My Brother's Annual Visit

Good idea! You might also suggest FM Cellar or 1Q, if he doesn't like those then there's not much hope for him! Lol! Carter Hall is probably the best tobacco for anyone to learn pipe smoking with.

At first I thought maybe something with cigar leaf, since he's a cigar smoker, but I'll +1 pete03 on this - better to show what's unique about pipe tobacco, rather than how it's similar to a cigar.

better to show what's unique about pipe tobacco, rather than how it's similar to a cigar.

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Extremely well-said. I get Roth entirely but I know many avid cigar smokes that enjoy the pipe for more variety was well. I think the best approach would to simply be have him sample a few of your blends on hand and see if any take, rather than to buy anything special for him. The MM Legend is a great idea, they smoke so well, a total noobie could easily get a good smoke from one. There was a time when I just started myself that I swore against briars because any MM cob would out-smoke them, while I now prefer briar and know that is not the case, it's a great start! Who doesn't love a good cob time to time

I have been smoking rum twist rope lately, it has been tasting very similar to cigars to me for some reason. But you will probably be respondsible for prepping it for him. While the opposite of a light blend, it might be worth a try to get him to taste something that is similar to cigar and then break him into the other types of tobacco after that. I havent tested this idea on anyone. But I agree that CH usually tastes good and smokes easily so that is a good option as well.

I've been a cigar smoker for years. Being from Connecticut I always tended to gravitate towards cigars with a Ct. wrap, in the 7-12 dollar range,no matter where it was grown. That being said, my preferences are for a medium to mild stick. I am just beginning to sample the hundreds of pipe tobaccos, and so far I can't say anything I've tried is horrible. Including the pharmacy aros. Lately I have been sampling some English blends and today's TA was MacBaren's Burley London Blend. For my pallet I find it quite tasty without a lot of sugary casing. I also picked up some Erinmore Flake and I consider today to be a total winner. This is only my two cents for consideration. I'm sure you will find something worthy. Good luck.

Assuming your brother enjoys good cigars, I don't think he'd be all that impressed by the weak (Carter Hall) or the cloying (1Q).
And I really don't think a cob, with its soft, chewy bit and its stummel that protrudes into the bowl will win friends and influence people. A lot of guys like them because they're so cheap, sure. But they're not magic. They won't grant a rookie the smoking skills of a veteran.
If it was my brother, I'd clean and sterilize a good briar with a nice cake for his use while he's visiting. And if he ends up liking it, I'd tell him to keep it as a memento. Or he could leave it at the house for his exclusive use whenever he's in town.
But that's just me.

+1 Bigvan I agree on both counts. I like a corncob but it is usually used as a tobacco sampler not a full time pipe. Still prefer my briars for that. Also agree on the light flavoured tobaccos I cannot see a cigar smoker enjoying 1Q or Carter Hall. Both are smoked more for the people around you than the flavour of the smoke IMO. Rothnh idea about a tobacco that reminds him of cigar might be a good beginning or even an English with a sweeter casing. Early Morning Pipe? As a somewhat regular cigar smoker I can understand some peoples reluctance to smoke a pipe. There is also a stigma that pipes are for old men and a cigar is the mark of someone who has made it in the world. It's like guys drinking Scotch because their buddies do but really preferring rum and coke. I really think a pipe is something you have to have an infinity for to really enjoy it. You have to really enjoy the packing and lighting and ceremony of it all. If not it all becomes a big pain in the ass. I smoke my pipe on job sites because it is so convenient to put it away when the phone rings or when I climb a ladder and then when I'm done can take it out of my pocket or pouch and relight it again. If I let my cigar go out to cut a stair stringer or a batch of rafters I would never forgive myself yet sometimes a cigar hanging out of your mouth just doesn't always work.

Keep us posted Werdna on how your brother liked the pipe tobacco.

I'm a cigar smoker, as well as pipe smoker. I like CH, but when I returned from a long hiatus from pipes last year, the tobaccos that satisfied me were EMP and Peterson's Old Dublin. I really like CH, but I think that he's going to need more flavor if he's going to like a pipe. Compared to a good cigar, CH may seem bland and too light. A cigar leaf blend might also be a good choice - though I've not tried any and cannot recommend one. Just a guess, but if he says he tried a pipe and didn't like it, it's a good chance that he tried an OTC aromatic. Although 1Q is much better, IMHO, than most OTC aromatics, it may not be a good choice for a cigar smoker. He already likes tobacco, and is already used to the idea that good tobacco doesn't smell nice (to others), so no need to try to win him over with something that smells nice.