Dreaming about a shackled convict symbolizes your personal struggle and vigilance toward controlling the feelings of psychological and physical oppression. A life goal that is never accomplished.
A convict with chains around his feet on a chain gang in your dream implies a sense of control issues. Shackles can mean security and feeling protected by powerful authorities where there are fewer alternatives and little choices to be made since they hold all the resources.
Are you stuck in a situation or position that you desperately want to break free from? Or risk ruin if you stay for too long? It may be time pack things up and leave the past behind.