In the 50s bougies would smoke cigars all the time, usually Cubans. Not only are they enjoyable but they're also part of a Bourgeois image.
Then comes Castro. Total commie chad that always has a cigar in his mouth. Dressed in fatigues to symbolize the ongoing struggle against imperialism and capitalism. His cigar has basically become an integral part of his image. American mayos start thinking about communism when they see cigars, especially around the time of the Cuban missile crisis. First came the ban on Cuban cigars, and then eventually less and less porkies were slonkin on stogies, usually switching to cigs and then eventually quitting in the 90s
Yeah, Castro himself actually stopped smoking cigars to promote anti smoking campaigns