Dreaming of a bootlegger means planning for something secretive and needs to avoid discovery by others. It will be especially troublesome if your actions are caught and presented to the proper authorities such as the police department. If your actions are illegal, then it is not recommended to continue as your bootlegger dream is already indicating a fear of getting caught.
Bootleggers often sell alcohol for profit, and may be motivated by greed. In a dream, being a bootlegger may symbolize your own feelings of greed or your desire for financial gain. Overall, the presence of a bootlegger in a dream may suggest that you are feeling rebellious or defiant in your waking life, and may be seeking ways to challenge authority or the status quo. It may be a good idea to reflect on what is driving these feelings and consider healthier ways to express your desire for independence and autonomy.