Henry Winchester

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Henry Winchester
from Supernatural
Chroniclers of All Man Does Not Understand
Arrival Date: 1/1/17
Age: 34
Birthdate: 08 January 1924

Height: 6'
Weight: 170 lbs
Hair: Dark Brown
Eyes: Green
Build: Athletic verging on dad bod
Complexion: Pale
Accent: Midwestern

People of Note: n/a

[st_udious.dreamwidth.org ] - [henry+winchester ]
Player: Reg
Portrayed by
Gil McKinney

Theme Song:
"Track You Down"
by Sondre Lerche

Enthusiastic Little Rogue Wizard:
time to roll an arcana check

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.

A Brief Introduction

simply to whet the appetite

Henry Winchester carries himself with the casual sort of confidence and grace of a man who knows exactly what he's about. He walks a little straighter than most men, but he was taught to. Slouching was unacceptable behavior for any young man who wanted to make something of himself. Henry absolutely wanted to make something of himself. He's charismatic and approachable and for all the world can look into someone's eyes and make them feel like they're the only person in existence without the use of even a single sliver of magic. He's prone to singing absently and has a very pleasant voice, though he'll thank you not to say anything about it. He wears his emotions on his sleeve. Henry's always had a hard time concealing them unless he's playing a role or otherwise knows he's in a situation where it's essential.


a gentleman and a scholar

When one pictures a Winchester, they tend to imagine Henry's son or grandsons. Henry is not John and he most certainly is not Dean. What Henry is, by Winchester standards, is soft. He's warm hearted and kind. He has a hard time recognizing when someone is flirting with him or when they're just genuinely sincere and lovely people. Similarly, he'll often be flirting with people and have no earthly clue that he's doing it. He truly wants to believe the best of people. He knows better, of course. There are those who would take advantage of his good nature, of course. Everyone gets one chance. It is very much not a chance that should be wasted. Beyond that, Henry is clever and knows it. Sometimes it gets him into trouble. Alright, often it gets him into trouble. Occasionally, he has trouble prioritizing things and his head starts to hurt trying to keep track of what one part of him says is the most important and what the other does. This internal conflict looks a great deal like indigestion. He can be, from time to time, too stubborn and strong-willed for his own good and unwilling to see the flaws in those close to him. Cuthbert Sinclair, for example was...far less than sane and yet Henry still considered him a friend and still went to him to learn things that the order was hesitant to teach him. He then had to pretend not to know those things and it all got very messy in his head again.

Henry is stubborn and somewhat of an elitist, believing that regular people should not be exposed to the supernatural and that hunters are apes and brutes and not at all worth associating with though he is beginning to come around on that after time spent with his grandsons. He also places duty above all else, but his idea of what duty he’s adhering to can be inconsistent. In one moment it’s protecting the Men of Letters at all cost and the next it’s Family. Family is likely the more important one if Henry’s to be honest with himself, but he never got a chance to prove his mettle in WWII like many others his age did and so part of him still subscribes to the notion that instead of serving his country at obvious war, he was and continues to serve it in the supernatural one. This can also manifest itself in a great deal of guilt he refuses to speak of. Guilt that he was kept out of the War in Germany and guilt that his decision to protect everyone by fleeing Abbadon caused John to grow up in a much harder life than Henry ever would’ve wanted for him. He also, from time to time can be a bit of an absent minded professor. For example, knowing exactly how to execute the blood sigil to get away from Abbadon quickly and safely but forgetting to lock the door behind him so she couldn’t follow.

Before The Fall

a headcanon history of events prior to appearing in the show

Basic Early Life Things

  • Father - George Charles Winchester b. 1899 - 1957
  • Mother - Mary Rose Winchester (née Murphy) b. 1908 - 1930
  • Mother died in childbirth. Father never remarried.
  • Younger Sister - Eleanor Rose Winchester b. 1930 - 1935 (Illness)
  • After his mother died, the MoL stepped in to help the Winchesters and their new addition as much as possible though Henry wouldn’t know that until much later.
  • Spent the Depression doing what he could to ensure that things around the house got done and that there was food, which was not at all always easy and most definitely was not always legal. Tried to be noble about it when he stole, but he was young and sometimes he was merely justifying things to himself.
  • This laid the foundation for his sleight of hand and helped make misdirection and such things his best subject when he began his studies. Lore and symbolism were his second best. Spellcraft was somewhere in the middle along with a few other things. Combat was at the very bottom. He’s more the type to charm himself out of a situation than have things come to blows.
  • Began Men of Letters training officially at 13
  • Father began easing him into it at 10 after several small tests to ensure that Henry was indeed the type of boy who didn’t run at the mouth.
  • Henry always took his MoL training very, very seriously.
  • Was very close friends with Josie Sands beginning at around this time, and only ever thought of her as the sibling he never had since they were going through so much together that they couldn’t talk to very many other people about.
  • Did very, very well in school.
  • Attended private all boys’ schools after elementary.
  • Had a few homosexual encounters in his youth and never thought anything of it since it was fairly common both at the schools and throughout history. Very progressive in that sense. Would identify as bisexual if the term existed, probably will as soon as it’s introduced to him.
  • Did not participate in team sports competitively, but loves baseball. It just wasn’t a priority and he very much dedicated himself to academic pursuits instead of athletic ones.
  • Went to Dominican University, graduated in 3 years so he could return home.
  • Chosen due to proximity to Chicago and one of the few schools in the area that had professorial staff already initiated into the MoL so that Henry could be kept an eye on and quietly continue his studies there.
  • Studied Classics and Accounting at the time, literate (and as fluent as possible) in Ancient Greek, Latin, Hebrew and Aramaic. His studies with the MoL also leave him with a rather expansive knowledge of Enochian though he'd never claim to be anything approaching fluent in that.
  • Upon graduation, returned home to Normal and was a freshly minted loan officer at Old National bank in Bloomington.
  • Was specifically forbidden by the MoL to join up with the war effort despite turning 18 not long at all after Pearl Harbor. Was very conflicted about this since part of him desperately wanted to help fight tyranny in all forms, but knew he had no place in battle.
  • Forced to register for selective service on 21st birthday in 1945, never called up. Unsure if this was purely luck or if the MoL had a hand in it.
  • Slightly bitter that he never served and couldn’t form a connection with men his own age based on that. His double life already made it difficult for him. Full of war stories he could never talk about.

Marriage and Pre-Fatherhood

  • Married Mildred Jean Thompson (Mille, b. 1926) spring of 1946
  • Met when she was working at a diner in Bloomington, IL summer of 1944
  • Thought she was the most beautiful person he’d ever seen
  • She had auburn hair and bright blue eyes and a smile he swore could light up a room.
  • Too scared to ask her out at first
  • Turns out she was dating a soldier anyway
  • Went to the diner once a week to get to know her
  • Soldier got jealous and possessive and tried to pick a fight with Henry
  • Strike that, successfully picked a fight with Henry...sort of, Henry didn’t do much fighting in the moment since he truly does not at all care for violence, got his ass thoroughly handed to him.
  • Fight was the impetus for Mille to leave soldier (Franklin, we’ll call him.)
  • Began properly courting her October 1944
  • Proposed Christmas Eve 1945
  • Marriage generally a very happy one.
  • Attempts to conceive plagued by miscarriages and one stillborn daughter
  • Had almost given up entirely, not wanting Millie to endure anymore pain and heartbreak.
  • Were looking into adoption when John was conceived, remained minorly hopeful after so much pain but kept doing research because he wanted to make sure they had a plan in place just in case this pregnancy ended like all the rest.
  • Complications during birth nearly killed Mille, but both she and John survived though in no small part to some desperate spellwork on Henry’s part.
  • By the time John was born, Henry had been promoted to Financial Manager at the bank
  • Owned a small, two story brownstone, very nice, lovely home.
  • Occasionally went out to do basic field research jobs for the MoL, but generally just kept up with his love of study and the work and managed somehow to maintain a balance between work, the MoL and his family.
  • Has a very basic knowledge of cooking and cleaning, quite enjoys the former when he has an excuse to since it lets him get very precise with things, loves precision and mathematics and logical creative thinking. His aunt taught him some domestic skills, but for the most part it simply wasn’t knowledge he was encouraged to learn and he was already encouraged and required to learn a great deal.

John’s Birth and After

  • Managed to get enough time off at the bank to be able to tend to his newborn and his ill wife for a couple weeks, though had to hire someone in to help after that since while he was very good at saving money, he needed to ensure that he still had a job so he could continue to provide for his family. Asking for help was a huge blow to his pride as a father and a husband, and he very much vowed to learn as many other pieces of arcane knowledge and healing magics in order to keep anything from happening to either of them ever again. Did not like feeling helpless through the whole process.
  • Millie had a partial hysterectomy a few months after John’s birth following long late discussions. Henry didn’t ever want to risk losing her again and never ever wanted her to suffer that pain again. They were well off enough that if they truly felt they wanted a second child, they could follow through with all of Henry’s research and adopt one.
  • John and Millie were his treasures. He loved them absolutely and unconditionally. He tells himself that he would’ve loved any child they brought into their family like that and likely he would, but there was something special about looking down at that little boy who had his eyes and his mother’s kind heart.
  • Very much enjoyed being a dad. Took his boy to the drive in. Allowed him to be young and afraid if he felt he had to, would be patient and kind with him, sing for him often, did his best to be a support and a comfort and everything he thought a good dad should be.
  • Took Millie out dancing as often as he could. Very much loved dancing with his wife and hoped they might one day teach their son properly, though he enjoyed doing what little uncomplicated steps his boy could manage, content to just let him flail and stomp around as long as he was laughing. Not many super family friendly places for dancing, but there were some Polish supper clubs that had polka nights that weren’t too late for young John that he swore his charming little boy enjoyed.
  • Took John to baseball games when he could too, usually minor league things. He had a plan that when his son was 10 he was going to take him to a Sox game like his dad used to.
  • Had just begun starting to teach John how to play the summer he got time displaced. Though she’d never admit it in polite company, Millie was far better at baseball than Henry ever was. He made sure to save properly and get time off so they could make a trip up to the city once a year before John was born to go to a baseball game. She was a Cubs fan. Somehow, there was peace in the house regardless.
  • Owned a television, but primarily only used it for watching the news, much preferred radio dramas and the like to television programs. The Shadow and Fibber McGee and Molly were his favorites while they were on the air.
  • The Adventures of Superman very much appealed to him as well as far as leisure television serials went.
  • Millie was quite fond of I Love Lucy and they both watched The Ed Sullivan Show together on a regular basis, making the program a kind of family affair. He truly enjoyed Dragnet though he tried not to watch it when John was awake. Things like Amos and Andy, I’ve Got A Secret, You Bet Your Life, The Adventures of Rin Tin Tin, Gang Busters, Captain Kangaroo (for John of course,) Ozzie and Harriet, Jack Benny, and The Honeymooners all also made it into occasional rotation in the household.
  • Henry was not directly involved in the beginnings of Civil Rights movement, but he did support it and generally went out of his way to be as decent and fair as he could to those who weren’t like him often limited by the bureaucracy involved in things to do much, but he tried. He held himself back from properly participating in order to do his level best to ensure that nothing put his family more at risk than they already were. He told himself it wasn’t his fight, that his fight was much different than that one and if he spread himself too thin there wasn’t going to be much point in fighting for Civil Rights because the true evils in the world might win.
  • Equally, he was terrified that his progressive leanings and egalitarian views would lead to him being branded a Red and having to deal with that. Though he did do the math one night and based on the information he had, he was pretty sure Normal-Bloomington was unlikely to be targeted, though if something large enough hit Springfield, they could be in quite a bit of danger. Still, he rationalized that the most likely target was Chicago. They were far enough away from there to be fine and he was sure any fallout from a surface detonation was likely to head east and perhaps north and not south west. He thought. Maybe. It was a very real possibility he was wrong since he had no idea how complete his information was. Either way, he loved Millie with all of his heart and refused to put them at more risk of being without him after they’d been through so much and worked so hard to have the family they did.
  • Clearly this didn’t work out.
  • He’d probably understand John a great deal more than he’d ever want to admit if he met him as a man. He certainly wouldn’t’ve parented the way John did, but John too knew the importance of Duty and Family.
  • He will never forgive himself for abandoning his wife and child, and that it was plausible to both Millie and John that Henry would just walk out on them tears him apart. He would never. Absolutely not.
  • He tries not to think about that too much.
  • He almost wishes that he'd followed his gut during his final trial and abandoned the order entirely instead of being convinced to stay on the grounds that they were helping people. Almost.

Time Traveling Through Motel Room Closets

what happened when he met the boys

This Is What We've Come To

a general chronicle of events since arriving at the Madonna