Roman and Diana became involved in another adventure when Roman began investigating a mob family known as the Torreses. Several attempts were made on Diana’s life during this time until the Torres family was finally brought down. Soon afterward, Roman and Diana were led to a trap by Stefano DiMera and became his prisoners in his underground compound. During this time, he taunted Roman by suggesting that Marlena was still alive.
After concluding that Marlena was really dead, he proposed to Diana. Just as they were in the middle of their ceremony, a man named Cal Winters arrived and claimed to be Diana’s husband. During an argument between the two men one night at the Brady house, Roman was shot in the neck. Under hypnosis, Diana remembered accidentally shooting Roman. She was so overwhelmed with guilt that she left town.
In 1990, Roman met Isabella Toscano while trying to exonerate Kayla Johnson for the murder of Marina Toscano. It was eventually revealed that Isabella had accidentally killed her sister and blocked out the entire ordeal. While trying to help her regain her memory and clear Kayla, he developed strong feelings for Isabella. It was soon revealed that Isabella was actually the biological daughter of Victor Kiriakis.
Roman and Isabella broke up after their Cruise of Deception adventure, but eventually reconciled and even became engaged after he solved Nick Corelli’s murder. One night, Roman was drawn to the pier and was astonished to discover his presumed dead wife Marlena. The two shared an emotionally touching reunion. Marlena had been in a coma on a Caribbean island for the past five years. Roman broke the news to Isabella and she broke things off with him.
Roman and Marlena decided to investigate her missing years. Their search led them to the island of San Cristobal, where they discovered another Roman Brady! This one looked like Roman before plastic surgery. DNA tests confirmed that the “old” Roman was the one and only, who had escaped his jungle prison. John realized he was free to love Isabella again, who was pregnant with his child.
In early January 1992, John began having flashbacks about a woman and kept this a secret from Isabella. It turns out that John previously was involved with a woman named Danielle Stevens, a jewel thief. All clues to a mysterious locket led to the Alamains. After barging in on Lawrence and Carrie’s romantic evening, John pulled out a gun on Lawrence. Lawrence revealed, though, that John was his younger brother Forrest Alamain who presumably drowned in a pool at the age of three. John wanted nothing to do with the Alamains.
John and Isabella married in May of 1992, but the wedding wasn’t without it’s complications. As Isabella walked down the aisle, she began experiencing contractions. She gave birth to their son Brady Black in another room at the church, then happily made their union legal.
With Victor’s help, John took back his rightful Alamain inheritance. He also used his money to donate to charity and finance the Brady Fish Market, making it the Brady Pub. John also gave Isabella a dream honeymoon in Venice Italy. Their happiness was doomed when Isabella was diagnosed with inoperable pancreatic cancer. She wished to return to Italy her final days and sadly died in John’s arms.
The only person who could get through to a grieving John during this time was Marlena. John soon discovered Marlena trapped inside a pit in a condemned warehouse, orchestrated by Stella Lombard. They thought they were going to die and reminisced on their past love. Roman arrived just in time and rescued them. John began dating Rebecca Morrison in an attempt to forget about Marlena.
In February of 1993, John decided to head back to Italy. Marlena tracked him down on the Alamain jet. The two gave into their feelings and made love. A guilty Marlena returned home, where Roman had planned a surprise anniversary party for her. One night at a Titan Publishing party, John and Marlena once again gave into their feelings and made love on a Titan conference table. Little did they know that Marlena’s teenage daughter Sami caught them in the act. This moment of indiscretion would later result in daughter Belle. Marlena soon discovered she was pregnant, but blood tests proved that the baby was Roman’s.
In the meantime, John was introduced to one of the Horton Center social workers, Kristen Blake. Alice Horton did some matchmaking and they each ended up at the Horton cabin, where they made love in the shower. John would soon break things off with Kristen after he discovered that she was Stefano’s adoptive daughter and engaged to Tony DiMera. Soon afterwards, Kristen helped deliver Marlena’s baby. Roman and Marlena decided to name the baby girl Isabella in honor of John’s late wife. Marlena eventually confessed her affair with John to Roman, and it was eventually revealed that John was Belle’s biological father.
John attempted to stop Kristen’s wedding to Tony when he claimed that he had evidence linking Stefano to the murder of Curtis Reed. Stefano fled the church and drove off in his car. John believed that Stefano was trying to flee Salem in order to avoid murder charges, so John shot at the car tires. Stefano planned it so that his car exploded and went off a road. Kristen accused John of murdering her father and married Tony in February of 1994. Tony learned that Stefano was indeed alive, but kept it a secret from Kristen.
Stefano would soon begin sending puzzle pieces to John of an estate. After being put under hypnosis by Marlena, John retreated to Maison Blanche in New Orleans, 1994. He was shocked to discover a drugged Kristen upstairs and a gun-toting Stefano, who had faked his death (again). Celeste knocked John out and he woke up to discover himself locked inside a cell in the basement. He soon realized that this is the place where he became “The Pawn.” Stefano tortured John by forcing him to watch Tony and Kristen making love. John managed to escape and tie Stefano up, but released Stefano when he discovered that Marlena had been taken hostage. Roman had arrived in the nick of time to save John and Marlena from being poisoned with gas.
