Episode Details

In 1920s Miami, a man named Philip D. Cupp ran a thriving hot-air-balloon business, lifting tourists over the ocean for postcard views. By 1925, disappearances along the coast reportedly spiked, and witnesses told police they’d seen a man fall from a balloon. When questioned, Cupp said he hadn’t flown that day—he pointed to “another company.” The problem: locals knew he was the only balloon operator around.

Investigators set a sting. An undercover officer—Joffrey—booked a solo sunrise flight. For a while, there was only water, burner hiss, and wind. Then Cupp leaned close and said, “What goes up must go down.” From the beach, binoculars tracked a violent sway. The basket pitched. The balloon plunged. Both men were lost.

The legend that followed claims Cupp was responsible for 400+ disappearances—a number that may reflect folklore inflation more than court-clean counts. This episode critiques the record versus the retelling: how a hospitality business becomes a hunting ground, how alibis evaporate at altitude, and why some numbers stick even when the balloon is gone.