Oddly enough, you might have more problem sending the jerky than the cigar, Arky. The CBSA (Canadian Border Services Agency) is pretty strict about unknown plant or animal product entering the country lest a hidden pathogen get into the food system here. Homemade jerky may well get confiscated at the border.
The cigar, on the other hand, is a packaged and inspected commercial product. It may be inspected to make sure it's not harboring any pests, but otherwise it should come through the border just fine. It's possible that your buddy might be assessed duty and taxes on it, but it's equally likely that CBSA will let it through without fees.
This is the great game for Canadian pipe smokers wishing to take advantage of much lower tobacco prices in the USA. Every tin we order from SP, 4Noggins, etc is subject to duty and import taxes. Sometimes you get hit and sometimes not, but recently, it's been every order for me, so my cellar is in a holding pattern until my next trip south of the border when I can bring a few tins home personally.