The cigar represents confidence, even defiance. From Churchill, to Guevara, to Castro. For Churchill and Castro, the cigar represented confidence and defiance during a time of immense national crisis. Despite giving up cigars in the 1980s, the association is so powerful that Castro is still firmly associated with the product.
The cigar is a symbol of success. Partly this is down to the product’s generally pricey nature. No rendition of a “fat cat” businessman is complete without a large cigar.
The cigar commands respect, but can also be ridiculous: see Groucho Marx.
But a cigar also represents relaxation. A good cigar takes at least 30 minutes to smoke. If you light a cigar, you generally need to sit down. The product instructs observers that “this is me time”. Jay-Z has spoken about cigars being a kind of self-reward.
As with most premium products, the heritage, provenance and craftsmanship elements also all come into play.