Supernatural: 10 Ways Bobby Got Worse And Worse

Bobby Singer is the surrogate father figure of Sam and Dean’s lives in Supernatural, especially after their father John Winchester dies. The brothers affectionately call him “Uncle Bobby” and he takes care of them even when they don’t want to be taken care of. He has a vast collection of lore books and occult objects that are used by everyone on the team to work cases.

Bobby’s past is tragic and he notes the things that have happened during the many times he crawls into a bottle or gets gruff with Sam and Dean. Through it all, Bobby is ultimately someone who operates in the shadows, and from the beginning, he gets worse and worse.

10 Never Set John Winchester Straight

Bobby is first introduced in Season 1 and he talks about the last time he saw John Winchester. He says that John left Sam and Dean with him for a month and didn’t contact them at all. He talks of other times John was hard on Sam and Dean. Later, through flashbacks, Bobby’s past with his own abusive father is revealed.

Throughout the show, Bobby shows how he sees Sam and Dean as his own sons and he knows what it’s like to grow up with that kind of stress. Yet, he never did anything definitive to set John Winchester straight.

9 No Formal Education For Sam And Dean

Bobby’s home is filled with lore books, weapons, and occult objects. When Sam and Dean bring Meg to his house and Bobby traps her with a Devil’s Trap drawn on the ceiling, they have no idea what it is.

They live their whole lives in the hunting life and Bobby had this knowledge all along but Sam and Dean never learned something as simple as using a Devil’s Trap until they’re adults.

8 Lack Of Protection

Meg the demon possesses Sam in Season 2 and Bobby helps exorcise her to save him. Then, he gives Sam and Dean each a charm that helps protect them against possession. John Winchester has known Bobby all their lives and he never had one of these charms. As vulnerable children who could have been used against John in the past, the never had one of those charms.

It wasn’t until after John was dead and Sam was possessed by a dangerous demon that Bobby came forward with this protection charm. Later, the brothers get tattoos. Bobby also goes on hunts for years, apparently without these protections, with Rufus, the Harvelles, and other hunters. He has the resources to protect them all the time but they still go without on a regular basis.

7 Refusal to Upgrade Technology

There are several times when Bobby struggles to understand what Sam and Dean are describing. He uses a flip phone and an old computer and prefers to use old books for research. The books are fragile and when his house is eventually burned down, they lose most of his library.

He refused to upgrade his technology and use better devices and systems that would have given all the hunters access to his collection at all times. He sits at home with landline phones and verifies hunters when law enforcement calls about their fake credentials. He laments working so hard and being trapped at his home to help all the hunters when he could have upgraded his technology and roamed free.

6 Took Rufus For Granted

Rufus is just as gruff as Bobby and there is an allusion to a hunt gone wrong in Omaha that sours the friendship between Rufus and Bobby but Rufus still shows up when called. When Sam and Dean are looking for the Colt, Bobby sends them to Rufus to get help.

During the Season 4 Apocalypse story arc, Rufus calls Bobby to talk about seals breaking. He helps them on numerous hunts and even steals a gem from a museum to help Bobby when asked. Still, Bobby scoffs at Rufus when he looks for praise. He never really says “thank you,” and he keeps on calling Rufus until the day he gets him killed.

5 Let Dean Stay Clueless

After the Apocalypse, Dean goes off to live with Lisa and Ben in suburban paradise and, according to Chuck’s narration, he doesn’t see Bobby for a long time even though Bobby continues hunting. He knew that Sam was back all along but didn’t tell Dean with the explanation that Dean “had it all” and they didn’t want to bother him.

Throughout Season 4 and Season 5, Bobby stresses the importance of everyone sticking together but when Dean thinks that Sam is dead for a year, Bobby lets him.

4 Gives Up Hope

Just after Lucifer is freed, Bobby is possessed by a demon and subsequently suffers a stab wound that renders him unable to walk and bound to a wheelchair. Almost immediately, he becomes so down on himself that he almost eats a bullet. He feels useless and doesn’t do much to help his situation aside from griping about being in a wheelchair.

After Jo and Ellen die while on a mission (one that they knew was incredibly dangerous), he burns the photo of all of them together. Later, he makes a deal with Crowley without worry that he might be double-crossed and regains the use of his legs.

3 Provokes Crowley

In his deal with Crowley, the contract was supposed to stipulate that Crowley was “borrowing” Bobby’s soul. After the apocalypse is averted, Bobby wants his soul back and Crowley says that the contract reads he only has to give his “best effort” to give it back.

Enraged, Bobby provokes Crowley and tortures other demons for information until he finds out who Crowley was before he died and became a demon and where his bones are buried. This is the action that pulls Crowley into their lives. It makes him interested in all of them. They have leverage against him because of Bobby.

2 The Risks That Got Him Killed

Castiel takes in the Leviathans and they attempt a world takeover with Dick Roman at the lead and Bobby appears to be even more pissed about it than everyone else. He takes a risk by keeping a Leviathan in his basement that could turn on him at any second.

He puts Frank Deveraux in danger by sending Sam and Dean their way. When they’re tracking a monster they believe to be a “Jersey Devil,” they find out about the Leviathan’s plans to farm humans as food. Bobby goes off on his own, is captured, and during his escape, he’s shot in the head.

1 Went Vengeful As A Spirit

Bobby didn’t go with his reaper after he died. He chose to stay behind and, with the help of a memento flask that Dean keeps, becomes a ghost. At first, it seems like he did it to stay with his boys and do everything he could to help them. But that wasn’t the real reason.

He wanted revenge on the Leviathan leader that killed him, Dick Roman. Bobby knew what happens to spirits when they stick around. He kept on going anyway until he possessed an innocent hotel maid to get to where Dick Roman is and take his shot before Sam and Dean can do it. As a ghost, he was worse than ever.

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