it was a few years ago, from a local cigar shop. It was a normal business transaction, and the cigars were supposedly "pre-Revolution". Never got any threatening calls from the Treasury police, although I think I did pay in cash so it was a relatively anonymous sale. Theoretically a good humidor will keep Cuban tobacco in suspended animation for 50 years. Never was a regular customer there, the owner was somewhat of a reactionary.
BTW I am aware of OFAC regulations, and I have visited Havana twice in the last 5 years. It is not illegal to travel to Cuba. It is illegal for US citizens to spend money in Cuba, without an OFAC license, and that will only be known by OFAC if you state in writing or make oral statements which comes to the knowledge of an interested government official.
I still maintain that possession of Cuban tobacco is not illegal, not anymore illegal than it is to physically travel to Cuba.
So yes, any verified financial transactions that occur which directly benefits the Republic of Cuba, post-1959 Revolution, yes, OFAC will handle the niceties, and yes, Cuban cigars are routinely confiscated at gateway airports from US travelers, and yes, threatening letters are randomly sent out to persons OFAC suspects of having purchased Cuban tobacco, but so far I've heard of no actual fines or prison being given to US citizens for possession of post-1959 Cuban tobacco.
The law and the enforcement of the law are two different things. For example, in April, 2001, when Pres. Clinton shopped at Cigar House in Terminal 3 of Heathrow and made a well-publicized purchase of a Cuban cigar, Clinton bought a Bolivar Lonsdale, and paid £7.84 ($11.40) for the smoke. Years after the fact, OFAC has apparently never bothered to send him a request for information about the purchase nor has Clinton ever been sent a notification of an investigation into the purchase of the cigar.
Tobacco(regardless of origin) is not a controlled or illegal drug, so possession of (Cuban) tobacco is not illegal. Commercial sale of post-1959 Cuban tobacco is a different matter entirely.
The current law says that you can not import them, but in the US, you can possess them. Chances of getting caught: miniscule. Rumor has it that the custom agents destroy them by burning them one by one - very slowly!
In the US, you can legally purchase Cuban cigars here (Pennsylvania location): <
http://www.famous-smoke.com/>