Dean Winchester trumps
Dean Winchester - 100+ Times
His “permanent” deaths might be those which you could count, but Dean's actual number of deaths are impossible to calculate.
THE FINAL SCORE. Excluding the near misses and instances outside of the main timeline, Sam has died a total of eight times while Dean has died 112, if you include the 103 from the "Mystery Spot" episode. And you can bet, with the final season right around the corner, those scores will be going up one last time.
Meanwhile, Sammy has died just eight times (slacker!), but he does have the distinction of being the first brother to die, way back in Season 2. In honor of the show's final season, TVLine has compiled all of Dean and Sam's many, many death scenes, with details on how they died — and how they were brought back to life.
Power: Dean
Even if Sam is taller and generally seems more fit, Dean has demonstrated on many occasions that he's the more powerful of the Winchester brothers.
Dean: He's A Better Fighter
He's got a vast list of kills to his name, mainly due to his status as the better fighter between the brothers. Even in fights between the two, Dean has the upper hand in the number of wins.
Known as being empathetic, kind, and able to manipulate people via his famous puppy dog eyes, Sam Winchester is the smarter of the two Winchesters in terms of studies, even though he has refuted this fact.
Dean dies about 111 times in Supernatural. Most of those deaths can be attributed to the Trickster, who kills him about 103 times during season 3, episode 11, "Mystery Spot," when Dean and Sam are trapped in a time loop. Eleven of those deaths are seen onscreen.
Season Eight begins with Dean Winchester returning from purgatory, where he was sent after defeating the leader of the Leviathan – ancient monsters and first residents of purgatory. Dean spent a year in purgatory before being able to escape with the help of his vampire friend, Benny, whom he met in purgatory.
Emma Winchester is the daughter of Dean Winchester and Lydia.
After all, despite his intentions, Sam did the unthinkable. He betrayed him for a demon. Dean tried to see past it and focus on task but the hurt was too deep and the betrayal too raw. He couldn't forgive.
Eileen Leahy - Sam's final love (Season 15)
That is until Chuck wiped everyone from existence (“Despair”).
Dean is four years older than Sam and was always told from a young age to "watch out for Sammy". When a demon killed their mother, it was Dean who carried baby Sam out of the house. Dean was tasked as Sam's protector and, as a result, views himself as such.
Anyway, head to season 5 to see multiple heartbreaking Supernatural episodes. The first came with "Dark Side of the Moon." In this episode, the show ups the ante a bit when Sam and Dean both die. With both dead, the brothers can't really do anything to bring the other back.
Super Strength - When under the influence of the Mark of Cain or using its powers, Dean displayed superhuman strength at times. He was able to overpower and kill the vampire Connor and inflict pain upon the Grigori Tamiel when hitting him.
Regarding the time which purgatory lasts, the accepted opinion of R. Akiba is twelve months; according to R. Johanan b. Nuri, it is only forty-nine days.
Olsson first appeared on Supernatural in season 2 as a vampire named Eli but would later return to the show in season 8 as Benny, Dean's vampire bestie from his time in purgatory. He was last seen on the show in season 10.
Breaking the Seals
Dean is tortured in Hell. Dean Winchester spent four months in Earth time in Hell, but he stated that time passed differently there, and for him it was more like forty years. This made three days on Earth roughly equivalent to a year in Hell.
Before dying, John tells Dean, if he can't save Sam, he'll have to kill him, should he become evil. The fourth season episode "On the Head of a Pin" reveals that the demon Alastair tortured John in Hell for over a century, with John refusing the demon's offer to stop if he himself would torture someone else.
Dean Winchester (formerly) - As a Knight of Hell and with the Mark of Cain, he is virtually immortal. Unless he transfers the mark to someone else, and is killed by The First Blade, Dean will never die neither by natural or supernatural means.
As a human, Dean was the bearer of the Mark of Cain; this granted him extraordinary strength, allowing him to fight on the level of a supercharged angel like Metatron.
In compiling this list, I realized that despite Sam being the "sensitive" one, it is in fact Dean who cries the most tears throughout the series.
Due to his previous experience with Ruby, Sam did not trust Crowley at all and tried to kill him many times. He did not develop much trust in Crowley unlike Dean when the Winchesters first met him.