Henry Winchester was the father of John Winchester, and the paternal grandfather of Sam and Dean, and was a Man of Letters. Henry was forced to time travel from 1958 to 2013 to escape Abaddon, unintentionally leaving his son estranged to grow up fatherless and become a hunter over the years between, and Henry was subsequently killed in 2013 when fighting Abaddon with his grandsons.
Henry Winchester was presumably born sometime in the early 20th century. Henry was the latest in a long paternal bloodline of Men of Letters, and thus was himself by bloodline a legacy who was to be ordained into the Men of Letters. (As Time Goes By) At some point in his life, Henry apparently married a woman named Millie, (Mother's Little Helper) and they had a son, John Winchester, in 1954. While John was too young to know of the Men of Letters, (As Time Goes By) it was implied that Millie knew. (Mother's Little Helper)
In his adulthood, Henry, alongside Josie Sands, began undergoing the rites and assignments to be initiated into the Men of Letters. (As Time Goes By, Mother's Little Helper) Among the Men of Letters, Henry's mentor was Cuthbert Sinclair, until the latter was kicked out of the order in 1956. However, even after Sinclair was removed from the Men of Letters, Henry would still secretly visit him at his supernaturally-hidden mansion. (Blade Runners)
In August, 1958, Henry and Josie, as their final assignment by the Men of Letters before being initiated, were sent by the order to St. Bonaventure Convent, posing as Inquisition officers of the Vatican, to investigate a possible demonic possession case there (where one of the nuns had seemingly gone insane, killing two others and committing suicide). When Henry and Josie were shown the scrawlings the nun had carved and written in blood on her bedroom wall, Josie identified a crest among the scrawlings as referring to the Knights of Hell.
Henry and Josie eventually discovered that several of the local nuns were possessed by demons, and found and exorcised the demons just as they were about to extract Sister Julia Wilkinson's soul. However, one of the last remaining demons, actually Abaddon unbeknownst to Henry, was able to knock Henry out due to being unaffected by the exorcism rites as a Knight of Hell. When Henry awoke, it seemed to him that this case was a minor demon infestation and that he and Josie had exorcised all the demons, and so Henry and Josie left the next day; but in actuality, Josie was now possessed by Abaddon so that Abaddon could infiltrate and destroy the Men of Letters. (Mother's Little Helper)
Meeting his grandsonsEdit
On 12 August, 1958, the night of Henry and Josie's final initiation into the Men of Letters by the order's elders, the elders' residence at 242 Gaines Street in Normal, Illinois was attacked and massacred by Abaddon. A blinded Larry Ganem entrusted Henry with a box containing the key that Abaddon was after, prompting Abaddon to pursue Henry after killing the elders. In order to escape from Abaddon to safety and protect the key, Henry performed a time travel blood spell, intended to transport him through time to his next of kin in the future, which propelled him through time to 2013.
Upon arriving in 2013, Henry had expected the spell to transport him to his son John's adult self, but it instead transported Henry to John's sons and Henry's future grandsons, Sam and Dean. Before Henry could go anywhere, Abaddon followed him to 2013 through the blood spell, forcing Henry, Sam and Dean to flee in the Impala. Henry was overwhelmed to discover that Sam and Dean were his future grandsons and that John was dead in 2013, and was surprised and semi-disappointed that John had never been initiated as a Man of Letters and had raised Sam and Dean to be hunters. Henry soon learned that the reason for this was that after the Men of Letters had been massacred by Abaddon in 1958 before their time jump, the order had apparently become extinct and been forgotten.
In hopes of finding answers about the key Ganem had entrusted Henry with, the three Winchesters searched for any clue to indicate that one of the elders may have survived Abaddon's massacre. Henry was led to a possible clue when he found someone had planted Albert Magnus - the Men of Letters' alias used when incognito - into the list of deaths, and at the cemetery where all the deceased elders were buried, Henry and his grandsons discovered that Larry Ganem was probably still alive when they found that Ganem's grave instead held someone else's corpse.
Over the following night, while Sam's research produced indications that Larry Ganem had indeed survived and swapped identities with the corpse in his grave, Henry, upon seeing John's hunter journal and recognising it as his own new one in 1958, learned that in this future world, he never made it back to 1958 and thus John grew up without him and never saw him again. This greatly upset Henry, and Henry's anguish with himself over John growing up without him only intensified greatly when Henry read John's journal and learned from it just how harsh and brutal John's life had been in Henry's absence. In an act of emotional anguish, Henry snuck out while Sam and Dean were asleep, with the intentions of gathering the time spell's ingredients so he could repeat and return to his time and try to change the course of John's life. After Henry had gathered all the ingredients (one from the Impala's trunk and the others from a local hoodoo shop), he was found and stopped by Dean before he could perform the time spell, due to the heavy risk of changing the past. (As Time Goes By)
Defeating Abaddon and deathEdit
After Dean stopped Henry from returning to 1958 and changing the past, Abaddon, having captured Sam, demanded a hostage exchange - Sam and his life for Henry and the key. Though Dean pretended to comply with Abaddon's demands and take Henry captive for the exchange, in actuality, Dean and Henry had come up with a secret plan to double-cross and stop Abaddon - once Sam and Henry were exchanged, Henry would get close enough to Abaddon to fire a bullet engraved with a devil's trap into Abaddon's skull, so that the trap's effects would bind and incapacitate Abaddon. Henry and Dean pulled off their backup plan when Abaddon double-crossed them, and succeeded in immobilising and stopping Abaddon, but not before she mortally wounded Henry by stabbing him in the belly.
Henry subsequently died in his grandsons' arms, but not before telling them with his dying breaths that they were indeed true Winchesters, and that Henry knew after meeting them that he would have been proud of the man John grew up to be. Sam and Dean afterwards buried Henry at the cemetery among the deceased Men of Letters. (As Time Goes By)
Henry Winchester was an awkward and impatient but very intelligent, loyal and loving man. He was calculating, and tended to view and think of the bigger picture more so than the smaller things around him that he considered 'petty' or 'irrelevant,' due to which he could sometimes be uptight, contemptuous and impatient towards others, mainly when said others failed to see like him that time was quickly running out. Henry also, as a Man of Letters, had the order's traditional-mindset view of hunters as rash-headed lowlifes and beneath him, and had a tendency towards judging aggression from strangers as a sign of low intelligence, but Henry proved in his last moments that he is not fully biased against hunters. Henry was also admittedly unused to being part of action in the field, as he was more used to research and bookwork. Despite possessing a few of the Men of Letters' traditionalist views, Henry was nevertheless a very cunning and independent individual, who was able to think on his feet and calculate ways of evading the enemy very quickly.
While Henry did not see eye-to-eye with his future hunter grandsons, he was nevertheless a very brave and loyal man for his family, and a true Winchester like John, Sam and Dean grew up to be. Henry's love for and loyalty to his family was, at very emotional times for him, able to override his logic and push him to attempt extremely radical and risky courses of action. (i.e., the discovery of how hard John's life was in his absence drove Henry to attempt to go back to his time and alter the past, despite the massive risks and consequences of altering history.) Henry was also able to work much better with others in saving his family or kin when they were in danger, and was perfectly willing to risk or even sacrifice his own life for his family or for others he cared about. What Henry lacked in strength and experience, he made up for with great cunning, scheming and resourcefulness; able to outwit, second-guess, mislead and even outplay and defeat intelligent and deadly foes such as Abaddon through quick thinking and planning ahead.
As a Man of Letters, Henry possessed vast and extensive knowledge of the supernatural world and knew secrets usually unknown to even the most experienced hunters. Henry knew of the legends of the Knights of Hell, of the demon-killing knives of the Kurds, and of the time travel blood spell and all its ingredients (although according to Abaddon while possessing Josie, Henry still wasn't very skilled with spells by Men-of-Letters standards). Henry was also able to perform handcuff escapology, with which to escape handcuffs and slip them onto his captors' wrists while being cuffed. As a Man of Letters, Henry also knew how to harness the power of his own soul for spells.