I blame Clinton.
Not always. Well… one is a politican but I don’t think of him as a fat-cat politican.
Reno. You could shoot a man, just to watch him die.
Way back when, political and/or big business decisions were made by a select group of men meeting in “smoke-filled rooms.” The smoke in question arose from cigars which, as has been noted, were luxury items. Many of the decisions made in those smoke filled rooms were beneficial to the cigar smokers in those rooms and of dubious worth to the common man. Cigar smoking came to be associated with those rich and powerful men who met in secret; plus, cigars combined with dollar signs ($) were easy to include in political cartoons. Those cartoons were probably the root cause of cigars being associated with dubious characters. IMHO, YMMV.
Well, for that, you’d need lawyers, guns and money – but a cigar would be nice, too.
OK, so let’s say that smoking a big ol’ Havana predates Castro. What was in Cuba before his takeover? Casinos. Money. Mob money.