‘Supernatural’: 13 Most Loyal Members of Team Winchester

Supernatural Mary Winchester Bobby Singer Charlie Bradbury
Diyah Pera/The CW; Liane Hentscher/©The CW/courtesy Everett Collection; The CW

Hey, SPN Family! This is an excerpt from TV Guide Magazine’s special issue, Supernatural Forever! Grab it on newsstands now through August 16, 2021 for a ton of incredible pics of the boys, a pull-out poster and the full scoop on all 15 seasons of the demon-hunting hit!

Over 15 seasons of Supernatural, the Winchester family evolved into a core four: demon-hunting siblings Dean (Jensen Ackles) and Sam (Jared Padalecki) Winchester, angel Castiel (Misha Collins) and Jack (Alexander Calvert), the son of Lucifer (Mark Pellegrino) and human Kelly Kline (Courtney Ford), making him a Nephilim (Jack later evolved into God).

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Take a walk down memory lane with these heavenly and hellish characters.

But as powerful as the quartet were, they couldn’t have vanquished rogue angels, demons and other monsters without allies willing to sacrifice everything for Team Winchester.

Here is a dossier on a baker’s dozen of those who helped the show’s heroes in their fight for good.

Liane Hentscher / ©The CW / Courtesy: Everett Collection

Benny Lafitte

Who is he? A vampire (Ty Olsson) trying to be ethical.

How he helped In Purgatory after his vampire maker decapitated him, the ex-pirate saved new arrival Dean from a monster, then showed him the way out once Dean agreed to let his soul hitch a ride. On Earth, Dean resurrected Benny.

His hero moment Voluntarily back in Purgatory, Benny sacrificed himself to fellow bloodsuckers and rescued Sam and Bobby in an epic Season 8 scene.

Liane Hentscher/©The CW/courtesy Everett Collection

Bobby Singer

Who is he? The longtime Winchester family friend (Jim Beaver, above center) was a hunter, keeper of supernatural lore, vengeful spirit and, most of all, father figure to Sam and Dean.

How he helped Telling the boys, “Family don’t end with blood,” he supported them — even when soulless Sam tried to kill him — until he was shot by the cannibalistic Leviathan Dick Roman (James Patrick Stuart). And from Heaven, he kept trying to help his beloved “idjits.”

His hero moment When he attacked Dean while demonically possessed in Season 5, Bobby took back control long enough to stab himself with a demon-killing knife. The monster inside died, but Bobby was paralyzed until he made a deal with future King of Hell Crowley (Mark A. Sheppard).

Diyah Pera/The CW

Rowena Macleod

Who is she? A powerful, cunning and oft-diabolical 17th-century Scottish witch and, later, Queen of Hell (Ruth Connell). She’s also the mother of Crowley, who resented her for abandoning him as a human child.

How she helped Although originally the Winchesters’ immortal enemy, Rowena often answered their call for her magical help…if she saw some personal benefit. Based on their mutual suffering at the hands of Lucifer, she bonded with Sam and — seeking redemption for such sins as sending her time-traveling grandson to a certain death — decided to work for the boys’ Team Free Will.

Her hero moment In Season 15, as Hell’s ghosts were unleashed on Earth, Rowena sacrificed her own life to save the world by using a spell and casting the evildoers back into the Underworld.

Diyah Pera/The CW

Mary Winchester

Who is she? Sam and Dean’s mom (Samantha Smith).

How she helped Though she was killed by the demon Azazel (Fredric Lehne) when she unsuccessfully tried to stop him from feeding his blood to the infant Sam, Mary was resurrected 33 years later by God’s sister Amara (Emily Swallow), as a gesture of gratitude to Dean. Raised in a hunter family, the Winchester matriarch became an effective ally to her sons as well as a fervid protector of them.

Her hero moment In Season 12, when the birth of Lucifer’s son Jack opened a rift into Apocalypse World, Mary pushed Lucifer through the portal and out of the main world, but not before he pulled her in as well. In the other universe, she kept fighting for humans she met.

Bettina Strauss / © The CW / Courtesy Everett Collection

Garth Fitzgerald IV

Who is he? A hunter, werewolf, werewolf dentist and family man (DJ Qualls, far left).

How he helped Though not the best monster killer — the kindly soul got beaten up a lot — he took over the late Bobby’s job helping answer hunters’ questions.

His hero moment After he turned into a werewolf, he got stronger (but not mean!) and saved the Winchesters from a monster fight club in Season 15. For the first time, they called Garth the hero of the story.

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Pamela Barnes

Who is she? A benevolent psychic (Thunderbird Dinwiddie, far right) blinded by Castiel.

How she helped Her gift guided hunters — Sam and Dean included — to reapers.

Her hero moment After she projected the brothers into the astral plane in Season 4, demons attacked her while she was guarding the guys’ vacant bodies. Mortally wounded, Pamela managed to return the two to their own forms.

Bettina Strauss/The CW

Sheriff Jody Mills

Who is she? A principled and savvy law enforcer turned hunter (Kim Rhodes, near left). The loving adoptive mom to a batch of once-troubled girls — Padalecki describes Jody’s character as “really cool” — inspired a spin­off (that wasn’t picked up to series).

How she helped After Sam, Dean and Bobby saved her town from zombies (including her back-from-the-dead young son), Jody slowly got involved in the monster-killing business.

Her hero moment The sheriff showed off her impressive skills during an assault on the compound of the heavily armed British Men of Letters. In the Season 12 sequence, she shot powerful leader Dr. Hess (Gillian Barber), nullifying the group’s threat to exterminate all American demon hunters!

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Claire Novak

Who is she? One of Jody’s adopted runaway girls. The zealous hunter’s late father was Jimmy Novak, a devout man who had agreed to be Castiel’s human vessel.

How she helped Claire (Kathryn Newton) lived to kill monsters and fought alongside the show’s good guys on many cases.

Her hero moment After losing her mom to a rogue angel who was about to kill Castiel, she slayed the being with his own sword and saved Cass in a tense scene from Season 10.

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Charlie Bradbury

Who is she? The computer hacker and devoted cosplayer (Felicia Day) had a (platonic) fondness for Dean.

How she helped The Winchesters relied on the self-described nerd’s hacking skills to solve several cases.

Her hero moment Hunted by the monstrous Styne family, who wanted the Book of the Damned back, Charlie was determined to translate it and help free Dean from the evil-causing Mark of Cain in Season 10. She died, but later the Apocalypse World’s Charlie, a seasoned hunter, joined the bros in the bunker.

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Sheriff Donna Hanscum

Who is she? A Minnesota law enforcement officer and happy hunter played by Brianna Buckmaster.

How she helped When fellow cop Jody looped her into the monster menace, the once-skeptical Donna became a champion vampire slayer in her own right.

Her hero moment In her first supernatural confrontation back in Season 10, Donna killed a vampire who was about to feast on Jody. Not bad for a newbie!

David Gray / © THE CW / courtesy everett collection

Ellen and Jo Harvelle

Who are they? A fierce mother-daughter hunting duo.

How they helped Ellen (Samantha Ferris, far left) and her child Jo (Alona Tal, near left) ran the hunters’ hangout, Harvelle’s Roadhouse. Though Ellen wanted to shield Jo from hunting (Jo’s dad died on a mission), they eventually would stalk monsters together. Out with the Winchesters, Jo once saved Dean after he was shot by a demon-possessed Sam.

Their hero moment On a mission in Season 5, Jo saved Dean again — this time from demon Meg’s (Rachel Miner) Hellhounds — but she was mauled. Holed up in a store, Jo told the brothers to build a bomb and then escape. Once they were gone, Jo died, and Mom blew up the demon dogs…and herself.

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Kevin Tran

Who is he? A brainy high school student, prophet and, following his death, a ghost.

How he helped After lightning struck him, Kevin (Osric Chau, near right) was able to translate the Word of God tablets. He was the only one who could read them, learning spells that returned celestials to Heaven and forced demons back to to Hell.

His hero moment In Season 8, while in captivity, he tricked Crowley by saying he could open a gate to Hell, but instead cast a spell that killed his demon guards. He escaped with a valuable tablet.