Rowena is a popular character on Supernatural. Since her first appearance in Season 10, she has been both an enemy and an ally of the Winchesters over the years. She's intelligent but manipulative and will use any means necessary to get what she wants.
She's had to learn some hard lessons in her thirst for power, especially when it comes to Lucifer. Nonetheless, the redheaded witch is undoubtedly a fan-favorite, even if she's committed several terrible acts.
10 Her Lack Of Regard For Human Life
From the very moment audiences met Rowena, she was sitting beneath two men in a hotel that were staked to the ceiling. When a drop of blood falls on her, she wipes it away without a second thought, looking annoyed. Rowena's introduction was brutal but it showed who she was as a diabolical and cunning witch that looked out for only herself.
9 When She Tried To Turn Crowley Against The Winchesters
Rowena is a master at manipulation. She always has an agenda. She tries connecting with her son, but it's not genuine, as she only wants something from him. In "The Hunter Games", she spies on a meeting of his with the Winchester brothers and later manages to trick Crowley into refusing to give the First Blade to the Winchesters, as Rowena wants it for herself. It's not the first or last time Rowena has conned to get what she wants, but it took a while for the Winchesters and Crowley to work together, and Rowena's attempts to break that alliance were selfish and brutal.
8 The Time She Tortured Olivette
After making Crowley feel guilty, he brings Rowena Olivette in chains, the high priestess of the Grand Coven. Rowena tortures her, thoroughly enjoying the task, as she gets the information she wants. Rowena nearly kills Olivette, but decides to turn her into a hamster instead, as she believed death was too kind a fate for the high priestess.
Rowena's taste for vengeance is dark, and this act showed that she was capable of awful things to get what she wanted.
7 Killed The One Person She Really Did Care About
Sam forces Rowena to remove the Mark of Cain from Dean after he broke their previous deal, and she agrees to it, as long as she gets her freedom in return. Unfortunately, her freedom means the death of someone she truly cares about, and though she is obviously conflicted at the thought of killing Oskar, she does so anyway. It does take a toll on her, but she still did it, putting her needs first. She got her freedom, and she got away with the "Book of the Damned", along with other items, and cast a dreadful spell on Castiel before she made her exit.
6 Used Her Own Grandson As A Gesture Of Revenge
Rowena has family issues, that's for sure. She uses her own grandson, Gavin, as a way to get back at Crowley for having to kill Oskar in a previous episode, a boy she truly cared about. Knowing that if she sends Gavin back to his own time he will meet his demise gives her more comfort than grief as she knows the toll it will take on Crowley.
Rowena cared more about vengeance than family, and this was pretty cold on her part.
5 The Time She Went After Dean
Rowena was in for a shock when neither of her spells worked on Dean. She had intended to kill him, but failed to succeed, given Dean beat up the men she sent after him and was immune to her spell that was meant to rip him apart courtesy of The Mark of Cain. Luckily for her, Dean decided to spare her. Even worse, she beat herself up and told Crowley that Dean was responsible in the hope that he would go after Dean. However, her plan backfires, and Rowena is served her karma.
4 She Was Far From Being 'Mother Of The Year'
Rowena uses Crowley and tries to manipulate him on more than one occasion. She frequently lets him know how much she hates him. She never acts maternal in any way; she always puts herself first. It's no wonder Crowley was bitter and resentful towards her. Though their tumultuous relationship often brought entertaining moments in the show, it's also heartbreaking. It's not until after Crowley sacrifices himself, and Rowena learns of his death, that she shows any remorse for how she acted towards him or the fact that she did care about her son in her own way.
3 Her Loyalty To The Wrong People
Rowena is always seeking power, wanting to advance further for her own gain. She made the mistake of pledging her loyalty to Lucifer, who had promised her that she would become his Queen. Of course, Lucifer was only using her, and he killed her after she had freed him.
Luckily, Rowena had a spell that brought her back to life, but it wasn't the last time Lucifer would kill her, and in the end, it would take a big toll on her. Rowena had to learn the hard way that power isn't everything.
2 When She Tried Getting Death's Attention
Rowena surprised even herself at her grief over the loss of her son, Crowley. In order to get him back, she begins killing reapers in order to get Death's attention. Once Sam and Dean figure out what Rowena's up to, with help from a reaper who isn't allowed to get her hands dirty, they intend to stop her, with Sam nearly paying the ultimate price with his life. Rowena, though, definitely went about getting Crowley back in the wrong way. She used the resources she had, but Rowena was playing with fire and things could have turned out much worse if Death hadn't shown Rowena the mercy she did.
1 She Didn't Care About Her Fiancé
In "LOTUS", Rowena is fighting with her fiancé, angered by the fact that he conducted a background check on her without her knowledge. In the midst of their argument, Crowley shows up, and promptly uses his powers to blow the man's head to smithereens. Instead of being devastated, or even horrified, Rowena appears to be joyful, declaring that it's the "nicest thing" Crowley's ever done for her. It's certainly dysfunctional, and it shows that Rowena didn't really love her significant other at all.
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