After a few years off the CW, the channel’s most enduring world of Supernatural has finally returned in the hit prequel series The Winchesters.

Executive produced by Dean Winchester himself, Jensen Ackles, The Winchesters tells the story of how Sam (Jared Padalecki) and Dean’s parents, John and Mary Winchester, first met and fell in love. Originally played by Jeffery Dean Morgan and Samantha Smith on Supernatural, and by Matt Cohen and Amy Gumenick as young adults in the “mothership” show’s time-travel episodes, John and Mary are played in this prequel series by Drake Rodger and Meg Donnelly as they search for their fathers in the paranormal world of the early 1970s.

Though Mary’s father, Samuel Colt (played originally by The X-Files alum Mitch Pileggi), is set to appear on the series later on this season, where he’ll be played by none other than Smallville star Tom Welling, John’s father is nowhere to be seen. Having disappeared years ago when John was still a child, Henry Winchester (Gil McKinney) was a Man of Letters, and one with a pretty good reason for missing his son’s entire life. Though John will no doubt continue to try and find his father on The Winchesters, longtime fans of Supernatural already have an answer for his father’s fate…

A Man of Letters
The Men of Letters were a paranormal secret society bent on containing and holding back the supernatural forces that threatened to destroy our world. For centuries, the Men of Letters made it their business to hold back the darkness of the mythical Akrida, beings from another dimension who could actually destroy the world. At every turn, the Men of Letters succeeded, and held the Akrida at bay. Each Man of Letters comes from a distinct bloodline, making their children Legacies. Henry Winchester was a Legacy himself, coming from a long line of Winchesters who joined the Men of Letters.

Aside from his studies, Henry was also tasked with some field work for the Men of Letters, who partnered him up with fellow initiate, Josie Sands. Josie loved Henry, but since he was faithfully married to his wife Millie (Bianca Kajlich) and had a son, she didn’t pursue him any further. In the Supernatural episode “Mother’s Little Helper,” Henry and Josie are sent to Milton, Illinois on assignment from their superiors where they investigated a case of demonic possession. While there, Henry lamented his assignment, wishing more than anything not to abandon his family.

On the case, Henry and Josie exorcise two of the three demons involved in the bizarre string of murders, but one of them — a Knight of Hell named Abaddon — knocks Henry out, with plans to use the Winchester to infiltrate and destroy the American branch of the Men of Letters. Due to her love for Henry, Josie is able to persuade Abaddon to take her instead and the demon leaves with Henry, posing as Josie as they head back home. Completely unsuspecting, Henry trusts the demon, unaware that his friend is all-but-dead and the evil spirit is wearing her like a puppet.

Initiation Gone Wrong
Not long after these events, Henry and the demon-possessed Josie attended their final initiation into the Men of Letters. The ceremony was held in Normal, Illinois, but contrary to the name of the location, it was anything but. It was this very night when Henry would say his final goodbye to his young son John, who was only 4 years old at the time. The young boy went to bed assuming that he would see his father the next day, but Henry slipped quietly out of the house, on his way to be sworn in as a full member of the Men of Letters.

Within the hour, Henry met Josie at an undisclosed location for the initiation ritual. What was meant to be a night of celebration and promise quickly turned into a horror show, which makes sense given that Supernatural was always best when it played up the horror. After the Elders took Josie behind closed doors, it wasn’t long before Henry heard screams coming from inside. What he saw was worse than he could’ve imagined, and was exactly the type of thing he was about to swear to try and prevent.

Breaking in, Henry encountered a dying Man of Letters who gave him a key to all the secret societies’ secrets, but not before noticing that Abaddon had killed everyone else inside. Fleeing for his life, Henry locked himself in an adjacent room and used a spell to open a portal. Without so much as an afterthought, only hoping that he would return to his son, Henry jumped right in. Though he didn’t know it at the time, Abaddon was not far behind and would follow him through time.

Time-Traveling to the Future
As chronicled in the Supernatural episode “As Time Goes By,” Henry arrives in the year 2013 after escaping Abaddon in 1958. Due to the nature of his spell, he was sent into the future to find his son, but since John had died in 2006, Henry was taken to his grandchildren, Sam and Dean Winchester, instead, which turns out to be both shocking and disappointing to him.

Because John grew up without Henry, he hated the man, and while we don’t know much about what his home life was like outside of being raised by his mother Millie, the Supernatural episode “In The Beginning” (which takes place in 1974) implies that he had some sort of father-figure who replaced Henry. Nevertheless, Henry learns from his grandchildren that John grew up to be a Hunter, which was unheard of for, and even disgusting to, a Man of Letters.

Because of their bloodline, Sam, Dean, and their father should’ve all been Men of Letters Legacies, but without Henry there to show them the way — and since the American branch of the Men of Letters was wiped out by Abaddon in 1958 — they knew nothing of the secret society. As Henry began to educate his grandsons, the Knight of Hell caught up with and killed Henry before Sam and Dean could send him back to the past to help raise their father. Dying in their arms, Henry admitted he was proud of them, stating that he didn’t know his own son as a man, but knowing them makes him proud of John anyway.

The Winchester Legacy
But Henry’s sacrifice wasn’t in vain. He passed the key to the Men of Letters’ secrets onto his grandchildren, who then found the Men of Letters bunker in Lebanon, Kansas, which wasn’t too far from their own hometown of Lawrence. With this new base of operations, Sam and Dean finally had a home, and they used the bunker’s vast resources to defeat countless global threats and kill plenty of monsters along the way. Henry may have lost his life, but his grandchildren benefited from his sacrifice. In fact, without access to the Men of Letters resources, Dean would’ve never killed Abaddon and avenged their grandfather’s death.

Years later, in Supernatural’s 300th episode “Lebanon,” Dean wishes their father from the year 2003 to the present time of 2019. After being reunited with his family, Sam and Dean explain to their father that Henry didn’t abandon him at all, but that he died protecting them and giving his grandchildren a fighting chance against the forces of evil. Finally understanding his father’s absence, John accepts that he and his sons are Men of Letters Legacies and seemingly forgives his father for “walking out on” the Winchester family.

While we don’t yet know how John’s discovery of his father’s role as a Man of Letters is going to affect him on The Winchesters, we do know that Henry Winchester didn’t want to abandon his family and that in the end, he was actually protecting them. Whether John and Millie will ever come to understand this on The Winchesters (which takes place in 1972) has yet to be seen, but we can rest assured in knowing that eventually, John will learn the truth, and even follow in his father’s footsteps by sacrificing his own life for the sake of his sons. Because, at the end of the day, the world of Supernatural and The Winchesters is all about family anyway.


By Damyan Ivanov

My name is Damyan Ivanov and i was born in 1998 in Varna, Bulgaria. Graduated high school in 2016 and since then i'm working on wordpress news websites.