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The MacLeod Family is a Scottish family.
- Unnamed tanner (deceased) - Rowena's father and Crowley's grandfather, he was a man from Scotland who worked as a tanner. Little is known about him, aside from the fact that he bears a resemblance to his great-grandson, Gavin.
- Crowley's father (deceased) - A rich human who impregnated Rowena, only to abandon her and return to his wife shortly after the child's birth. His abandonment of Rowena drove her to despise love and desire power instead. His son Fergus never met him.
- Rowena MacLeod (deceased) - A powerful witch who has been alive for more than 300 years. She is also a former member of the Grand Coven. Like her son Fergus, she is an on-and-off ally of the Winchester brothers. She shares a turbulent relationship with her son and for most of her appearances, she does things based solely on self-interest. She was killed twice by Lucifer in 2016 and 2017 but was resurrected. In 2019, Rowena sacrificed herself to save the world from the unleashed souls of Hell, leaving the family extinct. After death, Rowena becomes the new Queen of Hell as a damned soul.
- Crowley (deceased) - Fergus Rodrick MacLeod, is the son of Rowena, by whom he was abandoned when he was only a child. He grew up had a son who he abused and sold his soul to a crossroads demon, he died in 1723 and became King of the Crossroads, and later, King of Hell. He is one of the Winchester brothers longest-lasting allies as well as enemies. Sacrificed himself to seal Lucifer in an alternate reality.
- Gavin's mother (deceased) - An unnamed woman who was the mother of Gavin MacLeod by Fergus. Little is known about her besides Gavin becoming a trading ship captain only after both his parents were dead.
- Gavin MacLeod (deceased) - Fergus's son whom he abused during each other's lifetimes. Gavin later became the captain of a trading ship known as The Star, only to die when the ship sank in 1723. His ghost was briefly summoned in 2009 by Bobby Singer. In 2014, Abaddon brought him to the present timeline, where he remained until 2017, having chosen to go back to prevent his fiancé Fiona from becoming a vengeful spirit.
- Sam and Dean Winchester - The brothers are on-and-off allies with the members of the MacLeod family. They have known Crowley since the days of the The Apocalypse and they met Rowena in 2015. The brothers usually call upon either Crowley or Rowena whenever they need assistance.
- Fiona Duncan (deceased) - Gavin's fiancé who, upon Gavin's disappearance, boarded The Star only to be brutalized and raped by the crewmen before the ship sank. She returned as a vengeful spirit and punished every teacher she could find. Gavin decided to return to the past in order to prevent her suffering. They died together when The Star sunk with both of them on board, as fate had intended.
- Demons - As King of Hell, Crowley took charge of most of the demons, with only a few going rogue or choosing Abaddon, and later, Lucifer's side. They do not respect Crowley much but they do as they are told anyway.
- Castiel - A reluctant ally of Crowley and Rowena. The angel joined sides with Crowley in hopes of obtaining the souls of Purgatory and win the Second Heaven Civil War. The two had a falling out, but remained allies in a bid to defeat the Leviathans, and later on, whenever Sam and Dean needed their assistance. Castiel's alliance with Rowena is based solely on Sam and Dean's request, and they do not have a good relationship. Rowena once cursed Castiel with the Attack Dog Spell, causing him to go on a wild rampage, until she was forced to undo the spell.
- Oskar (deceased) - The son of a peasant Polish family who gave shelter to Rowena 300 years ago. Rowena thanked them by curing Oskar of an illness and granting him immortality. Rowena loved Oskar as a son, but was forced to kill him as part of a ritual to remove the Mark of Cain. Rowena got her revenge by allowing Gavin to return to the past against Crowley's wishes.
- God - God favored Rowena and never had any sort of conflict with Crowley even though he stated to "rooting against them". He formed a team against Amara with both Rowena and Crowley as vital members. In the aftermath, God and Rowena bonded over their shared opinion on children, while Crowley promised not to call God "dad" as a result.
- Lucifer (deceased) - Crowley's competitor for the throne of Hell and his enemy since the time of The Apocalypse. Unlike most demons, Crowley turned against Lucifer and helped the Winchesters because he knew Lucifer would annihilate the demons as well. The defeat of Lucifer gave Crowley the throne up until 2016, when Lucifer escaped his Cage with the help of Rowena. Lucifer retook the throne and turned Crowley into a prisoner. Lucifer also killed Rowena, but she was revived through magic. The three joined sides temporarily to deal with Amara, after which Crowley hunted Lucifer down and eventually, with Rowena's help, captured him, and made him a prisoner. Lucifer later killed Rowena temporarily again and Crowley sacrificed himself to seal Lucifer away in an alternate universe. Lucifer was killed by Dean Winchester in 2018 while Dean acted as the vessel for the Apocalypse World Michael who gave Dean the power to kill Lucifer.
- Abaddon (deceased) - A Knight of Hell who tried to overthrow Crowley in 2014, going so far as to kidnap Gavin from 1723 and bring him to the present as a bargaining chip. She tortured Gavin briefly but Crowley was unfazed. Crowley assisted Sam and Dean in obtaining the First Blade, which was used to kill her.
- Demons - Rowena finds them troublesome and has on more than one occasion, killed them for her own protection. Whenever in conflict with Crowley, the demons also openly spy on or capture Rowena.
- The Loughlin Family (extinct) - Rowena had once sought refuge with this family, only to be cruelly turned down. Years later, Rowena confronted them again in a bid to free Dean from the memory curse cast upon him by Gideon Loughlin. The effort nearly resulted in Rowena's death at the hands of Catriona Loughlin, but Dean killed both Catriona and her brother Boyd, rendering the family extinct.
- The Darkness/Amara (formerly) - Crowley originally took care of Amara in hopes of gaining favor, until she chose Dean over Crowley. Rowena herself also sought an alliance with Amara out of personal interest, but became terrified after Amara was restored to full power. Both Crowley and Rowena assisted God in weakening Amara so he could imprison her. When the plan failed, the two awaited for Dean to kill Amara. In the aftermath, they are probably happy she is gone.
- British Men of Letters - They had formed a witch hunt and chased Rowena from her home in Scotland, forcing her to flee to Europe while she left her son Fergus behind. As King of Hell, Crowley held a loose deal with them but was shown to be unhappy about it and eager for the deal to be ended.
|Rowena's father †|
|Rowena MacLeod||Crowley's father †|
(Fergus Roderick MacLeod) †
|Gavin MacLeod †||Fiona Duncan †|
- This family is unique in that it consists of a witch, a demon, and a ghost, albeit briefly.
- Only Gavin and Rowena have openly used the surname. Crowley prefers to stick with his current name. He has on one occasion used his middle name "Rodrick".
- All primary members have died at one point, with Crowley returning as a demon and Rowena resurrecting herself through magic. Gavin briefly returned as a ghost and was able to live beyond his years through time travel.
- Due to Crowley's status as King of Hell, his mother has been referred to as "Queen Mother" and Gavin as "Prince of Hell".
- This family was extinct as of the Season 12 finale.
- By Season 15, with Rowena's death at the hands of Sam Winchester, the family is extinct.
- Two members of the family have become the Ruler of Hell.
- Crowley took power following the failed Apocalypse.
- After dying for a final time, Rowena takes power as a damned soul.