Flags of our Grandfather's

What this episode covers

Deep Secrets is a new investigative comedy podcast about a family secret of Cold War proportions. A 12-episode narrative investigation, paired with six full-length video interviews featuring celebrity guests including Mayim Bialik, Ron Funches, Morgan Jay, and more. Comedian Hunter Hill and his sister Kaylan confront a life-changing family secret that was meant to stay buried. Season One begins with an accidental discovery that leads to a stunning revelation: their grandfather was secretly working for the CIA as part of what Smithsonian Magazine called a “real-life Ocean’s Eleven”—a covert operation that helped give rise to the phrase “can neither confirm nor deny.” Listeners will tune in because Deep Secrets offers the irresistible combination of a true family mystery, a Cold War spy thriller, and laugh-out-loud investigative storytelling. At its heart is a question anyone can relate to: How well do we really know the people who love us the most? Hunter and Kaylan invite listeners to discover the answers alongside them, as an ordinary childhood memory, a grandfather tending goats on a quiet farm, collides with the extraordinary revelation of a secret life inside the CIA. Every episode pulls back another layer of the mystery, blending genuine investigation, surprising historical revelations, and the messy, funny, deeply personal dynamics of siblings uncovering something their family was never supposed to know. It’s a story that keeps listeners asking, “How is this real?” and tuning in to find out what happened next. Uncover the secret mission the National Smithsonian calls "a real-life Ocean's Eleven."