Heroes must take risks to get things done. Dean Winchester is no exception, and he makes some borderline crazy choices in Supernatural. They work out often enough that season 15 has poked fun at it with two episodes about luck, but even when they work out it makes the viewer nervous.
What’s worse is that Dean is often gambling with cosmic forces. He’s not just risking getting caught by the cops or something, he’s risking death or worse. Dean’s trademark boldness and determination in the face of these risks make him the hero fans love. Here are some of the riskiest decisions Dean’s made in the show.
10 Dying to Meet Death
This particular choice was on the stupid side of risky. Dean wanted to get Sam’s soul back from hell partially out of fear of the new Sam. So he paid someone to give him a lethal injection and then bring him back from the dead, just so he could talk to Death about retrieving the soul. It’s debatable whether this was riskier than his later attempt to summon Death and bind him, but Dean had no guarantee that Death would agree to help him, or even agree to let him leave when the doctor revived him. He could’ve died with a soulless Sam still roaming around on Earth.
9 Going to the Michael-Lucifer Fight With No Plan
Dean spent all of season 5 trying to prevent this fight. He and Sam’s final plan to beat Lucifer was for Sam to say yes and then jump into Lucifer’s cage willingly. When that failed, Dean didn’t come up with any better plans. He rolled up into Stull Cemetery with no way of actually beating Lucifer or Michael.
He just wanted to talk to Sam however briefly. Both Castiel and Bobby got killed in the process, and Dean got a beatdown. It was mostly sheer dumb luck that Sam finally regained enough control to open the cage and jump in.
8 Swallowing Phoenix Ash
While this doesn’t necessarily stick out as one of his riskier moves, it’s actually terrifying on second thought. Dean pulled a clever trick in season 6, getting Eve to ingest the lethal phoenix ash by swallowing it himself and persuading her to bite him. But he didn’t actually know that it would work. What if the phoenix ash didn’t really get into his bloodstream? What if it didn’t prevent her from turning him into a monster? And what if the ashes were toxic to humans? There were so many ways this could’ve gone wrong, but this gamble fortunately paid off.
7 Acting as a Bomb for Amara
Fighting God’s sister will necessarily lead to some desperate measures. If this plan with the soul-bomb had worked, it would’ve guaranteed Dean’s death. Yet it was still risky in that if it didn’t work, everyone on the planet could die right along with him. And the magic for it was fairly experimental, since no one had ever tried to kill God’s sister. This particular gamble didn’t actually pay off, and Amara had to be defeated by other means. Lucky for Dean that didn’t involve the death of himself or any of his friends.
6 Deliberately Going to Prison
Sam and Dean were on the wrong side of the law all the way back in season 1. Their crimes stack up, some of them for good reasons and some for bad. So actually letting themselves get caught in season 2 was incredibly dangerous. They were pretty much guaranteed to get convictions if they went to trial, they wouldn’t be hunting monsters anymore, and worse still they might be trapped in a haunted prison. They did it to help hunt a ghost and return a favor, but escaping from a prison is no simple task even with help.
5 Summoning Castiel
Castiel turned out to be a fan-favorite and a hero in his own right. But the boys didn’t know he was a good guy when Dean was mysteriously pulled from hell. All Dean knew was that something had the power to yank him out of hell and that even demons were terrified of it.
He also knew that it burned out Pamela’s eyes (though this was unintentional on Castiel’s part, and he did try to warn her). Summoning an unknown entity with the power to steal a soul from hell and terrify demons is a scary proposition, but he desperately needed to know what was happening.
4 Trapping Raphael
Archangels started out as terrifying creatures on supernatural. Castiel’s power as a lower angel was enough to have demons shaking in their shoes, so his superiors were a huge threat. Antagonizing one by trapping it in holy fire, especially while said angels were trying to hunt him down, was not necessarily the smartest move. Dean took this risk for Castiel to help him get answers about God and the apocalypse, and they did gather some significant information. Better still, Dean walked away without being taking to Michael or coerced into being a vessel.
3 Accepting the Mark of Cain
This was another of Dean’s risks that crossed the line into stupid. He was so fixated on killing Abaddon at any cost that he literally accepted any cost. He accepted the bloodlust, the loss of control, and eventually becoming a demon. This risk also led to him almost killing Sam and letting Death throw Dean out into the universe where he could never hurt anyone for eternity. While he did get the job done killing Abaddon, the price was ultimately way too high, and he’d have been better off if he kept looking for alternatives.
2 Trusting Crowley with Killing Dick Roman
The boys needed the “three bloods of the fallen” to kill the head of the leviathans. That included Crowley as the King of Hell and therefore fallen humans. The trick is, they didn’t actually see him extract the blood. He had it already bottled up so they couldn’t know for sure if it was his or not. It wasn’t the first time they’d worked with Crowley, but working with Crowley was always dangerous. He had an offer from Dick Roman that the boys couldn’t be sure he wouldn’t put before them and the world. Fortunately, Crowley saw Dick and the leviathans as the bigger problem.
1 Trusting Gadreel with Sam
Dean has made a habit of defying death. He’s particularly adamant about keeping Sam alive even when the consequences are dire. So sending out a random call to any angel listening (when many of them hate his guts) was not an unusual risk for him. However, he’d planned on just having them heal Sam if possible. He didn’t expect it to turn into having an angel possess Sam, especially when that can’t be done against his will. Dean tricked his brother into accepting possession by angel he’d just met. This ended badly, precipitating the death of Kevin Tran among other things.
NEXT: Supernatural: 5 Old Characters We Miss (& 5 That Should Probably Be Phased Out)