To start, Albus Dumbledore is not on my list. I always knew Dumbledore had to die. With the best wizard alive, Harry did not have any reason to confront Voldemort directly.
1. Dobby.
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Dobby is the death I cried the most. Dobby is a martyr. He is a slave in the second book, but he is brave enough to work against his owners to save Harry. Later, we know he is happy and full of socks working in Howards.
In the last book (and in movie seven), he appears when we think Harry is lost. Harry and his friends are in Malfoy's mansion as prisoners, and Bellatrix is torturing Hermione. Dobby arrives like a hero. Dobby saves everybody, but he gets killed by Bellatrix.
Dobby dies on the beach; it is heartbreaking. I remember myself crying all the time the book. Dobby deserved a better end, a happy one.
2. Fred.
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When you read a series of seven novels, you have some presentiments about the end of the novels. I always knew that one member of the Weasley family would die, but I never thought it would be one of the twins.
Weasley twins are amazing, brave, funny, and rebels. By the books and the movies, we got in love with them. Why did not Rolling kill Bill (we did not know him a lot), Charlie (we never saw him), or Percy (he is a jerk)? Why she has to hurt us so deeply?
3. Sirius.
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Harry finally finds a kind family member, his godfather Sirius Black. Sirius was unfairly imprisoned when Harry was a little boy. By the time, we discovered how much Sirius and James (Harry's father) loved each other. In books four and five, Sirius is a fugitive, but he always has time to take care of Harry.
In "Harry Potter and Order of the Phoenix" Harry makes a big mistake, and he goes to Voldemort's tramp. The result is Sirius dies, and Harry loses his only real family. In the end, Sirius has a sad life.
4. Lupin.
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Remus Lupin is another sad character. He is suffering lycanthropy all his life (he is a werewolf). The first time Rolling describes Lupin he is almost a homeless. He cannot get a good job because of his condition. When he finally finds the love with Tonks and has a kid, Edward, he dies in "Battle of Howards."
5. Harry.
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I can understand that Harry is the last Horcrux, but all the idea of Voldemort killing Harry, and Harry talking with Dumbledore in limbo is not good enough. It was too much, and it was not necessary.
Probably you have your list. I am not missing Snape in my list. I think he deserves his end.
By the way, each May 2nd, Rowling apologizes for one death in "Harry Potter" novels. She picked this date because it is the anniversary of the "Battle of Howards." So far, she said sorry for Dobby, Lupin, Fred and Snape.
