We could make recommendations all day long but your best bet might just be to e-mail a rep, such as Time Blythe (tblythe@cigar.com). Don't worry about them trying to sell you what's best for them rather than you and your mentor, they'll come up with something great. Tell 'em the forum sent ya.
See there's a GREAT suggestion that wouldn't have cracked the first 50 to enter my head, but would probably blow all 50 away. Gotta love The Beard. For size, the standard cigar would be the grand master, and it'll match the tubo sampler which may or may not be a plus, depending if you want to give him variety. However, a lot of guys that are really into cigars like the smaller ring gauges (width, basically), which would be the Low Rider. The Chubby (if you can get past the double-entendre of handing the guy a tin of chubbies) would offer the most complexity because of the continually changing ring gauge due to what we call a perfecto shape (tapered at both ends). Some guys love torpedoes (the Stout) though (they can chance how the smoke hits the pallet and make for a fairly fool-proof cut), and though this one will probably have the longest smoke time because of the length of it, if you know he tends towards smokes with tapered ends like this, it's the one to choose.
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