Jensen Ackles will return to the screen in a villainous role as Soldier Boy in Supernatural to be the actor’s apex role. The elder Winchester singling is the grittier of the pair of brothers, as Dean was always rough around the edges.
However, there were times when fans truly felt Dean’s plight, ranging from his grief at losing Sam to his suffering in places like Hell. There were also occasions where Dean could come across as an unlikeable protagonist. These range from his treatment of Castiel and Sam to questionable actions against innocent people. With Supernatural’s story done, it’s worth looking into when Dean was a hero whom fans felt bad for and when they had the opposite feelings for him.
Felt Bad For Dean
When Dean ed His Time In Hell
With Dean reluctant to share his memories of Hell with Sam after his resurrection and viewers encouraged to see things from Sam’s point of view, Dean came across as distant and unwelcoming. However, this perspective changed drastically when he finally told Sam all that happened.
Dean broke down in tears over his decision to torture people to end his own suffering, which clearly still gave him nightmares. Here, fans got to feel sorry for Dean for what he was keeping pent up inside of him as he felt shame for something he couldn’t control. It remains among the worst things that happened to Dean in Supernatural.
During Dean's Final Moments
Among the most Supernatural is Dean’s final speech to Sam. Before his last breath, Dean told his younger brother how much he ired him. He itted he didn’t see his death coming this way and wanted to look at Sam before he ed away.
Viewers understood why this was such a heartbreaking moment because all Dean had ever wanted was to spend his life with Sam without any worry. The pair had only just defeated Chuck but were now going to be separated. It was always so close yet so far for Dean and, once more, with cruel irony.
When Dean Traded His Soul For Sam
It was pretty clear that Dean’s reason for living was Sam when the latter was killed by Jake. Dean was so beside himself with grief that he took to talking to Sam’s corpse because he refused to truly believe his little brother was gone. Dean gradually lost his senses until he erupted in anger.
He ended up trading his soul to resurrect Sam and, even though it was the wrong decision, fans wouldn’t have been inclined to disagree with him. After all, watching him break down completely after Sam’s demise showed that Dean would rather be in Hell than live in a world that didn’t have Sam in it.
When Dean Lost His Memories
Dean was hit with a spell that slowly purged him of his memories, to the point where he can’t himself. The moment where this became horrifyingly clear was when Dean attempted to jog his memory by repeating the names of the people he loved while looking at himself in the mirror.
However, Dean lost his memory while this happened, culminating in him tearing up as his expression conveyed everything from terror to grief. It was a pitiful moment to watch since Dean was basically being erased from existence as his personality itself faded away.
When Dean Privately Wept Over Mary's Death
Dean became a real jerk after Jack accidentally caused Mary’s death, routinely taking out his anger on Castiel and Sam. Viewers got to see the side he was hiding at one point, though, which is where most would have forgotten their annoyance to feeling bad for him.
It turned out that Dean had been leaving the bunker to go deep into the woods just so he could have a place to cry. Here, Dean didn’t hold back on his tears and let his sorrow flow. The fact that he was all alone meant that this was the one place where he could stop pretending but with nobody there to console him.
Disliked Dean
Every Time Dean Punched Sam Out Of Anger
Certain things about have aged poorly, including his tendency to assault his brother. Dean knew Sam wasn’t going to hit his elder brother and took to punching him whenever he was angry at Sam - he even punched him when he was concerned.
On more than a few occasions, Sam would reveal a bleeding lip or a wound on his cheek, showing that Dean didn’t pull his punches either. Although they were used to getting beaten up due to the hunter lifestyle, it wasn’t fair of Dean to attack his younger sibling just because he either disagreed with him or wanted to vent his frustrations.
When Dean Blamed Castiel For Mary's Death
Among the Supernatural was to lay the blame for Mary’s death on Castiel. He regretted it later on after a long period of estrangement, during and prior to which he treated Castiel with venomous intent. Around this time, Dean would talk down to Castiel and give him the cold shoulder.
Dean even went so far as to send Castiel on dangerous missions against demons all by himself. Castiel has long been a fan favorite, so viewers weren’t going to share the same hatred Dean was exhibiting - it backfired on Dean himself, as the majority of fans were annoyed by his behavior.
When Dean Manipulated Sam To Trap Jack In The Ma'lak Box
Jack had given up his soul to save Dean and Sam’s lives from Michael, which was a kindness Dean didn’t care enough for. After Soulless Jack accidentally killed Mary, Dean wanted Jack dead - he ignored Sam and Castiel’s arguments over the fact that Jack couldn’t control his actions.
Dean then manipulated Sam into summoning Jack because the latter was close to Sam. His use of this tactic wasn’t well-received by fans since it twisted their former relationship. Dean got Sam to convince Jack into entering the Ma’lak box, which would have sealed him for eternity had Jack not broken out on his own.
When Dean Slew Sam's Friend In Front Of Her Son
Sam’s friend, Amy, was a Kitsune who had fed on innocent victims to save her son’s life. Sam gave her a for once rescuing him from Amy’s mother and asked Dean to let her go. The latter had pretended to agree, however, he eventually headed off to Amy’s to kill her.
After doing the deed, Dean realized Amy’s son was watching and initially threatened him when he suspected the child was a Kitsune. Dean ultimately left the kid with his dead mother, sarcastically telling the boy to track him down as an adult if he wanted revenge. This betrayal of Sam’s trust and stone-cold treatment toward a child wasn’t something that did his likability factor any favors.
When Dean Nearly Took Castiel's Life
For the majority of their time together, a lot of fans wanted Dean and Castiel to become a couple - they were even dubbed “Destiel.” Understandably, many weren’t pleased when Dean proceeded to beat Castiel to an inch of his life while the latter took the punches.
Dean had been corrupted by the Mark of Cain but was still capable of making his own decisions. Rather than heeding Castiel’s warnings of letting his rage go, Dean took it out on him and beat Castiel badly. While the Mark was primarily to blame, fans still weren’t happy with what Dean did.