What happens when you don’t take the win?

This episode of The Shallow End delivers two unforgettable stories about poor decisions, improbable survival, and the fine art of knowing when to walk away.

First, a Texas man is released from jail, handed his belongings, and given the one instruction that matters most: leave. Instead, he realizes something is missing—his confiscated marijuana—and makes the baffling choice to climb back over the jail fence to retrieve it. The result? No weed, more charges, and an instant promotion to the Shallow End Hall of Fame. A perfect lesson in why some exits should never be re-entered .

Then, the episode pivots from modern misjudgment to 19th-century audacity with the astonishing true story of Professor Thaddeus Lowe, a self-taught scientist who accidentally drifted by hot air balloon behind Confederate lines at the dawn of the Civil War. Shot at, nearly arrested, and mistaken for a demonic flying contraption, Lowe somehow talked his way out—then turned the entire ordeal into a meeting with Abraham Lincoln and the creation of America’s first military balloon reconnaissance program .

Along the way, listeners are treated to a jaw-dropping listener story involving gasoline, a bonfire, a Kiss music video, and the Milwaukee River—plus a reminder that eyebrows do, in fact, grow back.

Equal parts absurd, historical, and painfully relatable, this episode explores those fragile moments when the universe says, you’re done here—and what happens when someone ignores it.

Life lessons included. Jail fences should not be climbed. Fire tricks should not be attempted. And when freedom hands you the door… take it.

Learn more about your ad choices. Visit megaphone.fm/adchoices