Investing in cigars is just like investing in the stock market. If you can buy low and sell high, then go for it. I'm a capitalist by nature, so I say make a buck when you can. However, capitalism and philanthropy aren't mutually exclusive. I love giving away cigars (particularly if I have a bunch of the same cigar from a new batch, as it sounds like you do). There's nothing wrong with selling cigars to those who are fortunate enough to be able to afford them, and donating the rest to noobs/friends/those who are less fortunate.