|“||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.||”|
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.
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.
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, 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.
- 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.
- 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 which indicates that Henry was not supposed to see Cuthbert at all and went against the rules to do so.