In a specific sense, Dean greatly fears losing individuals in his life, from John to Sam to Cas to Bobby. Even in a general sense, though, Dean is consistently shown not to want to be alone, to be scared of getting abandoned.
I also outlined Dean's tragic flaw as the self-sacrifice maneuver typically triggered by the loss of family. Dean is primed to sacrifice himself to save Sammy at any cost.
Episode 8: “The Scorpion and the Frog”
Nobody was prepared to see big, brave Dean Winchester afraid of spiders!
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. He also had several psionic abilities, the most notable of which is being able to summon and call the First Blade to him granted it is reasonable range.
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.
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. No matter if it's a fistfight, a weapons-laden war or simply leveraging his weaknesses against an opponent's, Dean is the better brother.
Lucifer is the most recurring Big Bad in the series. Naomi, The Darkness and God are the only antagonists not to have been killed. The Mark of Cain is the only Big Bad that is not a living being.
Burgers. Dean Winchester survives on burgers, so if you want to pay homage to the hell-and-purgatory-surviving Winchester, you could stop by at any old burger joint and order the biggest burger they have. But we've found one burger that Dean would definitely love and we have to share it with you.
That evening, Dean's strange behavior escalates and he sets off an EMF detector, proving that he's "haunted." He's also begun to incessantly scratch his left forearm. A call to Bobby diagnoses Ghost sickness, in which a spirit literally infects a person with fear, which intensifies until the victim's heart gives out.
While conversing with the Black Horseman, Dean is told by Famine that he is empty inside which is the reason why he remains unaffected by his influence, Famine mocks him for this. Sam arrives and Famine tries to compel him to drink the blood of his demons, but Sam manages to refuse.
2.20 What Is and What Should Never Be
Dean visits John's gravesite and talks to him, asking why he always has to be the hero and save the people. Being tired of always being the one to sacrifice something leads to Dean shedding a tear.
When Dean Winchester is sent to Hell at the end of the third season, it is the demon Alastair who tortures him, stopping only when he eventually convinces Dean to torture other souls himself.
Afterwards, Dean has shown that he has moved past his depression as he tried to comfort Sam over his own anger at the loss of both Mary and Jack. However, some of Dean's anger remained as he was still upset God didn't intervene even voicing the latter didn't care at all.
“Shadow” (1x16): One of the most violent episodes of Supernatural overall, we think. Literally everybody got their butts kicked and lost blood at some point in this one. Daevas are clearly nothing to mess with, not to mention Meg, who got her own temporary comeuppance during this episode.
Weakest: ASMODEUS
Not only did his plan of taking over Hell fail, but he also then tried to take on Gabriel. This was a huge mistake, and when he fell, it caused the extinction of the Princes of Hell. Asmodeus never matched up to any of the denizens of Hell that appeared on Supernatural before him.
Whether Dean (Jensen Ackles) is your No. 1 man or Sam (Jared Padalecki) is the one who makes your heart go pitter patter, one thing is for sure: No one is hotter than the Winchester brothers!
Strongest: Eliot Ness
According to the Supernatural mythos, sometime during the 1940s, he learned about the existence of supernatural creatures, later becoming a hunter himself. Although details of Ness's past hunts aren't given, it is known that he was responsible for taking out a nest of vampires near Cleveland.
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.
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.
Sam loses his demon powers, claiming that the force that transported him and Dean onto the plane cleaned him up.