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Isaac Grossman is the villain protagonist of The Origin of Laughing Jack and arguably the posthumous overarching antagonist of the Laughing Jack mythos.
Isaac Lee Grossman was a lonely boy living in 1800s London England with abusive parents. His father was an alcoholic misogynist who beat and raped his wife on a regular basis, while his mother took her anger and grief out on Isaac and called him a "useless worm". His abysmal life caught the attention of a guardian angel who created a not so imaginary friend for him named Laughing Jack, who came to Isaac in a box. The two quickly became friends, but after Jack accidentally killed a cat and Isaac got blamed for it, Isaac was sent off to a boarding school, leaving Jack to be stuck back in his box, unable to be freed until someone opened it.
13 years later, Mr. Grossman accidentally beat his wife to death and was executed for it. With both his parents dead, the 20 year old Isaac inherited their house. Unfortunately, Isaac had come to believe that Jack was just an imaginary friend during his time at boarding school. Because of this, he broke his promise to release Jack from his box.
Driven mad due to the abuse and unhappy life he had endured, Isaac became a serial killer who would torture and murder people in front of Jack's box. His first victim was a woman who rejected his advances. After a failed attempt to rape her, Isaac caved in her skull with a candlestick holder before turning her remains into an armchair. His second victim was a child aged 5–6 years old. Isaac picked him out as retribution for the child "making a nasty face" at him. Isaac tortured and murdered the boy. The third victim was a blind old woman Isaac invited over for tea and made sit in the human armchair until she realized it was constructed from human bones, after which, he allowed her to run around trying to escape the house before falling down the stairs, after which Isaac finished her off with an icepick through her eye. The fourth victim was a little girl Isaac force fed broken glass to before using her stomach as a punching bag.
As the weeks went by, Isaac continued to torture and murder people, prompting Jack, who was made to adapt and develop with Isaac's personality, to become as dark and sadistic as Isaac himself. One night, the shelf holding the box fell down. Isaac discovered the box and accidentally released Jack. Disgruntled with his former friend for forgetting about him, Jack tortured and killed Isaac before going to terrorize and kill children all over the world.
It's rumored that the police eventually found Isaac's remains in December of that year months later. Strangely, despite his horrendous murder, Isaac's rotten corpse looked happy.
Isaac Grossman started off as a friendly young boy who wanted friends and was very happy with Laughing Jack. However, he was mentally unwell due to his upbringing and laughed at seeing a cat violently killed.
As an adult, he became a psychopathic serial killer as a result of the lonely life he had as well as the abuse he had suffered from his parents and the boarding school. He became incredibly dark and sadistic, torturing children to death and making furniture from the corpses of his victims. He demonstrated no remorse for any of his actions and was noted to have had a black heart full of rage and hatred. He was also a misogynist, as he called a woman a "stupid whore" and tried to rape her after she rejected his sexual advances.