Macanudo's roots reach to Jamaica during World War II, when the island's cigar industry expanded for the British market. The name—an expression meaning “fantastic”—was chosen after King Edward encountered the word through Argentine polo players. In the mid-1960s, tobacco veteran Edgar Cullman developed the modern Macanudo around the upper primings of Connecticut Shade tobacco, proving that the leaf could anchor a premium cigar.

Macanudo Café became an American icon for its smooth, consistent character. The company also pioneered long-term vintage-tobacco work, releasing a 1989 Vintage Cabinet Selection made with ten-year-old leaf. Production moved to Santiago, Dominican Republic, in 2000, and the portfolio has since expanded through Gold Label, Inspirado, M, and Emissary while retaining the careful construction and accessible balance that made Café a classic.