|Dates||???? - 2006 (killed by Meg)|
|Episode(s)|| 1.10 Asylum (voice only)|
Caleb is a hunter who lives in Lincoln, Nebraska. According to Jo's Journal, he frequented the Roadhouse between at least 1996-99. Caleb supplies fellow hunter and personal friend John Winchester with weapons and ammunition. However, they fell out of touch at some point in 2005 or 2006. Like Jim Murphy, Caleb is killed by Meg in November 2006 in order to coerce John into giving her the Colt.
Early in the episode, Sam is in the phone with Caleb to ask if he has been in contact with John, who has gone missing. However, Caleb has not heard from John in at least a few weeks, and apparently asks Sam where he and Dean knew John to have been last. Although he does not appear in person, Caleb's voice can be heard over the phone when he promises to contact Sam and Dean if he finds out anything about John's current whereabouts.
Caleb finds out that Jim Murphy is dead and looks into it, finding out that there were traces of sulfur found at Jim's church. He calls John up to tell him this. Later on, he is captured by Meg and becomes her hostage. When she calls John, she briefly lets Caleb talk to him to let John know which friend she is "visiting." Caleb seizes this opportunity to try to warn John not to give her the Colt, but she cuts him off before he can finish his warning. She then kills Caleb by slashing his throat open when John tries to pretend that he doesn't have the Colt, and holds out the phone so that John is forced to listen to the sounds of Caleb dying. John reluctantly agrees to give Meg the Colt so that she won't kill anymore of his friends, but secretly plans to double-cross her by giving her a fake Colt while Sam and Dean use the real one to kill Azazel. At the site where John is supposed to give Meg the Colt, she taunts him by reminding him of how she killed Caleb and Jim and wants to kill more of his friends.
- Judging by his arsenal and references to him supplying John with munitions, Caleb is possibly some form of arms dealer.
- According to Jo's Journal, Jo was forced by her mother to refer to Caleb as "Uncle Caleb."
- Also according to Jo's Journal, Caleb also kept a hunter's journal.
This page was captioned "Caleb's Journal" and appeared in Jo's Journal attached to the January 4, 1996 entry.