Bobby Singer was one of the main protagonists in the horror TV series Supernatural. He was an old family friend to the Winchesters and a close ally and eventually father figure to Sam and Dean after John Winchester's death. He was played by Jim Beaver.



Bobby's guilt over Karen's death causes her to inhabit his dreams. She is later resurrected by Death and turns into a zombie and he has to kill her again, which causes him more grief.

Bobby has known the Winchesters since at least 1991.He gave an 8-year-old Sam an amulet as a Christmas present for his father, which he eventually gave to Dean. Bobby also played catch with Dean  and took the brothers deer hunting. John Winchester and Bobby were not necessarily on good terms. Dean comments that the last time Bobby saw John he nearly "filled him with buckshot." It is to Bobby's place that Sam and Dean go to grieve after John's death. After this Bobby's relationship with the Winchesters grows even closer, and he becomes both father figure and friend.

When Sam and Dean try to go after Lilith without him, Bobby tells them "Family don't end with blood, boy  and more than once Dean tells Bobby he's like a father to him. Bobby has listed Dean as his official next of kin. In 2009, Bobby is paralyzed from the waist down after stabbing himself with Ruby's knife to overcome his own demonic possession when Meg orders him to kill Dean.

Bobby sells his soul to Crowley in exchange for information on Death's location. Crowley also makes it possible for Bobby to walk again. He says that he will return Bobby's soul after Lucifer is defeated. It is later revealed that Bobby was given the standard ten years to live until his soul is dragged to Hell. Bobby is able to trick Crowley and negotiate the return of his soul.



Bobby is the first one to voice concerns about Castiel's activities, and is with Sam and Dean when Castiel appears. He helps to send the souls back to Purgatory, and tries to keep Sam and Dean grounded in the aftermath of losing Castiel, Sam's hallucinations, and the appearance of the leviathans.

After being shot by Dick Roman, the leader of the Leviathans, Bobby lapses into a coma and dies. His last word is an affectionate "Idjits" to Sam and Dean. However, Bobby refuses to go with his reaper, remaining on Earth as a spirit to help the Winchesters, when he is able. However, after becoming vengeful spirit temporarily, he asked Sam and Dean to put him to rest, which they did. His last request was for them not to give into vengeance like he did and when their time came, to move on.

Unfortunately, instead of going to Heaven where he belonged once his flask was burned, on Crowley's orders, rogue reaper Ajay takes Bobby to Hell instead where he is tortured by demons in the visage of Sam and Dean taunting him. Eventually, the real Sam rescues him and releases Bobby's soul unto Heaven where it belongs with help from the angel Naomi.

Life & Habits

Since the death of his wife Karen Singer, the only other romantic interests in Bobby's life that we've met are Eleanor Visyak and Annie Hawkins. His neighbor Marcy Ward expresses an interest in him, but a messy incident with an okami ends any possibility of a relationship.

Bobby has extensive knowledge of the supernatural, and is well-known and generally well-regarded by other hunters such as Gordon Walker, Kubrick, Rufus Turner, Olivia Lowry, Isaac and Tamara among others. He also knows Ellen and Jo Harvelle. According to Jo's Journal, Bobby frequented the Roadhousefrom around 1993.

Bobby's reputation around Sioux Falls is that of a troublesome old drunk, but following his role in quashing a zombie uprising, the local sheriff, Jody Mills, comes to develop a friendship with him, that appears to have the potential to become romantic; with one kiss is exchanged prior to his death.[9]

Bobby reads and speaks Japanese and has visited Japan.  He also speaks a few words of French.



Bobby owns Singer Salvage Yard (also seen written as Singer Auto Self Service Salvage Yard, on a sign in 2.02 Everybody Loves a Clown), and lives in a house on the premises. It is located in South Dakota (as confirmed by Dean), near the town of Sioux Falls.

Bobby has lived at Singer Salvage Yard since he was married to Karen. It is here theImpala is towed after she is wrecked, and where Dean repairs her on at least three occasions.


The basement is an unfinished storage space except for a large ghost and demon proofpanic room, which Bobby built during “a weekend off.” Over time, Bobby has made other modifications to the house. Sometime after 5.15 Dead Men Don't Wear Plaid, Bobby placed a trap door in front of the hall closet that can be triggered by a lever inside the closet. The trap door opens into the basement, which he equipped with a steel core door and titanium kick plate.

He had a dog called Rumsfeld who was killed by Meg.

Bobby owns a blue Ford tow-truck with Lawrence County, South Dakota plates: 9NO-3L1. This is probably a reference to Jim Beaver's role in the HBO Western drama Deadwood. Deadwood is the county seat of Lawrence County. In season three he also drives a 1971 Chevelle.

Bobby gets people to drink holy water to test whether they are possessed - he first does this to Dean when he and Sam are trying to find where Meg is holding their father.  He gives Sam beer laced with it when Sam is possessed and Ellen has to drink a holy water shot after she escapes the demon attack on the Roadhouse. When Dean returns from the dead in 4.01 Lazarus Rising, Bobby throws holy water in his face, even though Dean has cut himself with a silver blade to show he is human.

In season seven, the house was burned down by the Leviathan Edgar.

In 8.23 Sacrifice, Sam and Dean return to Bobby's to make a deal with Crowley. They find the place abandoned and rusting.

"The storm’s coming, and you boys, your daddy – you are smack in the middle of it."







"Hey, save it! Let's just get the hell out of dodge before somebody finds that body."



"Hope to hell you boys are ready. 'Cause the war has just begun."


When Ellen appears, having escaped the demon attack on the Roadhouse, Bobby makes her drink a shot of holy water to ensure she is not possessed. Bobby is part of the effort to stop the opening of the Devil's Gate in Wyoming, and it is he and Ellen who actually close it.

We already did it your way. You burst in there half-cocked and look what happened! These demons haven't been topside in half a millennium! We're talking medieval, Dark Ages! We've never faced anything close to this! So we are gonna take a breath... And figure out what our next move is!"



"It's not a luck charm, it's a curse! She made it to kill people, Sam! See, you touch it, you own it. You own it, sure, you get a run of good luck to beat the Devil. But, you lose it, that luck turns. It turns so bad that you're dead inside a week."

After finding John's lock-up has been broken into, the boys contact Bobby, who confirms that he built the curse boxes, one of which has been stolen. Later, he explains the curse of the rabbit's foot and starts researching how to destroy it. During this conversation, he appears to be working on the Colt. After Belasteals the rabbit's foot, Bobby identifies her to Dean, and tracks down her address for him. Finally, Bobby provides Sam and Dean with a ritual which destroys the rabbit's foot and breaks its curse.

Bobby testing out the Colt.

"Well, it won't kill demons by then -- but I can promise you it'll kill you."




"You were possessed, baby. You were rabid. And I didn't know what I know now. I didn't know how to save you."






Bobby finds a way to locate Lilith. After giving her location to the boys, they obtain Ruby's knife and prepare to leave to go after her. Bobby has disabled theImpala, and argues that he must go with him, because "there's more to family than blood," and that they need him. After Dean kills a demon possessing a police officer, Bobby explains that because Dean is close to going to Hell, he is peering through the Veil and can see their true faces.


Bobby attacks the newly resurrected Dean.

"Yeah. Well, listen. No demon's letting you loose out of the goodness of their hearts. They've gotta have something nasty planned."


"So, you thought our luck was gonna start now all of a sudden? Spell's got to be cast over an open fire."

Sam and Dean are staying at Bobby's, discussing the implications of Castiel's revelations, when Bobby becomes concerned that a hunter and friend, Olivia Lowry, is not returning his calls. When the three go to check on her they find her dead, apparently from a supernatural being. When they find other hunters in the area also dead, they head back to Bobby's place.

Here they are confronted by the ghosts of people they all failed to save. Bobby is attacked by two young twin girls, who accuse him of failing to find and save them from a "monster." They hide Bobby in an old car in Bobby's yard, and are suffocating him when he is saved by Sam.

They take refuge in Bobby's panic room and Bobby determines they are dealing with Witnesses. They leave the room and he performs a spell to return the spirits to rest.


Sam calls Bobby, who thinks the boys are dealing with ghost sickness, in which a spirit literally infects a person with fear, which intensifies until the victim's heart gives out. Bobby theorizes that if the ghost that started the infection is destroyed, the sickness should clear up.

As Dean's "infection" worsens, Bobby meets Sam at the wood mill. Bobby reveals that he is fluent in Japanese, and identifies Luther Garland as a "burubaru," which can be killed with fear. Sam lures Luther out of hiding by destroying his drawings of Jessie O'Brien. He then wraps an iron chain inscribed with a spell word around Luther's neck, while Bobby drags him behind the Impala until he dissipates—a "terrible" plan that both dislike, but which they feel is their only option. Sam contacts Bobby to help with their case. He provides backup to Sam and Dean's FBI cover story by phone identifying himself as their superior, Mike Kayser. He identifies the culprit as a siren, which needs to be killed with a bronze knife dipped in the blood of someone under its spell. Just as Sam and Dean, both infected, are being forced to fight to the death, Bobby arrives, stabs Dean with a bronze knife and then uses it to kill Nick Munroe - the siren, saving Sam from being killed by Dean and breaking the spell over both. Bobby later comforts them on being tricked by the siren and berates them for not checking on Nick Munroe to see if he was actually real like Bobby did.


"The Apocalypse being nigh and all... is now really the right time to be having this little domestic drama of ours?"

Bobby helps Dean keep Sam in his panic room to help him withdraw from the effects of the demon blood. He gets a call from Rufus Turner alerting him that more of the 66 Seals have been broken. He challenges Dean a couple of times about keeping Sam locked up - he fears it may kill him. "He's like a son to me" he tells Dean. When Castiel releases Sam, Bobby catches him trying to sneak out and tries to stop him, but when he can't shoot him Sam gets away. As Dean takes off after him, Bobby begs him to bring him back, and not push him away.

"You stupid, stupid son of a bitch! Well, boo hoo, I am so sorry your feelings are hurt, princess! Are you under the impression that family's supposed to make you feel good?! Make you an apple pie, maybe? They're supposed to make you miserable! That's why they're family!"


"Well... We save as many as we can for as long as we can, I guess. It's bad. Whoever wins, Heaven or Hell, we're boned."

Bobby meets up with Sam and Dean, bringing the Impala with him, in order to help decode Chuck's message about "Michael's Sword." When Sam confesses that his killing Lilith freed Lucifer, Bobby coldly tells him that once the hunt is over, he wants nothing to do with Sam. Sam leaves to do some research. While researching further, Dean gets an idea, and going through some of John's old things. He finds a receipt for a storage facility that fits the message from Chuck.

Bobby attacks and restrains Dean - he too is possessed. A woman arrives with two henchman. It is Meg, the demon that once worked with Azazel and possessed Sam. Meg says the demons want Dean dead so he can't stop Lucifer. She orders the possessed Bobby to kill Dean with Ruby's Knife, but just as he is about to strike, Bobby manages to battle the demon and stab himself instead. Sam returns and helps dispatch the other two demons, but the Meg escapes by leaving her vessel.

Sam and Dean drop off a gravely injured Bobby at the hospital. When Zachariah tries to coerce Dean into allowing himself to be the archangel Michael's vessel, he offers to heal Bobby but Dean refuses.

Later a doctor tells Bobby he won't walk again. As the boys leave, Bobby tells Sam it was the demon talking earlier, and that he would never cut Sam out of his life.

"You're telling me you lost your mojo just in time to get me stuck in this trap the rest of my life?"

Bobby is still wheelchair-bound and in the hospital. He hasn't spoken in days. When Castiel turns up, Bobby asks to be healed, but Castiel says he can't - he is cut off from Heaven's power. Bobby gets pissed off at Cas and tells him that when he finds God, to ask him to heal Bobby.


"I ain't a hunter no more. I'm useless. And if I wasn't such a coward, I'd have stuck a gun in my mouth day I got home from the hospital."





"Not this guy. This is—this is the angel of death. Big daddy reaper. They keep this guy chained in a box six hundred feet under. Last time they hauled him up, Noah was building a boat. That's why the place is crawling with reapers. They're waiting on the big boss to show."


During the hunt, Dean contacts Bobby over a CB radio and informs him that Jo is badly wounded and they are trapped. Bobby has figured out that Lucifer is in town to raise Deathand warns Sam and Dean.


"I don't know if they wanted to take my life or... my spirit. Either way, they wanted me out of the way."


"That’s the round that I mean to put through my skull. Every morning, I look at it. I think, 'Maybe today’s the day I flip the lights out.' But I don’t do it. I never do it. You know why? Because I promised you I wouldn't give up!"


"You can't do it. What I did was a million-to-one, and that was some pissant demon I was brain-wrestling. You're talking about taking back control from Satan himself."




"Then you know Sam will beat the Devil... or die trying. That's the best we could ask for. So I got to ask, Dean. What exactly are you afraid of? Losing? Or losing your brother?"


As they prepare to go and stop the distribution of the Croatoan virus, Castiel laments his new found humanity and how useless he now feels, although Bobby quickly reprimands him for these thoughts considering he is still trapped in a wheelchair. Sam ponders how complicated their lives have gotten, and remembers the old days when they used to "just hunt wendigos." Crowley gives Dean Death's scythe in order to kill Death and also reveals that he gave Bobby back the use of his legs in their deal.


After Dean has obtained Death's ring, Dean places the four rings in position and they immediately magnetize. Dean tells Bobby he actually lied to Death about being okay with Sam saying "yes." Although Dean says they can't believe Death, Bobby is not so sure. Bobby tells Dean that he watched Sam save almost a dozen people back at the warehouse and he never let up for even a moment. He admits to Dean that they've always been unjustly hard on Sam even though, through all the criticism, Sam has been fighting hard since he was twelve years old.


"There was never much hope to begin with. I don't know what to do."




After Sam throws himself with Lucifer and Michael into Lucifer's Cage, Castiel reappears, his angelic powers restored. He heals Dean and resurrects Bobby. Chuck tells us in voiceover that Dean and Bobby won't see each other for a very long time, and that a week later Bobby will be hunting a rugaru outside Dayton.


When they are attacked by djinns, Dean takes Lisa and Ben to Bobby's home for protection. He is shocked to learn Bobby has known that Sam has been back for a year.

"Let me get this straight – we just 'saved the sodding world together,' and you're too good to drink with me?"



After killing the demon, Bobby answers phones and backs up other hunters posing as various law enforcement until Rufus knocks on his door. Rufus needs Bobby's help burying the body of an okami. They bury the body on Bobby's property and Rufus leaves just before Sheriff Jody Mills shows up with an FBI agent, Agent Adams. Agent Adams is looking for Rufus. Dean calls while the FBI agent is there and asks for help killing the lamia because they couldn't kill it with a silver knife blessed by a priest. Bobby tells him to find salt and rosemary and "blend the herbs, sauté over a high heat, and cook well," and hangs up when Dean kills the lamia. Agent Adams is persistent, and Sheriff Jody Mills tries to distract him, but Adams finds the spot where the Okami was buried. Fortunately, there is no longer any evidence of a crime because the okami is gone. Unfortunately, Rufus didn't stab it enough times to kill it, and it is loose.

While Bobby was interrogating the crossroads demon, Marcy Ward rang his doorbell with a homemade peach cobbler. She has been his neighbor for six months now, and seems to be interested in him romantically, asking him over for dinner and a movie and then, when he seemed hesitant, asking him to come over and take a look at her wood chipper, which has broken down. When he learns that the okami might be after her, he breaks down her door with a shotgun, scaring her, but drawing out the okami, which had been waiting in her bedroom to kill her. He kills the okami by pushing it through Marcy's (obviously functioning) wood chipper, and Marcy is covered in blood. Bobby still tries to salvage a relationship with her, but she turns him down. Afterwards, Rufus thanks Bobby for helping him with the Okami and tells him what his contacts in Scotland have learned about Fergus MacLeod, aka Crowley. Crowley had a son named Gavin MacLeod, who's signet ring is now on display in a museum in Andover. Rufus steals the ring for Bobby, but is arrested.



"Yeah. I'll hit the books, hard. Just don't shoot him yet, all right? Watch him. We need facts. 'Cause if it ain't Sam... we don't know what it is. And if we're gonna put him down, we need to know how."


After Dean invokes Veritas' curse, he calls Bobby to test it. Bobby is compelled to tell Dean a few interesting truths, including the fact that Bobby occasionally gets a pedicure, that he is a fan of Tori Spelling, and that Dean is his favourite of the two brothers (Although Sam is the better hunter at the moment). Dean hangs up when Bobby starts discussing his first girlfriend, who "turned out to be a-"


"Ain't nobody killing me in my house but me. I don't want to blow your legs out, boy, but I will."






"I'm glad he's better. I really am. But... That kid went straight-up Menendez on me not ten days ago. And now it's all just... erased? Sorry. I'm having a bit of a hard time even looking at him."





Bobby, Sam and Dean standing over Rufus' grave.

"No, we haven't. I never said I'm sorry, Rufus. I - you lost her because of me, and I -"






"I'm still kickin', Annie Oakley. Be back good as new in... a decade or two."





"Come on. You don't let Sam and Dean Winchester do squat. They got what they gotta. You know that. Anyway, we want Eve, we need coordinates. So we can stand here bellyaching or we can go poke that pig 'til he squeals. Thoughts?"




"But if we ain't... If there's a snowball of a snowball's chance here... that means we're dealing with a Superman who's gone dark side. Which means we've got to be cautious, we got to be smart, and maybe stock up on some Kryptonite."


"I know him, El. He's gonna figure it out. One way or another. Now, the only way I can stop him is to get ahead of him, so I need to know how you open the door."



"You know, this is exactly what Cas wants. For you to fall to pieces. Just try to think of what Sam would want."




"What we've got to do is hunt the son of bitch. Unfortunately, I lost my God guns."



"Well, either Sheriff Mills is having an ObamaCare-insured opium dream, or something’s eating folks down at Sioux Falls General Hospital."




"Well, consensus is they're, um, they're like shapeshifters only a lot more into eating folk. And nothing can kill 'em."


Three weeks later, Bobby is in hiding with the brothers at Rufus's cabin in Montana. He is maintaining contact with his network of hunters to follow the Leviathans' movements. Bobby leaves the brothers to start reassembling the library he lost in the destruction of his house; Bobby kept copies of his rarest books hidden.






"Don't open it. Even if it starts talking. Especially if it starts talking. When you cross over Underhill Bridge, just toss it in the drink. If you'll excuse me, I, um... I got a body to bury in cement."







Suspicious of Sam's marriage to Becky Rosen, Dean calls Bobby for help, but Bobby is hunting a major nest of vampires in Oregon so he sends Garthinstead despite Dean's reluctance to have another hunter that isn't Bobby help him.






"You did what you had to do. This is where you learn that... they pretty much never say thanks when you save 'em. Now go get a shovel. Bury the old man out behind the woodshed."






Young Bobby in 7.10 Death's Door.


Bobby turns back to the kitchen, and opens the door.



"Idjits." - Bobby's last words.





"I’m right here, you idjit! Balls!"











"No, wait, boys, you can't just break in. They know your mugs. What if we mailed in the flask? Then I could ghost through the joint. I mean, it's not like Dick can kill me twice. What, you got a better plan? Come on. Just because I'm dead doesn't mean I don't know how to do my damn job."



"I'm in the Veil. My Brad Pitt days are over. Now, the kid says that the only way to kill Leviathan is with a bone washed in the three bloods of the fallen. It's got to be from a human as light and good as the Leviathan are hungry and dark."

Sam and Dean struggle to understand what exactly the Word of God mean. Bobby appears before Dean saying he feels stronger than ever and tells him that they have to obtain the blood from the ruler of fallen humanity from Crowley. Then suggest that they also need to bleed an Alpha. When Dean tells him that the only Alpha they knew is dead, Bobby breaks the mirror and insist on going after Crowley.

Later at the Alpha's residence Bobby decides to scout the mansion and finds dead vampires and a scared girl. After boys drop her off at the hotel, they decide to also leave the flask behind to prevent Bobby from going vengeful. When they leave and the girl turns out to be cooperating with vampires, Bobby is left alone in a room with TV news talking about Dick Roman. He snaps, takes the flask and possesses a maid named Louise to seek out revenge on Dick on his own.

"What? Going vengeful? It's an itch you can't scratch out. Look... I'm done. Go get Dick. But don't do it 'cause you think it'll scratch the itch. Do it 'cause it's the job. And when it's your time... go."

Still possessing Louise, Bobby buys a machete and accidentally exorcises himself by grabbing a metal bar while trying to break into and steal a truck. Bobby tries to explain to Louise, but loses control again after seeing a newspaper talking about Dick and possesses Louise again. Bobby makes his way toSucroCorp where Sam tries to stop him, however Bobby is too far gone and tries to strangle Sam to death for his interference. However, when Bobby sees his reflection and realizes what he's become, he abandons Louise's body with a scream.

Bobby later reappears while Sam and Dean are trying to figure out which Dick is which from security cameras and angrily closes the laptop lid. Bobby tells them that while he has regained control, it's like "an itch you can't scratch out" and fears he will lose control again. Bobby asks Sam and Dean to burn his flask and to kill Dick, but for the job not vengeance like he tried. He also tells them to move on when they die and not stay like he did. They comply with his wishes and sadly watch as Bobby goes up in flames after promising to see them on the other side, but hopefully not too soon.

Garth has taken up Bobby's place since Sam and Dean disappeared for a year. He carries multiple cell phones around, presumably like Bobby's phones and gives advice like Bobby did, wears one of Bobby's old hats sometimes and uses some of Bobby's old phrases. According to Garth, he does this to honor Bobby who didn't just belong to Sam and Dean, he belonged to everyone. While searching for information on the type of ghost they are dealing with, Dean and Garth find what they're looking for in Bobby's Journal where he describes that a ghost leaving behind green goo is a spectre and how the one he encountered was awakened by his grave being desecrated, allowing them to figure out who the ghost is and deal with it.

During a case dealing with witches, Sam and Dean make a witch-killing spell to deal with the evil witch that they learned from Bobby. Dean comments that they've never actually seen the spell Bobby taught them work. Looking for possible information to exonerate their friend James Frampton, Dean searches through Bobby's files and finds a spell a witch can use to implant a false memory into another witch, showing that it is possible that James is innocent. In the end, the spell Bobby taught them works and Sam and Dean are able to kill the witch responsible, Spencer.

"I know that agreement. I taught you that agreement. That's a non-agreement. I get the feeling a lot must have happened while I was gone. Sam!"

After learning that for the second trial to close the Gates of Hell Sam needs to rescue an innocent soul from Hell and release it into Heaven, Sam and Dean approach rogue reaperAjay for help in sneaking into Hell. Ajay reveals that when Bobby's flask burned, he took Bobby to Hell instead of Heaven on Crowley's orders, making Bobby the perfect candidate to be rescued.

With Ajay's help, Sam makes it into Hell through Purgatory and finds Bobby who attacks him, believing that he is just another demon taking on Sam's form to taunt him. Using things only the real Sam would know, Sam convinces him of his identity and Bobby hugs him before asking if Sam is there because he died. After being told that it is a rescue, Bobby eagerly leaves his cell with Sam and is given Ruby's knife to defend himself. When three demons attack, Bobby kills two, but gets confused as the last demon takes on Sam's form. Taking a guess, Bobby stabs one and luckily kills the demon and not Sam.

Bobby and Sam escape Hell into Purgatory, but find no sign of Ajay and are trapped as Crowley has killed him. Sam explains to Bobby what happened while he was in Hell and Bobby is shocked to find out that Dean survived a year in Purgatory and Sam didn't look for him. When Sam explains that he and Dean have agreed never to look for each other if separated like that, Bobby reminds him that Bobby himself taught them that rule and that it is crap. The two are attacked by three vampires and one gets the drop on Bobby, but he is saved by Benny. Bobby wants to attack Benny and is shocked when Sam introduces him as a friend of Dean's, not understanding how Dean has a monster friend. Benny leads them to the portal out where Bobby enters Sam's arm for the trip to Earth after being warned not to stick around for another goodbye when he is released. Thanks to Benny sacrificing himself to hold off more vampires, Sam escapes to Earth with Bobby's soul.

On Earth, Sam casts a spell and releases Bobby's soul towards Heaven, but his soul is intercepted by Crowley who intends to take him back to Hell. Unexpectedly, the angel Naomi intervenes, drives off Crowley and releases his hold on Bobby's soul, allowing Bobby to finally ascend into Heaven where he belongs.


When Sam is in a coma and near death, his subconscious desire to die and move on manifests in the form of Bobby. When "Dean," Sam's desire to live manifesting itself talks back against him, "Bobby" causes him to disappear, leaving him alone with Sam. "Bobby" talks with Sam about how he has saved many lives and his life isn't for nothing. "Bobby" leads Sam to a house in the woods where he says what Sam needs to move on is before being killed by "Dean" who tries one last time to convince Sam to fight. However, Sam decides to take "Bobby's" advice and die.

Nearly 20 years ago Bobby killed a shapeshifter who had impregnated Bunny LaCroix, and killed her husband while trying to take the daughter Bunny had with him. Bobby agreed not to kill the baby, Olivia on the condition that Bunny lock her up for everyone's safety. Bunny complied and asked Bobby to take care of her daughter if anything ever happened to her. Her great-nephew Dash later said that Bobby apparently meant a lot to Bunny for this.

In 2014, Bunny dies and leaves Bobby the pendant that acts as the key to the attic where Olivia was imprisoned. After finding the message from Bunny's lawyer on Bobby's old cellphone, Sam and Dean go to claim his inheritance and discover his history with Bunny and Olivia. Olivia didn't see Bobby's mercy as a good thing due to being locked up and wanted revenge on him by killing Sam and Dean since Bobby was dead. Olivia also began to kill her family out of disgust towards them and their greed. In the end, Dean was forced to kill Olivia and finish what Bobby started.



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