Caldwell Cigar Co. was created in 2014 by founder Robert Caldwell, but his journey in the cigar world began much earlier. Robert, always a businessman, jumped into the biz' distributing cigars and cigar accessories to high-end hotels and restaurants. In 2012, Robert Caldwell and Christian Eiroa collaborated to create the Wynwood brand, made at the artistically focused Wynwood Factory in Miami. A short period later, Robert transitioned and Caldwell Cigar Company was born. Produced at Tabacalera William Ventura in the Dominican Republic, Caldwell cigars are characterized by their atypical branding and marketing and their refined, Dominican-inspired smoking profiles.

Robert Caldwell's love of modern art bleeds through in the artwork displayed on every project; Robert has said he has his hands on every aspect of the design process. This is evident with the striking branding of Caldwell cigars such as Eastern Standard, Long Live the King, and Anastasia. Caldwell Cigar Co. is also known for using aged and rare tobacco vintages in their blends. Caldwell has had various partnerships and distribution relationships with different brands and factories in both Nicaragua and the Dominican Republic; these collaborations include the likes of Drew Estate, A.J. Fernández, Camacho, and Room101. Robert Caldwell has never been afraid to change the status quo to create a unique project, and Caldwell Cigar Company has provided the perfect outlet for such innovation.