From my experience, real cigar aficionados agree that many Dominican and Nicaraguan cigars are every bit as good as the best Cuban cigars. Cohibas, IMHO, are the most over-rated cigars made. For my tastes, a 1964 Padron is as good as any Cuban I've tried. Now, don't get me wrong, some excellent cigars are still rolled in Cuba but the real master blenders and rollers, along with the best, seeds left the Island over 50 years ago.
I've tried many of the cigar leaf pipe blends on the market - Russ's Stogie, GLP Key Largo and Robusto, C&D Habano Day Dreams and Billy Bud. Will try Old Dominion.
None taste like a cigar, smoke like a cigar, have the silky volume of a good cigar or the fragrance of a cigar. Hints, yes but nothing else. I had to learn to enjoy cigar blends for what they are - pipe tobaccos.
So, I would focus on a hearty, smooth, nicotine rich blends for your boss. Someone mentioned getting him a sampler. You could get him a GLP sampler. Can't go wrong. But maybe you can put together a best of class sample. An English, a Balkan, a VaPer, a Lakeland, and a cigar leaf. Make sure it includes some real flakes and maybe a plug, like GLP Jack Knife or Pirate Krumble Kake. The idea is to introduce him to the wonderful variety of pipe tobaccos. You can set him with a decent pipe and a dozen tins of tobacco for less than a box of moderately priced premium cigars.
Just my thought.
pax