Dipping a cigar in whiskey is generally not recommended, as it can negatively affect the flavor and burn of the cigar. The moisture from the whiskey can cause the cigar to burn unevenly and can also cause the flavors to become muddled. Additionally, the added moisture can also create a harsh and bitter taste.
If you enjoy pairing cigars with whiskey, it's recommended to sip the whiskey between draws of the cigar rather than dipping the cigar in the whiskey. This allows you to enjoy the flavors of both the cigar and the whiskey separately and also helps to prevent any negative effects on the cigar's flavor and burn.