|Status||Deceased (killed by Abaddon)|
|Family|| John Winchester (son) † |
Dean Winchester (grandson)
Sam Winchester (grandson)
Adam Milligan (grandson) †
|Portrayed by:||Gil McKinney|
He was about to receive his final initiation when Abaddon infiltrated and murdered the elders of the Men of Letters. He was given the key to the Men of Letters headquarters, to be kept safe from Abaddon, which he took with him into the future in an attempt to avoid the Knight of Hell.
He meets his grandsons, Dean and Sam, in the year 2013. Henry hoped that even without his guidance from the past, he would still encounter John as a man and fully-pledged Man of Letters in the future. Eventually he discovers (to his shock) that, with most of the order's members killed, John went on his own path and became a Hunter, eventually taking his two children along in revenge for losing his wife Mary to a demon.
Henry tries to put right the estrangement from his son John by attempting to use the blood sigil ritual to return to 1958, but is stopped by Dean as this would change the past. Henry is a traveler out of time and although Henry is aware going back to put things right might alter the present, believes this is a necessary act. Dean disagrees and forces him not to go through with it.After Abaddon captures Sam, she demands a trade of Henry and the box containing the key. Henry and Dean come up with a plan to stop her: Henry carves a Devil's Trap into a bullet and shoots it into Abaddon's head when they make the exchange. This binds her to her body and limits her movements and powers, allowing Sam and Dean to cut her up into little pieces and bury her in cement, trapping her forever as they have no way of killing her. However, during the confrontation, Abaddon impales Henry in the stomach with her hand and he dies of his wound, but tells Sam and Dean he is proud of them and the man John became.
Powers and AbilitiesEdit
As a member of the Men of Letters, Henry had a number of abilities that allowed him to work with and against the supernatural. He was also well-versed with weaponry and was dexterous and intelligent enough to outwit his own grandsons and even a Knight of Hell. His notable skills include, but are not limited to:
- Soul Channeling - Henry could tap into his own soul to provide him with power for certain spells. This enabled him to use a blood sigil that sent him to the future to his grandsons.
- Spell Casting - Henry knew a number of spells that aided him in his tasks.
- Sleight Of Hand - Henry was able to escape a pair of handcuffs with ease and slip them onto Sam and Dean without them even noticing.
- Henry was the only Winchester able to travel forward in time under his own will and power. Dean was sent back to 1973, but this was not of his own free will. Later Castiel provides the means when the boys travel back in time to meet Samuel Colt and Dean is accidentally dragged along by Chronos.
- The basic issue at play in the episode is Dean's concern that having his grandfather return to 1958 will alter the present. Dean states that he and Sam prevented the Apocalypse. Henry sees this as a positive in that the "Apocalypse never occurs".