Henry Winchester

"You’re also Winchesters. As long as we’re alive there’s always hope. I didn’t know my son as a man, but having met you two, I know I would have been proud of him."

- Henry to Sam and Dean

Henry Winchester was a member of the Men of Letters. He was the father of John Winchester and the paternal grandfather of Dean, Sam, and Adam Milligan.

Season 8
Henry Winchester mysteriously appears in Sam and Dean's motel room while searching for his son John, and while escaping from a demon named Abaddon.



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.

Season 9
In Blade Runners, when Sam and Dean visit Cuthbert Sinclair aka Magnus, they identify themselves as Men of Letters and Henry's grandsons to get him to let them into his secret lair. Magnus reveals that he was Henry's mentor in the order before he was kicked out and that Henry, who he referred to as a rebel, used to visit him all the time.



In Mother's Little Helper, in flashbacks to 1958, Henry and Josie Sands travel to Milton, Illinois on a field mission shortly before their initiation to investigate violent deaths caused by otherwise normal people. Henry expresses doubt about being a Man of Letters due to the danger of dying and leaving his wife and son alone. Henry and Josie eventually determine demons are behind it and exorcise two, but one, Abaddon, proves to be immune and knocks Henry out. Abaddon initially plans to possess Henry to infiltrate and destroy the Men of Letters, but Josie convinces Abaddon to take her instead. After having the only other surviving demon play dead, Abaddon wakes up Henry and pretends that they defeated all of the demons. Believing the case to be over, Henry leaves with Abaddon, his doubts about being part of the order gone after seeing how they can save lives as part of it.

In King of the Damned, Abaddon shoots Crowley in the shoulder with a devil's trap engraved bullet to disable him while she fights Dean, something she tells him she learned from Henry. In the fight that follows, Dean kills Abaddon, avenging Henry's death.

Season 12
In Family Feud, Gavin MacLeod uses the Blood Sigil to return to his own time and asks if it will work for him. Dean notes that both Henry and Abaddon successfully used the spell in the past.

Powers and Abilities
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, such as the Sleep Spell and blood sigil, 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 Winchester without them even noticing.
 * Basic Hunting Skills - Despite looking down on hunters, Henry had at least some basic hunting skills. This can be seen with his investigation into the events at St. Bonaventure Convent and his ability to perform an exorcism and create a devil's trap in the form of a bullet.

Appearances

 * Season 4
 * In The Beginning (Mentioned only)


 * Season 8
 * As Time Goes By
 * Clip Show (Flashback)


 * Season 9
 * Blade Runners (Mentioned only)
 * Mother's Little Helper
 * King of the Damned (Mentioned only)


 * Season 11
 * Alpha and Omega (photo)


 * Season 12
 * Family Feud (mentioned)