When Robert Caldwell established his cigar company in 2014, he made a name for himself with unusual tobaccos, unconventional artwork, and cigars that rarely looked or tasted quite like anything else on the shelf. His early releases, including The King Is Dead and Long Live the King, were produced in the Dominican Republic in collaboration with the Ventura family. But in 2015, Caldwell took a different direction with Blind Man's Bluff, a more accessible cigar manufactured at Agroindustrias Laepe in Danlí, Honduras, the same factory responsible for Camacho cigars. The original blend combined an Ecuadorian Habano wrapper with Honduran Criollo and Dominican San Vicente tobaccos. It was an attempt to reach a broader audience without entirely abandoning Caldwell's preference for unconventional blends. 

The Blind Man's Bluff Connecticut followed in March 2017, replacing the original Ecuadorian Habano wrapper with a lighter Ecuadorian Connecticut Shade leaf while leaving the binder and filler essentially unchanged. That distinction is important. Rather than creating a new cigar from the ground up, Caldwell used the same combination of Honduran and Dominican tobaccos to demonstrate how dramatically a wrapper can change the character of a blend. The Dominican component includes San Vicente, a hybrid tobacco developed in the Dominican Republic and prized for its distinctive aromatic qualities. Beneath the Connecticut wrapper, the heavier Honduran tobaccos remain, but their influence is softened by the creamier, more delicate character of the outer leaf. For a company known for making unusual cigars, Blind Man's Bluff Connecticut is a relatively straightforward experiment, and an interesting reminder that sometimes the most consequential change to a cigar is the one made on the outside.