I think that every character that grew up with some sort of family that cared about them and treated them right (ex. Bruce Wayne, Peter Parker, Dick Grayson, etc.) can't win. They may have had extremely sad pasts, but only one hero can have the saddest past and it takes a lot to beat out all the other heroes. What exactly counts as someone's past is all opinion so I've stated where I think each character's "past" ends.
Possible Winners
Laura "X-23" Kinney
Past ends when: She joins the New X-Men
PRO: Cloned from Wolverine. Tortured because the head of the project she was made in hated Wolverine for killing his father. Her "mother"/creator cared about her, but almost never showed it and almost never made any move to try to stop them from hurting X-23. Later she was forced to kill her "mother" because of a trigger scent and the only way she knew to show that she cared was to ask "What is my mission?". She then became a prostitute for an abusive pimp.
CON: Her mother did care, though she rarely showed it and in the end tried to break her out.
Cassandra "Batgirl" Cain
Past ends when: She becomes Batgirl
PRO: Abused by her father. Made to kill at age 7. She then wandered the streets until saving Commissioner Gordon and becoming Batgirl. The way the man looked when she killed him haunted her until the reboot.
CON: Her father did love her in his own way and though it doesn't say what she did to live on the streets that part of her life becomes the same as many other characters.
Jason "Red Hood" Todd
Past ends when: He confronts Batman with the Joker.
PRO: He lived on the street alone because his mom cared more about drugs than him. After becoming Robin he and Bruce started fighting, escalating when he may or may not have pushed a rapist to his death. He later found out his mom was not really his biological mom and went to find his biological mom who was stealing money/drugs from a relief organization in an impoverished area. She betrayed Jason to the Joker so that she wouldn't get caught. The joker proceeded to beat him half to death with a crowbar and then blow him and his mother up. He was later resurrected and wandered the streets catatonically until Talia al Ghul found him. She put him into the Lazarus pits which woke him up then she gave him a bag and pushed him off a cliff after telling him that Bruce hadn't killed the Joker for what he did to Jason. Jason captured the Joker to try to force Batman to either kill the Joker or him. Being Batman, Bruce found a third option and threw a batarang that bounce off a wall and partially slit Jason's throat. Jason was replaced by another Robin.
CON: Bruce did truly care about him and he seemed to really enjoy life as Robin. After Talia found him he traveled around the world getting stronger.
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