Molly Morgan is remembered as a strong and resolute convict woman. However, as this article discusses, her reputation has suffered at the hands of journalists and illustrators over the past 150 years. She has been depicted as a self-willed and resourceful woman, but also as a buxom mistress, or worse. Certainly, she was an exceptional and atypical character who defied the common stereotype by becoming a successful and powerful business woman. She was also, of course, a criminal, convicted numerous times for serious offences. But she has attracted many erroneous and, at times, eroticised representations which are not based on extant evidence and usually seem to ignore or deny her significance as a businesswoman and settler of the Maitland district. This article reflects on Molly Morgan's rich and often misrepresented life-story by considering these divergent depictions.