Rosalind was born in Liberty City where she lived with her mom, Candice Venters. The pair lived in Hepburn Heights, a small district filled with housing projects that is located in the Portland borough. Rosalind also had an older half-brother named Vincent, who didn't live with the pair, but often stopped by when he wasn't on a job to check in on her. Candice was often not around, usually out partying into the early hours of the morning and then spending the following day sleeping off the various drugs and alcohol she had consumed. As a result, Roz became pretty self-sufficient, teaching herself various skills to get her through her day to day life. Vincent did his best when he was able to come around, but his job had him away for days, weeks, and even months at a time. But Roz loved him dearly, and while she grew to resent her mother, she greatly looked forward to when her brother came around and would take her with him to his friends garage and teach her various things about cars.

When Rosalind was 13, Vincent came to both her and her mother and offered to move them to Vice City for a fresh start, telling them he had a great opportunity there and could provide for them much better. Her mother, never one to turn down free anything decided to pack up what little they had and move them down with him. Rosalind hated Vice City and how sunny and open it felt compared to Liberty City, however she did grow to love one thing... a nearby garage that often let her hang around, even paying her to do odd jobs here and there. It didn't take long for Charlie Nakamura, the owner of the garage to pick up some useful talents Rosalind brought with her. She was small but quick, and good at going unnoticed, and she unwittingly had picked up some useful information on the few times he had her running errands and deliveries for him. He started utilizing her for more jobs related to gathering information, in return he taught her to drive, and let her hang around the shop, going as far as to turn one of the unused storage rooms above the garage into a room for her to use when she did not wish to deal with her drunken mother. He also started to teach her how to utilize her artistic talent for designing liveries for cars.

When Rosalind was 15, her brother Vincent went missing. Having been use to him being going for days to months at a time, Rosalind did not think much of it first, until some people that worked with Vincent came by to ask for him. Finally, one his bosses, a man named Rosario Martinelli came to visit Rosalind and her mother to express his worry and condolences. Rosalind did not like him much, but her mother latched on to the man right away, playing up the worried mother act to a tee. This would be the start of Rosario and Candice's relationship much to Rosalind's dismay, and by the time she was 16, the two had gotten married and she was moved to his estate on Starfish Island. The only good thing that came from this was Rosario's daughter, Portia. While the two didn't initially get along, Rosalind soon discovered that Portia (Or Poppy as she lovingly started calling her) was just as trapped with a terrible family as she was. She soon took it upon herself to try and take care of Poppy just as her brother Vincent had often taken care of her. Unfortunately she was kicked out of the estate and family about 8 months after moving in, but she did her best to take care of Poppy from afar, and started working on plans for getting her out of the tightly guarded and monitored estate.

Over the next 9 years, Rosalind would continue working at the garage with Charlie Nakamura, and eventually became involved in the underground racing scene in Vice City through him. While she didn't race a lot herself, she was known for her livery designs in the community and was often found working on various racers cars in her downtime. She also continued work as an information gatherer for Charlie, and made many connections over her years in Vice City.

Roz currently designs the advertisements and logos for the various business ventures of members of the Black Lotus Motorcycle Club which she is apart of. She mostly keeps to herself, usually working on her tablet in the corner of the yard.