In 2014, in order to gain leverage with the King of Hell Crowley, the Knight of Hell Abaddon abducted Crowley's son Gavin MacLeod from 1723 before he could board The Star to sail to America. Following Abaddon's death, Crowley refused to allow Gavin to be returned to his own time, knowing that he would die when The Star sank off the coast of Andover, Massachusetts.
As a result of Gavin's disappearance, he was not present when his fiancé Fiona Duncan arrived looking for him. Thinking that Gavin had attempted to leave her behind, Fiona boarded The Star as a stowaway where she was without Gavin's protection. When she was found and without Gavin to protect her, Fiona was brutalized by the crew and passengers. Though her teacher Mistress Aloway was aboard, she encouraged the brutality instead of protecting her as Fiona believed she should. Fiona ultimately died when The Star sank and became a vengeful spirit attached to her locket which was eventually recovered from the wreckage.
In 2016 and 2017, Fiona reemerged as a vengeful spirit targeting teachers who ended up with her locket, seeking revenge upon all teachers for Mistress Aloway's failure to protect her. Fiona's murders drew the attention of hunters Sam and Dean Winchester who made the connection to The Star and found Gavin with the help of his grandmother, witch Rowena MacLeod. With Gavin's help, the Winchesters realized that Fiona was the ghost they were dealing with and helped Gavin to make contact with Fiona through a séance who explained to Gavin what had happened to her.
As the Winchesters tried to figure out what to do, they realized that the best option would be to send Gavin back to 1723 so that he could protect Fiona aboard the ship and restore the original timeline, an act that would erase Fiona's murders from existence. Gavin, who had never felt like he belonged in the 21st century, agreed with this. Using the Blood Sigil tweaked by Rowena, Gavin was returned to 1723, taking with him the locket and Fiona's ghost.
After Gavin was returned to his own time, the Winchesters checked the news stories and discovered no sign of Fiona's murders with all of her victims being alive again, confirming that Gavin succeeded in protecting Fiona and erasing this timeline. The only ones who remembered it were the Winchesters, Rowena and Crowley.
- Gavin MacLeod is abducted from 1723 to 2014 by the Knight of Hell Abaddon. After her death, he is not sent back to his own time.
- As a result of Gavin's disappearance, he does not board The Star when it sets sail nor is he present when his fiancé Fiona Duncan arrives at his home.
- Fiona chooses to stowaway aboard The Star anyway, but without Gavin to protect her, she is brutalized by the passengers and crew.
- Fiona becomes a vengeful spirit after her death targeting teachers due to Mistress Aloway encouraging her treatment.
- Several teachers are murdered in 2016 and 2017 due to Fiona's vengeful acts.
- Only the events surrounding Gavin MacLeod and Fiona Duncan appear to have been alternate to what happened in the original timeline. When the original timeline is restored, despite this timeline having technically begun the moment Gavin was taken in King of the Damned, all of the events remained the same aside from Fiona's murders as a vengeful spirit. This is because the alternate events were relatively self-contained, centering around Fiona's traumas before her death when The Star sank and when her locket was later recovered.
- Interestingly, Gavin's displacement to the 21st century did not seem to effect Bobby Singer's deal with Crowley and Bobby's efforts to break it. To break the deal, Bobby summoned Gavin's ghost to find Crowley's bones, capitalizing on Gavin's hatred for his father. Gavin being brought to the 21st century would've removed Bobby's ability to call upon his ghost in this timeline and when the original timeline was restored, Gavin had lost his hatred for his father due to his experiences in the present.