|“||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 is a character appearing in CW's Supernatural. He is a member of a secret society known for their knowledge of the supernatural world called Men of Letters. He is the father of John Winchester and the paternal grandfather of Sam and Dean Winchester as well as Adam Millagan. He is portrayed by Gil McKinney.
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. Henry then attempts to exorcise the leader, a powerful demon known as a Knight of Hell named Abaddon, she proves immune and knocks him out. She then 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 fooled Henry. It works and Henry leaves with Abaddon none the wiser, not knowing that Josie was possessed by her. However, the experience causes him to change his mind about leaving the order as they saved people's lives through their efforts.
Henry is seen greeting his son, John goodnight, telling him that he's 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 which was a legacy in their family.
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 to right his wrong towards his son. Dean disagrees and forces him not to go through with it as it may jeopardize his and Sam's existence. Through this Dean realizes his error in treating his grandfather, he forgives Henry as he sees it wasn't his fault in leaving his father.
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.
Dean and Sam later bury Henry in a cemetery with other fallen Men of Letters.
When John was transported from 2003 to present day and reunited with his sons, he discovered the truth about Henry and that he didn't abandon him on purpose.