1991: Sean Montgomery was a born hero. He was the result of an affair between Barbara Cudahy and ex-husband Travis Montgomery in an effort to create a viable bone marrow donor for leukemia stricken Molly Montgomery. After a successful operation, the Montgomery’s moved to Seattle, Washington.

2000: Matt lost his father when Travis to a sudden stroke. Though he had a chance to say goodbye to his father, Bianca did not. She was visiting her mother, Erica, in Pine Valley.

2006: Sean had grown up very independently. Barbara could not be bothered to raise her own children since Travis’ death. Sean ran away to Pine Valley to his uncle, Jackson Montgomery’s house. In Barbara’s absence, Jack became Sean’s guardian.
Sean was a troublemaker. He led on Colby Chandler and Sydney Harris. Things became heated at their shared Sweet 16 party. Sean slept with Colby. Distraught, Colby crashed Jack’s yacht into the harbor. Colby was presumed dead in the accident. It was Sean’s wakeup call to stop fooling around. Sean was relieved when Colby was found alive.
Sean’s sister, Bianca Montgomery, returned to Pine Valley. Bianca helped Sean realize he could not live the way he was living.

2007: Sean had a problem with monogamy, though he loved Colby. He slept with Ava Benton, his cousin Lily Montgomery’s half sister. Adam Chandler, Colby’s father, paid Ava to plant drugs on Sean. Jack was able to get Sean off on the charges, but his relationship with Colby became strained. Colby eventually moved out of Chandler Mansion. She moved in with Tad Martin and her stepmother Krystal Chandler. They were more open to Sean.
Barbara made a surprise appearance in Pine Valley. Barbara was trying to seduce Jack, which made Sean uncomfortable since her was married to Erica Kane, Bianca’s mother. Sean was especially fond of Erica. Bianca revealed Barbara had kept Sean and Molly away from her after she came out of the closet.
Sean caught Barbara with a video recorder she had planted in Erica’s yacht club room. Barbara wanted to expose Jack and Erica’s divorce to be a ruse. Before Barbara could review the tape, Sean took the recorder and threw it in the ocean. He implored his mother to leave town before she hurt anyone else.

2008: Sean and Colby befriended Dre Woods, a member of the garage band that practiced in the garage next to Tad’s house. They became concerned about Dre’s welfare when an investigator arrived at the house looking for them. Colby and Dre went into hiding in the Chandler tunnels. It turned out Dre was the runaway son of US Attorney Sam Woods.
Sean met Hannah Nichols while she was on the run for shooting Ryan Lavery. Hannah seduced Sean to be her alibi. They shared one night of passion at a motel. Sean had to admit to his infidelity to investigators, and Colby. Colby and Sean ended their relationship.
Sean moved back to Seattle to try and build a relationship with Barbara.