The older brother that never gives up, Dean Winchester is a fan favorite on things about Dean. He is both simple and mysterious, optimistic and doomed, and somehow he keeps getting up and going on to the next fight.
Dean is a warrior and a hero many times over and his triumphs are celebrated by characters all over the Supernatural universe. But there’s also plenty that doesn’t add up. Here are 10 things that don’t make sense about Dean Winchester.
Blind Loyalty To John
Throughout season 1, Dean is driven by the singular path of John’s instructions. He ridiculed Sam for not doing the same and then, later on, he’s all about free will and doing his own thing. When the angels tap him to be Michael’s vessel, he refuses to play ball.
In season 10, when they meet Chuck/God, he is blatantly disrespectful and angry that the entity had so much influence in their lives. When the British Men of Letters come to town promising safety and , he is skeptical, yet he was still blindly loyal to his father. This doesn’t make sense.
The Demon Deal To Save Sam
Season 2 was the first time that Sam died, stabbed in the spine by Jacob in Azazel’s cruel game. After the loss of their father in Season 1 as the result of a demon deal to save Dean, it makes no sense that he’d then make a deal to save Sam. He knew how it felt for Sam when their father made that deal.
He knew Sam would blame himself and with the clause that Sam dies if they try to break the deal, it made even less sense.
Didn’t Kill Ruby
At first, Ruby shows up with the promise to get Dean out of his deal, but Dean finds out soon after that there’s nothing she can really do to save him. After that, she convinces him that Sam needs her and that’s why Dean shouldn’t kill her.
This makes no sense at all. Dean knows that Sam can get by without the help of a demon, and if he’d killed her, he could have taken her knife and stopped the entire apocalypse before it ever started. In the end, he killed Ruby anyway and got the knife, but he could have done that in the first place and avoided a lot of heartache.
Lets Sam Jump Into The Pit
Before the plan for Sam to jump into the pit while possessed by Lucifer, Dean was ready trade his own life for Sam’s. He saw what would happen if Sam said “Yes” to Lucifer when he was sent to the future. He knew that the world would end. He refuses to let himself be used as Michael’s vessel.
Taking all of these points into consideration, it makes no sense that Dean would let Sam jump into the pit or even say “Yes” to Lucifer.
He’s Not In Prison
Dean is arrested more than once and narrowly escapes every time, usually with the caveat of faking his death to keep the cops off his back. But after the second time this happens, it makes no sense that the government doesn’t keep coming after him.
In one of these incidents, the brothers are accused of attempting to assassinate the president. Again, the escape centers on the government thinking they’re dead. Even after an act of terrorism, they still don’t make public enemy number one. What makes even less sense is that he continues to impersonate the FBI using the same classic rock aliases and yet somehow, he never gets caught.
He Keeps Fighting
Calling Dean determined would be a severe understatement. The world ends and he finally finds happiness with Lisa and Ben. After all the beating, being in hell, dying horribly in a hellhound mauling, he makes the decision to leave them behind. Then he dies several more times, gets stuck in purgatory, beaten up again and again, is shot, stabbed, and undergoes all kinds of other abuse.
When he finds a home at the Men of Letters bunker that’s warded and safe from every threat, it makes no sense for him to ever leave that safety again.
Bad Health Habits
For someone who is constantly active, Dean’s health habits are atrocious. Sam constantly hounds him about his diet and lack of exercise, but Dean still shovels in as much red meat, bacon, fried food, and pie as he can and washes it all down with bourbon and beer. He is never seen exercising.
On the contrary, Sam eats relatively healthy and has been pictured working out and running. Somehow, Dean can still run fast, jump high, and punch hard the same way that Sam can. This makes absolutely no sense. Logically, he should be overweight and barely able to climb a flight of stairs.
No Formal Fight Training
Dean is incredibly protective of his family and loved ones. He is willing to die for them, be tortured for them, and endure humiliation for them. After all the times he’s been in a fight that resulted in a brutal beating, it makes no sense that he never sought formal fight training. He appears content with powering forward through sheer force of will and instinct ... and a few good weapons.
Sam is usually the researcher and Dean gets a lot of downtime between cases. They joke about his adult entertainment habits and all the ways he enjoys wasting time, but he never considers using the considerable resources at his disposal to undergo formal fight training.
Relies Solely On Sam For Magic And Research
Every hunt has the potential for Dean to lose his brother. He occasionally helps with the research when they’re on a specific case, but most of the time he relies on Sam’s knowledge and Sam never stops learning. If he did ever lose Sam forever, he would likely have a rough time getting through the research he needed in time to save the day.
It makes no sense for Dean to continue to rely solely on Sam for the academic side of hunting. Sam can fight just as well as Dean, as shown during battles they fight in most cases. Logically, especially as a Men of Letters Legacy, Dean should be taking an equal share in the academics.
He’s Not A Drooling Psychotic Mess
In several story arcs, Sam’s psyche shows the strain of what he’s been through. Dean, on the other hand, remains stoic. When he refused to let the archangel Michael use him as a vessel in season 5, Zachariah and the other angels he encounters (including Castiel) imply that Michael “riding” him would leave him basically catatonic.
In the finale of season 13, Dean agrees to let Michael use him as a vessel in order to take out Lucifer once and for all, the very fight he avoided all those years before. Eventually, Jack kills Michael and Dean is the only person inhabiting his body once again. After everything he goes through, especially this, he is not catatonic. He appears to be the same Dean he always was and it makes no sense.