Just 'cause Dim and Dimmer here can't keep their own family all in the same dimension, doesn't mean they can mess with mine!
- Rowena MacLeod - Mother of Fergus. Grandmother of Gavin.
- Fergus Roderick MacLeod aka Crowley (deceased) - Son of Rowena. Father of Gavin.
- Gavin MacLeod (deceased) - Son of Fergus. Grandson of Rowena.
- Fiona Duncan (deceased) - Lover of Gavin.
The known members of the Macleod Family originate in Northern Scotland. By 1661 in Canisbay, Scotland, Crowley's father had an affair with Rowena who conceived a son during a Winter Solstice orgy, but he abandoned her when her son was born. By the time Fergus turned eight, Rowena treated him with nothing but hatred, fed him whiskey to put him to sleep, and abandoned him in a workhouse. She decided to practice witchcraft and became initiated in the Grand Coven, but they soon banished her and placed magical bindings on her due to her magic being too extreme, and also as a punishment for sleeping with a non-magical person and giving birth to his son. When Fergus became an adult, he became a tailor and made a demon deal where he sold his soul in exchange for "an extra three inches below the belt." He fathered a son named Gavin whom he treated the same way Rowena treated him as a child. By 1723, Fergus had died in a gutter and Gavin had decided to sail to the New World to start a new, better life. He captained a brigantine called The Star that departed from a port in Leith, Scotland, and went down in a storm by Andover, Massachusetts. When he went to Hell, Fergus became a crossroads demon known as Crowley who worked his way up to the higher echelons of the demonic hierarchy and became the "King of the Crossroads" and right hand man to Lilith.
In 2010, Crowley lent his hand in the Winchesters' fight to prevent the Apocalypse by providing them with the Colt when they make an attempt to kill Lucifer and assistance in tracking down the Horsemen of Pestilence and Death, but he had to force Bobby to sell him his soul to locate Death. Despite this, he also restored Bobby's use of his legs (after he became paralyzed following a demon attack led by Meg) by adding a sub-clause to his contract on his behalf. After Michael and Lucifer were imprisoned, the Prince of Hell, Ramiel, persuaded Crowley to take control of demon-kind as King of Hell, which he accepted, passing his title as King of the Crossroads to Barthamus. Once in charge, Crowley decided to make radical changes to Hell, having people wait in an endless line as their torture, and having his minions track down and kill all of Lucifer's loyalists to prevent anyone from challenging him during his tenure.
A year after the Apocalypse ended, Bobby and Rufus recover Gavin's signet ring from the Maritime Museum in Andover, Massachusetts, where multiple artifacts from The Star were displayed after the wreckage was recovered 30 years prior. Bobby uses the ring to summon Gavin's spirit to uncover some serious dirt on Crowley's human life, including where Gavin buried him. After summoning Crowley, Bobby offers to give him his bones for the return of Bobby's soul and maintaining the use of his legs, a deal he reluctantly accepts. Crowley later teleports to Scotland, where Sam and Dean have already dug up his bones for incineration, to retrieve them and relocate them to a crypt in Guam.
In 2014, Abaddon kidnapped Gavin before he could get to The Star and dragged him to the present to use as a bargaining chip against Crowley. After reconciling, Crowley and Gavin developed a closer bond. After Abaddon's death, Crowley allowed Gavin to remain in the future as a chance to begin a better life.
Soon after, Rowena resurfaced to reclaim her lost power base and was subsequently captured by Crowley's demons. Rowena attempted to use him to go after Olivette, the rest of the Grand Coven, and the Winchesters, but Crowley was able to see past her deceit and evicted her from his hideout. They displayed nothing but contempt towards each other after that, but Rowena was able to help in removing the Mark of Cain, battling against the Darkness, and pursuing Lucifer. She had a hand in releasing Lucifer from his cage, but he snapped her neck to prevent her from reopening it and potentially sending him back. It is later revealed that she had a Resurrection Charm implanted in her thigh that would bring her back to life if she is ever killed. Ever since the betrayal, she held a personal vendetta against him and wished to send him back to the Cage.
As a consequence of Abaddon taking Gavin out of time, his lover Fiona Duncan snuck aboard The Star, unaware of what happened to him. Suffering weeks of abuse, Fiona died when The Star sank off the coast of Massachusetts. In 2017, she became a vengeful spirit targeting teachers. In order to reverse the effects of his being sent forward in time, Gavin decided to return to 1723 to spend eternity with her and prevent her from going vengeful.
The Winchesters, Castiel, Rowena, and Crowley seemingly sent Lucifer back to his Cage, but Crowley perverted Rowena's spell, sending him to his original vessel, Nick, in the Needham Asylum. Crowley had him wrapped in chains made from the same material used in the Cage and his reconstituted vessel warded with sigils from the Cage at the molecular level. Despite these security measures, Lucifer was able to regain control of his vessel with assistance from the demon Drexel and seemingly kill Crowley who narrowly escapes death by possessing a rat. Soon after, he realizes that he has been trying so hard to keep his job as King of Hell that he never realized that he hated everything about it. Growing tired of the machinations of Hell, Crowley offers to seal the Gates of Hell as retribution against the rest of demon-kind for their constant treachery. He decides to help the Winchesters trap Lucifer for good by using himself as the final ingredient, sacrificing his life to imprison Lucifer in Apocalypse World before he can get to his newborn nephilim son -- Jack Kline.
Before Lucifer went to North Cove, Washington, to find his son, he killed Rowena again and incinerated her body to keep her dead, but she used her resurrection charm again to return to life. She later convinces Sam to give her a page from the Black Grimoire to lift the Grand Coven's bindings and restore her to full power. She is shown to grieve Crowley's death and resent herself for abandoning him for her pursuit of magic, but she later decides to help Sam and Dean in the battle against the forces of Apocalypse World to search for redemption for her past actions.
- 11.10 The Devil in the Details
- 10.09 The Things We Left Behind
- 10.10 The Hunter Games
- 6.04 Weekend at Bobby's
- 5.10 Abandon All Hope...
- 5.20 The Devil You Know
- 5.21 Two Minutes to Midnight
- 12.12 Stuck in the Middle (With You)
- 13.08 The Scorpion and the Frog
- 6.10 Caged Heat
- 6.20 The Man Who Would Be King
- 9.21 King of the Damned
- 10.07 Girls, Girls, Girls
- 10.16 Paint It Black
- 10.17 Inside Man
- 10.23 Brother's Keeper
- 11.22 We Happy Few
- 12.08 LOTUS
- 11.10 The Devil in the Details
- 11.18 Hell's Angel
- 12.13 Family Feud
- 12.15 Somewhere Between Heaven and Hell
- 12.21 There's Something About Mary
- 12.23 All Along the Watchtower
- 13.12 Various & Sundry Villains
- 13.19 Funeralia
- 13.21 Beat the Devil
- 13.22 Exodus