fwiw, i have bought 'n brought and have had bought 'n brought for me cubans as follows....
me: i purchased a box in paris (once at a local cigar shop as even with the taxes, the dollar was still somewhat strong [remember those days?

]) and once duty free at cdg. in both cases, i just put the box between my clothes on my wheel-aboard. i cleared customs at ord (trip 1) and iad mid-field-ua (trip2) and never had a problem (as well as the 16 bottles of wine in my wheel-aboard on trip1 but i digress). just checked of nothing to declare-i guess i must look honest
the second time was when goalie-parents went to cuba a year and a half ago as part of an "educational group"

. they bought me a box and they didn't have a problem either when they cleared customs at mia.
also, fwiw, trip1 for me was pre-9/11 and trip2 as well as goalie-parents' trip to cuba was post-9/11