Supernatural: Dean Winchester’s 14 Biggest Fears, Ranked

Dean Winchester carries so much depth in his personality. He is the angrier and tougher of the two Winchester brothers in Supernatural, but the truth is that he carries a lot of weight on his shoulders that isn’t easily apparent at first.

Dean had certain things that he feared, to the point where they affected his personality. Some are easy to rationalize since most of the things he was scared of had to do with traumatic events or emotional aspects he didn’t know how to deal with. It’s worth taking a deeper look into them as they reveal a lot of layers to Jensen Ackles’ most famous role.

Updated on November 28th by Rhys McGinley:

With The Winchesters, fans are not only rejoicing in new Supernatural-based content but new Dean Winchester content, with the older Winchester brother being sorely missed in the week-to-week lives of the dedicated fandom since the show’s end. There is nothing new from Dean on an emotional level in the show, meaning his deep-rooted fears will not be delved into. While so often heroic and fearless, Dean gets scared of a variety of things in Supernatural, from things as simple as danger and monsters to deeper fears with more personal, emotional meaning.

14/14 Hellhounds

The first time Dean properly died in Supernatural, outside of Trickster interference, was at the end of season 3 when he is mauled by Hellhounds and sent to hell to suffer. It impacted Dean, to say the least, and he was never quite his typically confident self when dealing with the Hellhounds in the future.

It is hard to blame Dean for growing fearful, considering the way they tear his body apart. Dean would face a handful of Hellhounds after the fact, but he never quite settled around them and can be shown as visibly scared in his first couple of encounters with the dogs after escaping hell.

13/14 Harm Coming To Baby

There are few things as important to Dean Winchester as his car. Just about the only thing he cares more about than Baby is his family. So, it is understandable that Dean fears losing the ’67 Impala and even harm coming to it.

He tells Sam he would be reduced to murder should someone steal it and he always gets immensely upset when a monster/ghost/enemy touches the car. Dean and the Impala are an iconic duo, and while he may not fear losing it as much as he fears losing Sam or Cas, he still could not live without it.

12/14 Losing Mary Again & Disappointing Her

The return of Mary Winchester to Supernatural proved to be quite a waste. She did nothing in the show but tarnish her legacy to fans by being pretty unlikable. Dean loved her, though, and the thought of losing her again terrified him.

This can be seen clearly every time Mary leaves the Bunker or when her life is in danger – just look at how he broke down when she did pass. On top of fearing her second death, though, Dean always was conscious about letting her down. He idolized Mary, and the thought of disappointing her, and not being loved by her, broke him. His love for Mary is a personality trait he shares with John and with Sam, but neither of them quite shows their adoration like Dean does.

11/14 Being Abandoned & Alone

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.

There are various reasons for this, such as his deep-rooted self-loathing and immeasurable love for his family. No matter the reason, it is always hard seeing Dean have an emotional moment himself where the prospect of being alone gets too much.

10/14 His Fear Of Flying

Dean faced many powerful creatures in Supernatural, but he was never shown as outright scared as he was on an airplane. Perhaps this is only fear comparable to other people, as Dean did not like being trapped high up with no way out.

It can be linked to Dean’s hatred of not being in control, because getting stuck in a plane meant there was no way he could save himself in the event of a crash. He tried to overcome this fear in later seasons, although the general fear of planes remained.

9/14 The Prospect Of A Conventional Life

Dean may have settled into the “apple pie life” with Lisa, but he never liked it. He jumped on the first chance to return to hunting, mainly because domesticated life wasn’t something Dean ever envisioned or had a chance even to mull over when growing up.

It was shown that Dean was deeply unhappy to be out of action, so much so that the prospect of returning to such a life in later seasons would cause Dean great stress. Ultimately, Dean accepted his death when he admitted he was at least dying in the blaze of glory that had defined his life, which proved just how scared he was of a conventional lifestyle.

8/14 The Feeling Of Being Controlled

Dean became a different person in Supernatural’s final season due to fear, uncertainty, and rage. This stemmed from the revelation that Chuck had been pulling the strings of the Winchesters’ lives the whole time, which disturbed Dean more than Sam.

Dean was someone who always took charge and only needed to believe in himself that he could make things right. It’s why he was so afraid of the prospect of being stuck in an endless loop of Chuck’s challenges, as it meant that Dean could never control his destiny, as he had always believed.

7/14 Having To Face His Sorrows

Dean wasn’t just reluctant to talk about the heartbreaking tragedies that happened in Supernatural. He was outright afraid of facing them. Dean couldn’t handle the pain that came with reliving sad moments of the past, even if those things had happened not that long ago.

It’s why he was filled with such rage after Mary died, as he was scared of making himself feel the sorrow of her passing. Dean was shown weeping in private at one point, and appeared terrified of letting himself go there. As far as Dean was concerned, facing his inner pain was like fighting a monster that was out to kill him.

6/14 Letting His Father Down

Being completely loyal to John pretty much sums up Dean’s personality in Supernatural, at least where the first few seasons are concerned. Dean was like the perfect soldier regarding his father, having never questioned John and only ever wanting his approval.

It had the big side effect of making Dean scared of John’s disapproval, which saw him lose it several times. Dean was left clueless after John disappeared, and he even felt that he was somehow responsible for it. It speaks volumes for how shaken he was over disappointing John when he recalled decades-old instances that still haunted him for how his father reacted.

5/14 The Possibility Of Returning To Hell

Dean never wanted to go to Hell after he made the deal for Sam’s life, but he did put on a brave face. However, he couldn’t do so anymore following his resurrection, with Dean shown looking terrified at the mere mention of his time in Hell.

Considering he was relentlessly tortured for decades, it makes sense why Dean didn’t want to go back. Still, his fear was such that it was palpable for anyone who witnessed it, as Dean would retreat into his mind to unsuccessfully block out the torturous moments he had to endure.

4/14 Dissent In His Family

Dean would have no problem with admitting that Sam was likely John’s favorite son, even though Dean was the most dutiful. It’s because his greatest desire was for them to be together, and it never mattered to him if he had to sacrifice his life for it. While certain aspects of Dean have not aged well in Supernatural, his love for his family remains his strongest point.

Dean was shown to be extremely hurt by even the smallest sign of rejection from John, Sam, or Mary. In his final moments, he admitted to Sam that he was terrified he wouldn’t come with him to search for their father prior to the events of the first episode.

3/14 The Potential Return Of Azazel

Dean faced the most powerful beings in existence, including Lucifer, The Darkness, and God himself, yet his greatest supernatural fear remained Azazel. The terror stemmed from the traumatic childhood event when he lost his mother.

When he was poisoned by a Djinn, Dean’s fear manifested as an apparition of Azazel. It signified that he was still afraid of Azazel’s presence and was never convinced that he was free of the demon. Dean essentially associated Azazel with everything bad that happened in his life.

2/14 Not Being Able To Prevent The Death Of A Loved One

Dean was knee-deep in denial most of the time, claiming he and his friends could survive impossible odds. He convinced himself that he could save everyone, but this wasn’t always the case, and Dean’s worries came true for several characters, including Bobby, Castiel, Ellen, and Jo.

He refused to face this fear, even when it was obvious that he could do nothing about it, as seen during Castiel’s demise, where Dean kept imploring his friend not to sacrifice himself, despite there being no other option. For Dean, the death of a loved one was scary because he would then have to try and push down a whole new pain, along with so many others.

1/14 The Chance Of Losing Sam

There’s absolutely no doubt that this is the primary concern for Sam throughout the series. Dean would endure an eternity in Hell if it meant Sam was safe, and he could never live in a world that didn’t have his baby brother safe and sound.

Dean sacrificed his life, soul, livelihood, and whatever he could to keep Sam safe, even claiming that it was the entire purpose of his existence. Dean was glad he got to perish during his final death because he considered his life’s purpose complete when Sam agreed to let him go.

NEXT: 10 Supernatural Episodes Where The Winchesters Were Scarier Than The Monsters