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|image= [[Image:Bobbydt.jpg|350px]]

|dates= August 12, 1950 - – 2012 (killed by [[Dick Roman]])

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Bobby has known the Winchesters since the late 1908s1980s. By 1989, John was leaving the boys in Bobby's care<ref>[[7.10 Death's Door]]</ref>. In 1991, he gave an 8-year-old [[Sam]] an [[Dean's Amulet|amulet]] as a Christmas present for his father, which he eventually gave to [[Dean]].<ref name="three08">[[3.08 A Very Supernatural Christmas]]</ref>. One at least one occasion, he took the brothers deer hunting.<ref name="seven09">[[7.09 How to Win Friends and Influence Monsters]]</ref> [[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."<ref name="one22">[[1.22 Devil's Trap]]</ref> 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.

After arriving in Heaven, Bobby enjoys his new life in his Heaven which is a replica of his old house until Sam and Castiel contact him for help with breaking [[Metatron]] out of prison in hopes of removing the [[Mark of Cain]] from Dean. Bobby, though he feels himself rusty, helps and is punished in an unknown manner for it, though he leaves Sam a note in which he states that it was worth it. He is subsequently locked up in Heaven's jail for his actions. Five years later, after dying for the final time, Dean is reunited with Bobby in Heaven. Bobby reveals that [[Jack]] released him from prison and reshaped Heaven to be a much better place with Castiel's help. Bobby describes the new Heaven to Dean and tells him about Dean's parents and Rufus as the two men share a beer outside of [[Harvelle's Roadhouse]] before Dean goes on drive through Heaven in the Impala.