American Airlines' Ultimate Travel Scam with Katie Boyle and Erin Jackson | 95

What happens when you give two men unlimited first-class flights for life? American Airlines found out the hard way when their "brilliant" cash-grab turned into a multi-million dollar nightmare, complete with impromptu Paris lunch dates, suspicious companion passes, and an airline determined to ground frequent flyers forever.

Katie Boyle (The Shift, I'll Do It Myself) and Erin Jackson (Grudgery, The Upshaws)join Misha for a first class conversation about American Airlines Airpass

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Fyre Fest goes up in flames, Madame Web is panned, the hot new crypto coin crashes. Who doesn’t love a good flop? From Silicon Valley scandals to Hollywood meltdowns - every epic fail has a story worth telling. Join TikTok superstar Misha Brown on Wondery’s The Big Flop as we unpack history’s most fascinating flops, frauds, and fiascos. Whether it’s Tom Cruise’s couch-jumping or Taylor Swift in Cats, we’re dissecting the moments when ambition, ego, and poor decisions collide. Each week, Misha and hilarious guests break down these spectacular crashes and try to answer the burning question: Who thought THIS was a good idea? Because on The Big Flop, the best stories are always about the worst ideas. New episodes come out every week.

Follow The Big Flop on the Wondery App or wherever you get your podcasts. Watch new episodes on YouTube, or listen to The Big Flop early and ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. New episodes every Monday.

• No. of episodes: 102
• Latest episode: 2025-07-14
• Comedy Society & Culture

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