Massimo went to college at North Western with Eric, Stephanie and Beth. He owns a shipping company that Eric suspects of having ties to underground crime networks. Massimo recently revealed to Eric that he has been a confidante to Stephanie for years - since Eric and Stephanie's first divorce. Under the influence of his feelings for Stephanie, Massimo collaborated to make arrangements for Brooke to leave and move to Paris. His interference caused animosity with Ridge. During Ridge's accident, hospital blood tests revealed that there was no possible way for Eric to be his biological father. Stephanie was stunned. Massimo reminded Stephanie of the time they were once together in college. Stephanie concluded that Massimo was Ridge's biological father. Stephanie asked that Massimo keep Ridge's paternity a secret. Massimo did as long as he could, although he always tried to pave the way for the man he could not admit was his son.

Once the truth was finally out, Massimo was overjoyed when the initially devastated Ridge soon opened his heart to his new father and left Forrester to join him. He was even more excited when he learned he had a second son, Dominick, from a long ago relationship with Jacqueline Payne. Things were just starting to come together for Massimo and his children when both his sons fell in love with Brooke Logan. When Brooke chose Nick over Ridge, Ridge turned his back on Massimo. Once Massimo learned that Jackie had known there was a chance that the baby Brooke was carrying could have been Ridge's (and as it turned out, was), Massimo was furious and blamed Jackie for Ridge turning his back. When he learned that Jackie had an affair, the strain was too much and Massimo had a devastating attack. Confined to a wheelchair and unable to speak, Massimo was forced to watch the manipulative Deacon Sharpe try to steal his wife right out from under him.

Massimo finally regained control of his life and after hiring Heather Engels to make sure Deacon fell back off the wagon, he and Jackie reconciled. It didn't last long, though, and they soon divorced. Massimo began getting closer to Stephanie again, even wondering if they could have a future together, and was instrumental in her finding the documentation that proved she was the rightful owner of Forrester creations. He was later thrilled when he got to meet Dominick, the son Felicia had given birth to nine months after leaving Los Angeles (and Nick) behind.