What if you stick with the cigar theme? You could create compartments in the box to hold things like a cigar cutter, lighter, and a few special cigars.
I agree with this. I have a collection of cigar boxes that I use to make all sorts of decretive storage boxes. I do this by papering them with hand made paper. This of course is not that manly. You could get a guy color like grey or hunter green. Paper the whole thing with it and mod podge. Then paper the top with a contrasting color (manly) making the top layer smaller to leave an 1/2 inch frame around the surface. Then in side the inner rectangle you can mod podge news paper clippings from the sports page. Using teams or sports that you know he likes. For my son I would do vikings football articles and horse racing. The you can accent this by mod podging cigar belts (the little brand name belt that is usually wrapped around new cigars) in between or even over lapping the news paper clippings. You can do this on all 4 sides of the out side and all for sides of the inside. Then when it is all dry you can build the compartments like mentioned by vibrant notions. Good luck i would love to hear about what you did.