|Dates||???? – 2013 (killed by Abaddon)|
|Occupation||Men of Letters|
|Episode(s)|| 8.12 As Time Goes By|
9.17 Mother's Little Helper
You're more than that, actually. My father and his father before him were both Men of Letters, as John and you two should have been. We're preceptors, beholders, chroniclers of all that which man does not understand. We share our findings with a few trusted hunters – the very elite. They do the rest.
– Henry Winchester, 8.12 As Time Goes By
Henry Winchester is the father of John Winchester. Like his father and grandfather, he was a member of the secret society known as the Men of Letters. As far as John knew, Henry abandoned him when he was four. Henry was married to a woman named Millie, John's mother and Sam and Dean's grandmother.
Cuthbert Sinclair of the Men of Letters, was a mentor to Henry Winchester, teaching him how to use spells against his enemies. He was expelled from the Men of Letters in April 1956, despite this Henry would still visit Cuthbert at his hidden hideout.
Henry Winchester was due to be initiated into the Men of Letters in 1958, the night Abbadon massacred the order.
In 1958, Henry is seen greeting his son goodnight, telling him that he was leaving for work and that he will be back first thing in the morning. He then heads off and arrives at a door. He knocks on the door and is allowed to walk in. He sees Josie Sands in the hallway and they both are glad that they are being initiated after so long. A man calls out to Josie saying its time and Henry tells her good luck. He then hears screams in the room and bursts through. He notices Josie hanging one of the men up, and two other men bloody and dead on the floor. Larry Ganem, having being blinded by Josie, tells Henry that she is possessed by the demon named Abaddon. He then hands him a box and tells him to keep it safe and run. Henry escapes but not before being noticed by Abaddon. Henry goes into a room and starts to create a spell. He performs the spell and mysteriously pops out of Sam and Dean's hotel closet. Abaddon follows him and attacks Henry, Sam & Dean, who eventually escape.
Realizing that he's in the year 2013 and that Sam and Dean are his grandsons, he explains to them his situation and is shocked to find out that his son, John Winchester is dead. He also points out that he is saddened that his grandsons were raised as "hunters" and not one of the Men of Letters.
Learning that everything that has happened in the future has gone wrong, Henry tries to put everything right by attempting to use same spell to return to 1958, but is stopped by Dean as this would change the past. Although he is aware going back to put things right might alter the present, he 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 Key to the Bunker. 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, 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.
While tracking down former Man of Letters Magnus, Sam and Dean mention Henry to get Magnus' attention and he lets them in. He reveals himself to be Henry's former mentor and friend and claims that even after he was banished, Henry would still visit him in secret.
In 1958, shortly before their initiation, Henry and Josie Sands are sent on a field mission to investigate possible demonic possessions at a convent in Milton, Illinois. Henry poses as a priest, but expresses doubt to Josie about joining the Men of Letters as he fears dying and thus leaving his wife Millie and son John without him. Finding a symbol in the room where the dead nun slept, Henry is stunned when Josie identifies it as the crest of the Knights of Hell. That night, Henry and Josie burst into the basement where four possessed nuns are about to steal people's souls and Henry exorcises one while Josie exorcises another. When Henry tries to exorcise the leader, she proves immune and knocks him out. The demon reveals herself to be Abaddon and plans to possess Henry to investigate and infiltrate the Men of Letters. Josie offers herself instead and Abaddon possesses her, having the remaining demon pretend to be exorcised so she can claim they won and fool Henry. It works and Henry leaves with Abaddon none the wiser. However, the experience causes him to change his mind about leaving the order as they saved people's lives through their efforts.
In the present, Sam learns from Julia Wilkinson of Henry's visit and completes his and Josie's work in stopping the demons stealing souls.
Sam and Dean reveal to John how Henry time traveled to the future and helped them secure the Men of Letters Bunker, telling John that Henry would be real happy to see him sitting with them in the Bunker.