Complex, messy, manipulative, and endlessly entertaining, Katherine Pierce is one of the best characters in The Vampire Diaries. She has a habit of popping up in Mystic Falls at exactly the wrong time to ruin the lives of not just her doppelgänger, but every supernatural creature (and a few humans) under the sun.
While she was set up as the big bad of season one, Katherine becomes easier to sympathize with as the show progresses – especially once it digs into her backstory. Katherine is the ultimate survivor, and her endless suffering is partly responsible for making her such an iconic (but sympathetic) villain.
Getting Trapped In The Tomb
Katherine narrowly escaped an even worse fate in 1864 when she managed to evade capture by the town locals. However, karma still comes for her a century and a half later. Her friend, Lucy Bennett, turns on her and helps Damon, Stefan, and Bonnie shut her back where she ought to have been all along: the tomb.
Her imprisonment isn't permanent, but enough to take its toll. Starved of blood, Katherine is weak and incapacitated. She's also forced to relive her previous traumas with Klaus when Elena comes to question their history together. Although she might deserve it, it's still the exact kind of isolation that she's tried to outrun for centuries.
Being Rejected By Elijah
Katherine doesn't love easily. While she's all too happy to toy with men, her one real love has always been Stefan. However, in season four she's revealed to have been in a secret relationship with Elijah while trying to retrieve the Cure.
This could easily be another classic case of Katherine manipulation, if not for the fact that she hands over the Cure and tells Elijah that she loves him. Despite that, he leaves for New Orleans and later rejects her. Rejection isn't something Katherine handles well – and she at least seems to handle this better than Stefan's constant rebukes – but it's tough not to feel bad for her losing the only true connection she's felt in centuries.
Elena Giving Her The Cure
Humanity is Katherine's worst nightmare. Not only is she afraid of death, but she relies on the strength and power of vampirism to get what she wants. So, when Elena stabs her with the Cure in the season four finale, it's only a matter of time until she melts down.
This happens very quickly. Katherine struggles with the fragility of being human. When the Cure is removed from her body and she begins to age rapidly, she struggles even more. She has always relied on herself to escape every situation. Once that option is eradicated, even Stefan struggles to hate her – and it's impossible not to empathize with her sudden loss of power.
Getting Caught Impersonating Elena
Doppelgängers are destined to hate each other – and Katherine more than lives up to the pattern. Elena has everything she's ever wanted. She's youthful, beautiful, and adored. Adored by Stefan, in particular, who Katherine has always loved but Elena has rejected in favor of Damon.
So, when the opportunity arises to step into Elena's shoes, she takes it. Nadia helps Katherine possess Elena's body in her final human moments. For a while, she lives life as a Gilbert, but is eventually caught and forced from Elena's body. For a while, she finally had the life she's always wanted. Even though it may have been an evil ploy, it's still upsetting to consider that all Katherine's ever wanted is safe, reliable love.
Losing Stefan
He may have been under her compulsion for the majority of their relationship in 1864, but Katherine really does love Stefan. Even after she flees the town for her own safety, she keeps tabs on him from afar over the years.
Becoming a vampire, however, breaks the hold Katherine once held over Stefan. He is able to see her for exactly who she really is – and he hates her. While she acts tough, Katherine would gladly love Stefan for real if he let her. She's overjoyed when they briefly reunite in season five, and devastated when he dismisses it as a mistake. If she and Stefan had had the chance to be together for real, there's a chance Katherine would've been softer and more sympathetic than the version fans know.
Giving Up Baby Nadia
Katherine was a young, unmarried woman when she fell pregnant in Bulgaria in the late 1400s. This was far from the cultural norm, so, when she gave birth, her father disowned her and gave the child up for adoption – despite Katherine begging otherwise.
The scenes in which her newborn is torn from her arms just seconds after giving birth are genuinely heartbreaking. It's the first time Katherine is really humanized in the show, and it explains a lot about the way she hardened her heart in the aftermath. What's more, it's her consequential exile to England that led to her meeting her biggest opponent, Klaus, in the first place.
Being Killed By Stefan (Twice)
As if losing him isn't enough, Stefan kills Katherine on two separate occasions. Her first 'permanent' death comes in season five, when he and the rest of Elena's loved ones realize Katherine has possessed Elena's body. Stefan stabs her, and is Katherine is notably upset when she remarks, "I guess this is how our love story ends."
Stefan goes on to kill her for a second time in season eight, dragging her in the path of hellfire after she intends to use it to destroy Mystic Falls. She's less personally offended on this occasion (after all, she is now the Queen of Hell) but it still hurts to be taken down by the person you love most.
Saying Goodbye To Nadia
For over 500 years, Katherine is unaware that the daughter she was forced to give up followed in her footsteps and became a vampire. Their reunion in season five is rocky – and Katherine tries her best to push her away – but she does ask her to stay in town so she can get to know her.
But she still loses Nadia all over again when she's bitten by Tyler Lockwood. Katherine could easily run – and live in Elena's body forever – but she ultimately puts Nadia first to come and say goodbye with a vision of the family they could have been. It's a full-circle moment for Katherine. Her first human moments in the show revolve around Nadia's birth, and those before her death show her finally prioritising someone over herself.
Klaus Killing Her Family
For all the evil she's done, plenty of external factors made Katherine the cold-hearted villain she is in the 21st century. One of the most pivotal moments in her descent is the slaughter of her entire family.
The man responsible is, of course, Klaus. Furious at Katherine evading him in England, he tracks the Petrovas down and murders them to make a point. It's undeniably Katherine's saddest scene – their deaths hit her right in one of the only human spots she has left. From the way she looks at pictures of her family even centuries later, this hurt her more than (almost) anything.
Spending 500 Years On The Run From Klaus
Katherine never asked to be born a doppelgänger – and she definitely never asked to be a part of Klaus' plans to break the Hybrid Curse. While she managed to escape him in 1492, turning herself into a vampire so her blood would be useless, she's forced to spend the rest of her life on the run.
Klaus is potentially the only one Katherine really fears. She has an undeniable skill for survival, but it's still torturous to spend literally half a millennium living on the edge. In the end, this is what makes Katherine the desperate, selfish, cruel person she is: the drive to live.