Warning: This list includes mentions of violence, sexual assault, and murder.When it comes to the characters on The Handmaid’s Tale and the worst things they’ve done, it’s really difficult to choose for some people. Even characters like June who fans sympathize with have done heinous things, like her brutal killing of Commander Fred Waterford.

But looking back, certain things each character has done have been especially awful. That’s saying a lot in a society like Gilead where torture, maiming, and even murder are all part of everyday life.

June Osborne: Beat And Killed Fred

A close up of June from The Handmaid's Tale looking upset

By far, the most awful thing June has done was killing Commander Fred Waterford. While it’s tough to fault her for feeling such passionate anger, murder is never the answer. What’s more, she killed him in the most brutal fashion. She had several other escaped handmaids by her side, and they chased and hunted him down like an animal, then beat and tortured him to death.

The fact that she then severed his finger and mailed it to Serena Joy, then refused to clean the blood from her face and arms the following day, made it even worse. It was as though she felt a sense of relief after committing the act, and did not feel any remorse about it at all.

Serena Joy Waterford: Used Hannah Against June

Serena Joy Waterford from The Handmaid's Tale dressed in black with a black veil, looking down.

Serena Joy Waterford – one of the most villainous characters in The Handmaid’s Tale - is an evil, ruthless person who doesn’t always come across as such. It’s easy to forget that she is not only a high-ranking commander’s wife in Gilead, but she is also one of the key architects in the creation of the society.

From torturing June to sitting by while Fred raped the handmaid in an attempt to induce labor, it seems there are no lengths Serena won’t go to get what she wants. But one of her worst acts was in commissioning Hannah to offer her flowers during Fred’s televised funeral, knowing June would be watching. It was cruel, calculating, and a low blow, even despite the circumstances.

Fred Waterford: Raped June

The Handmaids Tale Fred and Serena Season 3 Liars

Commander Fred Waterford raped June every time the ceremony was performed in an attempt to impregnate her. But the one particularly awful scene was when he raped her for no reason other than because he heard it’s a natural way to help induce labor.

There are no mincing words: it was a ritualized rape and done for purely selfish reasons, more so than any usual “ceremony.” It left June feeling even more like a receptacle than a human. And while it was Serena’s idea and she sat idly by while it happened, it remains the worst thing Fred has done.

Aunt Lydia: Ordered Mutilation Of Ofglen

Ofglen in a white hospital gown holding her stomach, Aunt Lydia looking on in a scene from The Handmaid's Tale

After discovering that Ofglen (Emily) was a lesbian or, as they were called in Gilead, a gender traitor, and that she was in a relationship with another woman, Aunt Lydia was livid. She punished Ofglen brutally, first by having her partner killed as per one of the most terrifying laws in The Handmaid’s Tale.

Then, she ordered a medical procedure to remove the part of Emily’s female anatomy that provides a sense of pleasure, ensuring she would never engage in sexual activity for personal gain. It was the cruelest of punishments Aunt Lydia had ever ordered, even including death.

Commander Warren Putnam: Assaulted Esther

A close-up of Commander Putnam looking scary, standing in a dark room

While nothing graphic was shown on screen, it was implied that Commander Warren Putnam sexually assaulted Esther. After Mrs. Putnam agreed for Esther to be their new handmaid, he asked Aunt Lydia to leave them alone so he could “get to know her better.”

He closed the door and began to weirdly feed her chocolates as if she was a baby or child. It was a disgusting scene that made viewers uncomfortable and showed his true colors. Even after what he did to Janine, this act takes the cake. Esther’s reaction towards Janine after the fact suggests that she thought Janine knew exactly what Commander Putnam was like and set her up to be in an especially unbearable situation.

Esther: Poisoned Herself And Janine

Esther poisoned in The Handmaids Tale Season 5

Esther – one of the best characters introduced after season 1 of The Handmaid’s Tale - went through a lot at such a young age, first being sent to become a wife, then being forced to become a handmaid. While Janine did her best to help the young woman, Esther resented Janine and the fact that she gave in to the rules of Gilead and obeyed every command.

When Esther believed Janine was using her to get closer to her biological daughter, Esther did the unthinkable. She poisoned both Janine and herself, leaving them coughing up blood and near death.

Janine: Threatened To Harm Baby Angela

Janine standing with Aunt Lydia in her handmaid garb in a scene from The Handmaid's Tale

It was understandable what state of mind Janine would be in after being tortured and forced to live a life of servitude, repeatedly being raped and used to create a baby. But when she realized her commander’s promises of leaving his wife to run away with her and their baby were all a ruse, she did the unthinkable.

She grabbed baby Angela and threatened to kill both herself and the child. It was one of the plot twists on The Handmaid’s Tale that fans didn’t see coming. Thankfully, June was able to literally talk her off the ledge. Fans felt sympathetic towards Janine and didn’t actually think she would go through with it. Nonetheless, even the mere mention of hurting a child is deplorable.

Nick Blaine: Worked As A Mole

Nick standing with his arms folded in The Handmaid's Tale

Nick Blaine is one of the most polarizing characters. While he goes out of his way and risks his reputation and even life to help June, he also sits idly by while awful things happen to others. In some cases, he’s directly involved with the acts.

While fans are on the side of Nick working against Gilead, working against the totalitarian society is also the worst thing he has done. Where his true allegiances do, and will, lie, remains to be seen. Nonetheless, Nick has proven that he might not be trustworthy to either side, conflicted by what will be best for him in the end.

NEXT: The Saddest Deaths In The Handmaid’s Tale, Ranked