For decades, drivers on I-95 have been bombarded by nearly 200 garish billboard signs advertising South of the Border, a roadside attraction straddling the North and South Carolina state line. We dive into the story of Pedro and his sombrero-shaped empire—from its Jim Crow era origins to becoming the most legally challenged sign system in America, sparking debates about free speech, cultural appropriation, and what happens when one man's kitsch becomes a constitutional battlefield.