The famous Winchester brothers of SupernaturalDean and Sam, have had a life filled with tragedies. Dean, being the big brother, had tried to shield Sam from several misfortunes since they were kids, somehow making it easier for him.

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However, this led to Dean internally struggling with plenty of issues that he had no one to share with. This continued largely to their adulthood as well because even as adults, Dean kept most of his struggles to himself, not wanting to burden Sam. So, he endured a lot of woes and troubles that deeply pained him internally.

Going To Purgatory

Dean in purgatory looking sad in Supernatural

Dean Winchester has traveled to different timelines, worlds, and universes. One of his worst experiences was being stuck in Purgatory for a year. He and Cas were teleported there when they together killed Dick Roman. Almost as soon as they got there, Dean was left alone as Cas abandoned him.

What followed was a year of fighting against the bloodthirsty Leviathans and other vile creatures. Being a human, he was the primary target for all the monsters and so, he was always on the run for his life. Fortunately, he found some help in the form of Benny to fight off monsters together. When he finally reunites with Cas, he told him that he prayed to him every night, signifying how lonely and desperate he felt there.

Making Lisa And Ben Forget Him

A photograph of Ben and Lisa and Dean in Supernatural

Dean got a chance to live an "apple-pie life" for a year with Lisa and Ben and living such a long time with someone will make anyone care deeply for them. Crowley used them to blackmail Dean and put their lives in danger. Dean felt guilty for not being able to protect them and being the cause for messing up their normal lives.

So, Dean told Cas to make them forget him. The scene where he meets Lisa and Ben for the last time and they don't even recognize him is definitely hard to watch from Dean's perspective. Nothing is more important to Dean than the people he cares about and having two people he cared a lot for not recognizing him must have hurt real bad.

Castiel's Betrayal

Castiel looking serious in Supernatural

Until season 6, Castiel had become Dean's family and Dean himself said that numerous times. Dean trusted him almost blindly and considered him his best friend. So, when it was revealed that Cas had been lying to him for more than a year and he had colluded with Crowley to open up the gates of Purgatory, something in Dean breaks.

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Sam and Bobby were already doubting Cas' intentions but Dean defended his best friend until the very end, showing how much he believed that Cas could never lie to him or betray him. The moment he learns the truth, the hurt on his face is heartbreaking. After all this, he was still ready to forgive Cas and he pleaded with the angel to accept his misdeeds and turn back.

Mark Of Cain

Dean showing off his mark of Cain Supernatural

The storyline of Dean taking on the Mark of Cain started a chain of events that Dean probably would never be able to forget. He became the darkest version of himself after taking on the mark. He became a brutal killer and did several questionable things that likely haunted him for the rest of his existence.

Dean would lose control when he got his hands on the First Blade and a slight brawl ended in him killing a lot of people. It worsened to the point where he almost killed his best friend, Castiel when he tried to stop him from turning into a mindless killer. It also led him to become a demon. All these things only added up to the list of reasons for Dean to have a heavy conscience later on.

Losing Bobby

Bobby at the hospital in Supernatural

Bobby was basically the surrogate father of Sam and Dean. He cared for them as he would care for his own kids. Both Sam and Dean were definitely much closer to him than they were with John. Thus, losing him was a huge trauma for both of them.

However, it was a bigger tragedy for Dean than Sam because he had received some form of fatherly affection from Bobby that he had never gotten from John. So, losing him was much harder for Dean and it left him shaken to his core.

Sam Going To Lucifer's Cage

Sam looking angry in Supernatural

In the season 5 finale, Sam went out in a blaze of glory. He took control of his body, which was possessed by Lucifer, and plunged himself into the Cage in Hell. After losing Sam like that, Dean tried his best to get his brother back, and then, he went to live with Lisa and Ben as he promised to Sam.

However, he wasn't completely himself for the time he lived with them. He became a broken shell of a man, who seemed like a normal family man from the outset but the truth was that he couldn't sleep at night. Even when Sam's soul was retrieved, seeing him battling with his experiences in Lucifer's cage was extremely tough for Dean.

Going To Hell

Dean screaming in hell in Supernatural

Dean went to Hell at the end of season 3 and he stayed there for four months, but for him, it was 40 years. He was tortured brutally there by Alistair for 30 years, stopping only when Dean agreed to torture other souls himself. He was brought back in the season 4 premiere, "Lazarus Rising" by Castiel. 

Dean's time in Hell was certainly one of the hardest experiences of his life. He came back with PTSD-like symptoms and he wouldn't talk about it with anyone for the first few weeks. When he finally opened up about it to Sam, seeing him breaking down like that is by far one of the most tear-jerking moments of the show.

Losing Cas Multiple Times

Castiel crying while looking at Dean in Supernatural

Dean has witnessed Castiel's death plenty of times and with time, it only got harder and harder for him to deal with it. The first time it happened was at the end of season 4 when Dean was only grateful to him for his sacrifice. However, in the season 12 finale, when Cas was killed by Lucifer, Dean is outright devastated.

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He lost a lot of people that day, but somehow Castiel's death affected him the most. He lashes out at everything and everyone (even Sam) and he prays to God to bring him back, which is highly unusual for him. In short, he looks like he has lost everything. The final time Castiel dies in season 15 after confessing his romantic love, Dean is overcome with grief as he can be seen sitting with his head in his hands and sobbing.

Sam's Death In Season 2

Dean hugging Sam and crying in Supernatural

In season 2's finale, "All Hell Breaks Loose," Sam died for the first time by one of the other people chosen by Azazel, Jake. It is one of the best deaths in Supernatural. He goes on to die multiple times in the future, but because this was the first time, it affected Dean enormously.

This happened early in the show when Dean solely held himself responsible for Sam's well-being and wanted to protect him no matter what. His reaction to Sam's death is heartbreaking and later when he talks to Sam's corpse will bring any Dean fan to tears. Dean was so devastated that he sold his soul to bring Sam back to life. This eventually led to Dean going to hell at the end of season 3.

Mary's Death When He Was A Kid

Mary looking distrustful in Supernatural

Dean's life probably would have been a lot different had Mary not been burned on the ceiling of Sam's nursery, when Dean was four years old. The incident completely changed the course of his life.

It is a no-brainer that Dean Winchester is carrying his childhood trauma, which is negatively affecting his adult life. This childhood trauma started with Mary's death. He had to grow up quickly to take care of his brother, his father became distant and treated him more like a soldier, and he never had a normal childhood like most other kids.

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