|“||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 came from a long line of Men of Letters as his father and grandfather were both members that taught him in their way.
At some point, he married a woman named Millie and they had a son named John Winchester. Henry spent much time with his son taking him to a drive-in movie and buying him a music box. He intended to pass down his way of life to him.
Unfortunately, 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.
After Henry tries to steal The Impala (his family's car), he was captured by Sam and Dean who questioned as to how he knew their father which shocks him. He explains to them that he was about to receive his final initiation when Abaddon invaded and slaughtered his colleagues as well as forcing him to flee into the future.
He then learns John is dead and formally meets his grandsons, Dean and Sam, 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 in his old journal and that with most of the order's members killed, John believed Henry left him and went on his own path and became a Hunter, as well taking his two children along in revenge for losing his wife Mary to a demon before being killed by the same one.
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 even acknowledging he was wrong to believe that Henry abandoned John 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 is knocked out when he protests about his decision and after seeing Dean's determination to save Sam, he comes up with a plan to stop the demon. Henry carves a Devil's Trap into a bullet and shoots it into Abaddon's head when they make the exchange. This would bind her to her body and limits her movements and powers. However, during the confrontation, Abaddon reneges on the deal and impales Henry in the stomach with her hand but he shot her in the head. Abaddon found the headshot to be a "rush," but her good humor instantly disappeared once she discovered that the box she was given was a fake. Demanding to know where the real one was, she tried to read Henry's memories, but she was unable to do so much as move— as Dean and Henry had outsmarted her, and the bullet now in her brain had been engraved with a devil's trap. Dean then decapitated Abaddon, planning to cut her into small pieces and bury these pieces in cement to permanently trap her as they have no way of killing her.
Henry slowly dies of his wound, but not before he tells Sam and Dean he is proud of them and the man John became. He uses his final moments to give them the key as Sam and Dean are sad at his loss. The brothers then bury their late grandfather in the graveyard of the other deceased men of letters with his own personal grave marker.
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 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.
In Alpha and Omega, Henry is listed as one of the Winchesters' relatives on Lady Toni Bevell's wall. The wall incorrectly states that Henry was killed during his initiation massacre, showing they are unaware of the truth of his death.
During Lebanon, Dean and Sam mention Henry to John after he himself was taken out of time to the future. They explained the truth of his disappearance and their men of letters' legacy from him, as well as how they found the bunker because of him. Dean even stated Henry would be proud John finally made it to the bunker, as he was amused to hear this tale and seemed to understand his father's circumstances.
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:
- 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.
- 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.
- Spell Casting - Henry knew a number of spells:
- Season 4
- In The Beginning (mentioned only)
- Season 8
- Season 9
- Season 11
- Alpha and Omega (photo)
- Season 12
- Family Feud (mentioned only)
- Season 14
- Lebanon (mentioned only)
- Henry was the only Winchester able to travel forward in time under his own will and power. Dean was sent to 2014 by Zachariah to see what would happen "if he still said no". Also 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".
- Henry can tap his own soul for power, something previously thought to be unique to angels.
- It is odd Dean held anger towards Henry about his "abandonment" of John, since it was not in Henry's control. In fact, Dean stopped him from returning to the past to set things right.
- Henry's tactic of carving Devil's Traps into bullets would become a recurring element in season 9 and 10.
- Henry is the only one of Sam and Dean's grandfathers not to be an antagonist.
- Unlike Samuel Campbell, Henry was killed in his introduction and did not live very long in the future.
- Henry was not informed of his third grandson Adam Milligan.
- Cuthbert Sinclair suggests that despite his mannerisms when Sam and Dean encounter him, believing whole-heartedly in the Men of Letters cause to the point of putting it above his family, Henry was actually something of a rebel. Cuthbert tells them that even though he had been kicked out of the order, Henry would still visit him in secret.
- Unlike his son and grandsons, Henry was never resurrected.
- This makes him the first Winchester to have one permanent death.
- As Henry is a descendant of Cain and Abel, he can most likely be possessed by Michael.
- According to Adam Glass, there was a scene cut that featured Henry telling Sam he saw more of John in Sam than he saw in Dean.