"The obvious fulfilling mob boss fantasy".... this has never come to my mind while I have smoked a cigar. I suppose I was never into the mob stuff. As well I have never pictured myself as someone else while smoking.
There is an added element of community with fellow cigar smokers. Some of the best conversations I have had in my life have been while smoking a cigar with others. You would be amazed how much can get accomplished in a conversation of gentlemen with different views, when everyone has something in common at that moment, such as enjoying a cigar.@seablue explained it well. It is just another experience to be enjoyed like eating fine foods, wine, bourbon, etc.
A cigar also slows down the mind of this non-stop fast past life. You are forced to relax, only puffing around once or twice per minute. It can be a soothing thing to the mind and soul. It has become my evening reward for a accomplished day, something to look forward too.
Very good!