- “My name is Dean Winchester. I'm an Aquarius. I enjoy sunsets, long walks on the beach, and frisky women. And I did not kill anyone.”
- —Dean Winchester
Dean Winchester was born on January 24, 1979 in Lawrence, Kansas to John and Mary Winchester. He is Sam Winchester's older brother by four years. Following the murder of Mary Winchester by the demon Azaezel on November 2, 1983, John handed over the responsibility of raising Sam, who was six months old at the time, to Dean. This protectiveness has lasted their entire lives, and has been the cause of many arguments between the Winchester boys.
As John begins to investigate Mary's death and subsequently learns about the supernatural beings in the world, he begins to hunt them. As a result, Dean and Sam are hunters from a young age. The Winchester constantly moved around the country, living in motels and houses of other hunters. When Dean was 16, he was arrested for stealing food while John was away on a hunting trip and spent time in a boy's home where he had the chance to go to a regular school, but ultimately gave it up due to return to John and, more importantly, Sam. Dean is known for being able to handle a large amount of weaponry. He is commonly seen in a dark leather jacket, dark shirts, and dark jeans. He is also known to drive a black 1967 Chevrolet Impala Sport Coupe, which he keeps a stash of hunting paraphernalia hidden in the trunk.
- Abbadean – the ship between Dean and Abaddon
- Chestervelle – the ship between Dean and Jo
- Deanna – the ship between Dean and Anna
- Dela — the ship between Dean and Bela
- Demara — the ship between Dean and Amara
- Duby — the ship between Dean and Ruby
- Winchambers – the ship between Dean and Krissy
- Balthean – the ship between Dean and Balthazar
- Debriel – the ship between Dean and Gabriel
- Denny – the ship between Dean and Benny
- Destiel – the ship between Dean and Castiel
- Drowley – the ship between Dean and Crowley
- Ducifer – the ship between Dean and Lucifer
- Michean – the ship between Dean and Michael
- Weecest – the ship between young!Dean and young!Sam
- Wincest – the ship between Dean and Sam
- Deanpala – the ship between Dean and the Impala
- Main article: Deanna
- Main article: Destiel
- Main article: Wincest
- "House rules, Sammy: Driver picks the music, shotgun shuts his cake hole."
- I'm not gonna die in a hospital where the nurses aren't even hot."
- "I like him, he says 'okie-dokie'."
5.01 Sympathy for the Devil
- "Oh yeah, life as an angel condom. That's real fun."
5.22 Swan Song
- "Sam, it's okay. It's okay, I'm here. I'm here, I'm not gonna leave you. I'm not gonna leave you."
6.09 Clap Your Hands If You Believe