While some purists say no, conventional wisdom says yes. When cigars are commingled, the rich scents and oils of the older and best cigars will marry with the younger ones, improving their bouquet. It might seem a trifle metaphysical and impractical, but the great cigars always throw off their aromas and oils into other cigars, as well as the cedar lining.
The older, drier cigars benefit from comingling as well, absorbing moisture from the younger smokes.
Purists, however, believe that keeping sticks separate preserves the signature aroma associated with each cigar. This belief is most prevalent with Habanos purists, but with the tobacco traveling that is prevalent today, (i.e., Dominican tobacco used in cigars from Honduras, Nicaraguan cigars containing Mexican tobacco, and—of course—Connecticut wrappers used worldwide) cigars today have less distinction than cigars in years past.