Actually, according to the language used in fines imposed by OFAC, it very may well be argued that it is indeed illegal.
"One individual was assessed a penalty totaling **** for allegedly dealing in property in which Cuba or a Cuban national had an interest"
If the roller is indeed a Cuban national AND is being paid to roll that cigar then the argument can certainly be made that the roller is a Cuban national that has interest in the cigars being rolled and purchased in the USA. (Regardless of the origin of the Tobacco.)
Not that I care if it is illegal or not. Just making the arguement that it indeed could be illegal. :wink: