Are Cuban cigars legal to possess in the United States?

The most common "penalty" for bringing Cuban cigars into the US is confiscation by US Customs.

In my 12 years of being in the cigar business, I have never heard of anyone being jailed for bringing Cuban cigars into the US. I have heard of individuals being jailed and prosecuted for trafficking in Cuban cigars (bringing large quantities into the US and reselling them).

Based on my experience and those of my customers, you have a 50/50 chance of having cigars confiscated by Customs when you re-enter the US.