In Episode 13 of the Southern Blueprint Podcast, we begin a two-part series exploring the true story of the Gentleman Smugglers and the massive federal investigation known as Operation Jackpot. This is a deeply Southern story—rooted in the Lowcountry, stretching from South Carolina’s barrier islands to the Caribbean, and ending with one of the most significant maritime drug busts in U.S. history.

This episode focuses on how it all started.

The Rise of the Gentleman Smugglers

The men at the center of Operation Jackpot did not see themselves as criminals in the traditional sense. Many were experienced sailors, businessmen, or thrill-seekers who believed they had cracked the code: move marijuana by sailboat, blend in with legitimate coastal traffic, and avoid the attention that speedboats and violence attracted.

Using established maritime routes, they ran cargo through places like McClellanville and Hilton Head, funneling drugs inland through South Carolina hubs such as Columbia. For years, the system worked. The money was good. The risks felt manageable. And the smugglers grew increasingly confident.

This episode examines how those routes functioned, how the network expanded, and why success ultimately became its greatest weakness.

A Southern Coast Under Watch

As the scale of the operation grew, so did law enforcement scrutiny. Federal agencies began piecing together patterns that stretched across state and international lines. What had once appeared to be isolated incidents were suddenly part of a much larger picture.

A key figure in the government’s response was Henry McMaster, then a young U.S. Attorney in South Carolina. Operation Jackpot would become one of the most ambitious drug investigations of its era, targeting an operation that relied on geography, patience, and the assumption that it would never attract sustained federal attention.

Part 1 of High Tide, High Times is about context and momentum. It introduces the characters, the coastal routes, and the mindset that allowed the Gentleman Smugglers to thrive. It also highlights the early mistakes and pressures that signaled the beginning of the end.

Part 2 will follow the collapse—indictments, international escapes, fugitives, and the full force of Operation Jackpot bearing down on the Lowcountry.

For listeners who want to go deeper, extended notes, companion content, and behind-the-scenes context for episodes like this are available through The Hidden Pine Lodge on Patreon. Members also get access to our private Discord, where the Southern Blueprint book club lives, along with ongoing discussions around Southern history, folklore, and the stories that don’t always make it into the main feed.