The buildup of tar, moisture and nicotine can heavily affect a cigar's flavor. Tobacco is like a natural filter. With every puff you take, certain properties of the cigar are captured in the tobacco. As the moisture builds up, the intact flavors are heightened toward the end of the smoke.
The way you cut a cigar can increase or decrease the concentration of flavor towards the end. A narrow opening at the head of the cigar, caused by a punch or wedge cut, acts as a collecting point for the tar and moisture. A broad opening, cut, for example, by a scissors or guillotine, will decrease the flavor buildup.