comments section today, with the brand's response going viral instead of getting buried in legal briefs. The best modern brands know when to say "you got us" and turn a potential PR disaster into engagement gold.

You can pretty much heck off exactly how this would unfold.
Within hours, competing brands would jump in with their own takes.

• Red Bull would offer him "wings instead of jets."

• The U.S. Air Force recruiting account would post "We have jets if you're interested."

• Every meme account would generate endless variations of "me trying to cash in my points for military equipment."

The original claimant would hit a million followers overnight. Podcast invites would flood in. A crowdfunding campaign to "Help John Get His Jet" would probably raise more than the original $700K. Late-night hosts would do jet-themed monologues for a week straight.

The genius move would be Pepsi embracing the chaos: "Fine, we'll give you a jet experience."

They could partner with a flight simulator company for a "7 Million Points Experience," or create an actual sweepstakes where one lucky customer gets a fighter jet ride-along with a retired pilot. The whole thing would cost a fraction of their annual marketing budget but generate 10x the brand awareness.

And let's be honest – some marketing director would get a promotion for "creative crisis management" rather than a termination letter for the original mistake. That's the difference between 1996 and now – what was once a PR nightmare is now engagement currency in the attention economy.

My favourite part of all this? The Simpsons predicted this reality. Two years before this incident, in a 1994 episode titled "Bart Gets an Elephant," Bart wins a radio contest where the joke prize of a full-grown elephant turns out to be real, forcing the station to deliver.

Just another case of “The Simpson’s did it first”

So here's to John Leonard, the man who took hyperbole literally and almost walked away with a fighter jet. In content marketing, we call that "testing the boundaries of your offer."

Just make sure your terms and conditions exclude military hardware.

✌️ Tim "Jet Fuel Can't Melt Pepsi Dreams" Hanson
CMO @Penfriend.ai

P.S. Do you think he should have got the plane? Is is even legal for a civilian to own a fighter jet?

P.P.S. I just found out Netflix did a who docuseries on this. I know what I’m watching this Sunday afternoon.