When Robert Caldwell walks into a room, your first impression is not that he is one of the leading cigar manufacturers in the country. First off, his height is quite intimidating. He is one of the few people I have ever met that I have to look up at to talk to. He is dressed impeccably, but more as a fashion designer then your run of the mill cigar guy. He has that strange Miami accent that for a while I mistook for some kind of European. Then, once you sit down with him and listen to him speak of his life and his work, it all suddenly starts to make sense.

This is a man who didn’t grow up on a tobacco field or from a third generation cigar family. This is a man who loved the industry and worked day and night to make his vision a reality. He grew up in the Miami scene and began to idolize cigar manufacturers like E.P. Carillo. In the 90s he became a huge fan of the La Gloria Cubana line, which in some way inspired him to become involved in the cigar industry.

 His first major venture was teaming up with famed Honduran legend Christian Eiroa on a project called Wynwood Cigars. It was inspired by the Wynwood Arts District of Miami, Roberts home turf. Eventfully the two manufacturers could not see eye to eye and amicably dissolved their partnership.

 It was then that Robert struck out on his own and created the Caldwell Cigar Company. He teamed up with the Ventura Cigar factory with one goal: to create unique blends using rare aged tobaccos. I think its safe to say he succeeded. His first lines, Eastern Standard, Long Live the King, and the King is Dead are now cigar store staples. His creative blending practices mixed with his creative and eye catching artwork has made Caldwell cigars one of the fastest rising companies in the industry.

 He has continued his success and has branched out to collaborating with other leading manufacturers. For the past two years, Robert has had the distinction of creating the two most anticipated cigars of the year. In 2016, it was his work with Drew Estate on the All Out Kings that had aficionados waiting like a kid on Christmas to try one. This year, he blew everyone away when he teamed up with Room 101 creator and dear friend Matt Booth to create the Hit and Run.

 He may not look the part, he may not act the part, and at first glance his cigars look more like a painting you would see at a very strange art museum, possibly on acid. However, you cant argue with his success, so make sure you try as many Caldwell Cigars as possible.


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